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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Electroconductive Hydrogel Based on Functional Poly(Ethylenedioxy
Thiophene)</title>
<author><name sortKey="Mawad, Damia" sort="Mawad, Damia" uniqKey="Mawad D" first="Damia" last="Mawad">Damia Mawad</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="aff2">School of Materials Science and Engineering,<institution>UNSW Australia</institution>
, Sydney, New South Wales 2052,<country>Australia</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Artzy Schnirman, Arbel" sort="Artzy Schnirman, Arbel" uniqKey="Artzy Schnirman A" first="Arbel" last="Artzy-Schnirman">Arbel Artzy-Schnirman</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Tonkin, Joanne" sort="Tonkin, Joanne" uniqKey="Tonkin J" first="Joanne" last="Tonkin">Joanne Tonkin</name>
<affiliation><nlm:aff id="aff3">Faculty of Medicine,<institution>Imperial College London</institution>
, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Ramos, Jose" sort="Ramos, Jose" uniqKey="Ramos J" first="Jose" last="Ramos">Jose Ramos</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="aff4">POLYMAT, Bionanoparticles Group,<institution>University of the Basque Country UPV/EHU</institution>
, Donostia-San Sebastián 20018,<country>Spain</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Inal, Sahika" sort="Inal, Sahika" uniqKey="Inal S" first="Sahika" last="Inal">Sahika Inal</name>
<affiliation><nlm:aff id="aff5">Department of Bioelectronics,<institution>Ecole Nationale Superieure des Mines, CMP-EMSE, MOC</institution>
, Gardanne 13541,<country>France</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Mahat, Muzamir X0a M" sort="Mahat, Muzamir X0a M" uniqKey="Mahat M" first="Muzamir X0a M." last="Mahat">Muzamir X0a M. Mahat</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Darwish, Nadim" sort="Darwish, Nadim" uniqKey="Darwish N" first="Nadim" last="Darwish">Nadim Darwish</name>
<affiliation><nlm:aff id="aff6">Nanochemistry Research Institute, Department of Chemistry, Faculty of Science and Engineering,<institution>Curtin University</institution>
, Perth, Western Australia 6102,<country>Australia</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Zwi Dantsis, Limor" sort="Zwi Dantsis, Limor" uniqKey="Zwi Dantsis L" first="Limor" last="Zwi-Dantsis">Limor Zwi-Dantsis</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Malliaras, George G" sort="Malliaras, George G" uniqKey="Malliaras G" first="George G." last="Malliaras">George G. Malliaras</name>
<affiliation><nlm:aff id="aff5">Department of Bioelectronics,<institution>Ecole Nationale Superieure des Mines, CMP-EMSE, MOC</institution>
, Gardanne 13541,<country>France</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Gooding, J Justin" sort="Gooding, J Justin" uniqKey="Gooding J" first="J. Justin" last="Gooding">J. Justin Gooding</name>
<affiliation><nlm:aff id="aff7">School of Chemistry, Australian Centre for NanoMedicine and ARC Centre of Excellence in Convergent BioNano Science and Technology,<institution>University of New South Wales</institution>
, Sydney, New South Wales 2052,<country>Australia</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Lauto, Antonio" sort="Lauto, Antonio" uniqKey="Lauto A" first="Antonio" last="Lauto">Antonio Lauto</name>
<affiliation><nlm:aff id="aff8">Biomedical Engineering and Neuroscience (BENS) Research Group,<institution>University of Western Sydney</institution>
, Penrith, New South Wales 2751,<country>Australia</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Stevens, Molly M" sort="Stevens, Molly M" uniqKey="Stevens M" first="Molly M." last="Stevens">Molly M. Stevens</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PMC</idno>
<idno type="pmid">27656042</idno>
<idno type="pmc">5024651</idno>
<idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5024651</idno>
<idno type="RBID">PMC:5024651</idno>
<idno type="doi">10.1021/acs.chemmater.6b01298</idno>
<date when="2016">2016</date>
<idno type="wicri:Area/Pmc/Corpus">000690</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000690</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Electroconductive Hydrogel Based on Functional Poly(Ethylenedioxy
Thiophene)</title>
<author><name sortKey="Mawad, Damia" sort="Mawad, Damia" uniqKey="Mawad D" first="Damia" last="Mawad">Damia Mawad</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="aff2">School of Materials Science and Engineering,<institution>UNSW Australia</institution>
, Sydney, New South Wales 2052,<country>Australia</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Artzy Schnirman, Arbel" sort="Artzy Schnirman, Arbel" uniqKey="Artzy Schnirman A" first="Arbel" last="Artzy-Schnirman">Arbel Artzy-Schnirman</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Tonkin, Joanne" sort="Tonkin, Joanne" uniqKey="Tonkin J" first="Joanne" last="Tonkin">Joanne Tonkin</name>
<affiliation><nlm:aff id="aff3">Faculty of Medicine,<institution>Imperial College London</institution>
, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Ramos, Jose" sort="Ramos, Jose" uniqKey="Ramos J" first="Jose" last="Ramos">Jose Ramos</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="aff4">POLYMAT, Bionanoparticles Group,<institution>University of the Basque Country UPV/EHU</institution>
, Donostia-San Sebastián 20018,<country>Spain</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Inal, Sahika" sort="Inal, Sahika" uniqKey="Inal S" first="Sahika" last="Inal">Sahika Inal</name>
<affiliation><nlm:aff id="aff5">Department of Bioelectronics,<institution>Ecole Nationale Superieure des Mines, CMP-EMSE, MOC</institution>
, Gardanne 13541,<country>France</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Mahat, Muzamir X0a M" sort="Mahat, Muzamir X0a M" uniqKey="Mahat M" first="Muzamir X0a M." last="Mahat">Muzamir X0a M. Mahat</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Darwish, Nadim" sort="Darwish, Nadim" uniqKey="Darwish N" first="Nadim" last="Darwish">Nadim Darwish</name>
<affiliation><nlm:aff id="aff6">Nanochemistry Research Institute, Department of Chemistry, Faculty of Science and Engineering,<institution>Curtin University</institution>
, Perth, Western Australia 6102,<country>Australia</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Zwi Dantsis, Limor" sort="Zwi Dantsis, Limor" uniqKey="Zwi Dantsis L" first="Limor" last="Zwi-Dantsis">Limor Zwi-Dantsis</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Malliaras, George G" sort="Malliaras, George G" uniqKey="Malliaras G" first="George G." last="Malliaras">George G. Malliaras</name>
<affiliation><nlm:aff id="aff5">Department of Bioelectronics,<institution>Ecole Nationale Superieure des Mines, CMP-EMSE, MOC</institution>
, Gardanne 13541,<country>France</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Gooding, J Justin" sort="Gooding, J Justin" uniqKey="Gooding J" first="J. Justin" last="Gooding">J. Justin Gooding</name>
<affiliation><nlm:aff id="aff7">School of Chemistry, Australian Centre for NanoMedicine and ARC Centre of Excellence in Convergent BioNano Science and Technology,<institution>University of New South Wales</institution>
, Sydney, New South Wales 2052,<country>Australia</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Lauto, Antonio" sort="Lauto, Antonio" uniqKey="Lauto A" first="Antonio" last="Lauto">Antonio Lauto</name>
<affiliation><nlm:aff id="aff8">Biomedical Engineering and Neuroscience (BENS) Research Group,<institution>University of Western Sydney</institution>
, Penrith, New South Wales 2751,<country>Australia</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Stevens, Molly M" sort="Stevens, Molly M" uniqKey="Stevens M" first="Molly M." last="Stevens">Molly M. Stevens</name>
<affiliation><nlm:aff id="aff1">Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">Chemistry of Materials</title>
<idno type="ISSN">0897-4756</idno>
<idno type="eISSN">1520-5002</idno>
<imprint><date when="2016">2016</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="cm-2016-01298t_0007" id="ab-tgr1"></graphic>
</p>
<p>Poly(ethylene
dioxythiophene) with functional pendant groups bearing
double bonds is synthesized and employed for the fabrication of electroactive
hydrogels with advantageous characteristics: covalently cross-linked
porous 3D scaffolds with notable swelling ratio, appropriate mechanical
properties, electroactivity in physiological conditions, and suitability
for proliferation and differentiation of C2C12 cells. This is a new
approach for the fabrication of conductive engineered constructs.</p>
</div>
</front>
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</TEI>
<pmc article-type="research-article" xml:lang="EN"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Chem Mater</journal-id>
<journal-id journal-id-type="iso-abbrev">Chem Mater</journal-id>
<journal-id journal-id-type="publisher-id">cm</journal-id>
<journal-id journal-id-type="coden">cmatex</journal-id>
<journal-title-group><journal-title>Chemistry of Materials</journal-title>
</journal-title-group>
<issn pub-type="ppub">0897-4756</issn>
<issn pub-type="epub">1520-5002</issn>
<publisher><publisher-name>American Chemical Society</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">27656042</article-id>
<article-id pub-id-type="pmc">5024651</article-id>
<article-id pub-id-type="doi">10.1021/acs.chemmater.6b01298</article-id>
<article-categories><subj-group><subject>Article</subject>
</subj-group>
</article-categories>
<title-group><article-title>Electroconductive Hydrogel Based on Functional Poly(Ethylenedioxy
Thiophene)</article-title>
</title-group>
<contrib-group><contrib contrib-type="author" corresp="yes" id="ath1"><name><surname>Mawad</surname>
<given-names>Damia</given-names>
</name>
<xref rid="cor1" ref-type="other">*</xref>
<xref rid="aff1" ref-type="aff">†</xref>
<xref rid="aff2" ref-type="aff">‡</xref>
<xref rid="notes-2" ref-type="notes">¶</xref>
</contrib>
<contrib contrib-type="author" id="ath2"><name><surname>Artzy-Schnirman</surname>
<given-names>Arbel</given-names>
</name>
<xref rid="aff1" ref-type="aff">†</xref>
<xref rid="notes-2" ref-type="notes">¶</xref>
</contrib>
<contrib contrib-type="author" id="ath3"><name><surname>Tonkin</surname>
<given-names>Joanne</given-names>
</name>
<xref rid="aff3" ref-type="aff">§</xref>
</contrib>
<contrib contrib-type="author" id="ath4"><name><surname>Ramos</surname>
<given-names>Jose</given-names>
</name>
<xref rid="aff1" ref-type="aff">†</xref>
<xref rid="aff4" ref-type="aff">∥</xref>
</contrib>
<contrib contrib-type="author" id="ath5"><name><surname>Inal</surname>
<given-names>Sahika</given-names>
</name>
<xref rid="aff5" ref-type="aff">⊥</xref>
</contrib>
<contrib contrib-type="author" id="ath6"><name><surname>Mahat</surname>
<given-names>Muzamir
M.</given-names>
</name>
<xref rid="aff1" ref-type="aff">†</xref>
</contrib>
<contrib contrib-type="author" id="ath7"><name><surname>Darwish</surname>
<given-names>Nadim</given-names>
</name>
<xref rid="aff6" ref-type="aff">#</xref>
</contrib>
<contrib contrib-type="author" id="ath8"><name><surname>Zwi-Dantsis</surname>
<given-names>Limor</given-names>
</name>
<xref rid="aff1" ref-type="aff">†</xref>
</contrib>
<contrib contrib-type="author" id="ath9"><name><surname>Malliaras</surname>
<given-names>George G.</given-names>
</name>
<xref rid="aff5" ref-type="aff">⊥</xref>
</contrib>
<contrib contrib-type="author" id="ath10"><name><surname>Gooding</surname>
<given-names>J. Justin</given-names>
</name>
<xref rid="aff7" ref-type="aff">∇</xref>
</contrib>
<contrib contrib-type="author" id="ath11"><name><surname>Lauto</surname>
<given-names>Antonio</given-names>
</name>
<xref rid="aff8" ref-type="aff">○</xref>
</contrib>
<contrib contrib-type="author" corresp="yes" id="ath12"><name><surname>Stevens</surname>
<given-names>Molly M.</given-names>
</name>
<xref rid="cor2" ref-type="other">*</xref>
<xref rid="aff1" ref-type="aff">†</xref>
</contrib>
<aff id="aff1"><label>†</label>
Department of Materials, Department of Bioengineering, Institute of Biomedical Engineering,<institution>Imperial College London</institution>
, Prince Consort Road, London SW7 2AZ,<country>United Kingdom</country>
</aff>
<aff id="aff2"><label>‡</label>
School of Materials Science and Engineering,<institution>UNSW Australia</institution>
, Sydney, New South Wales 2052,<country>Australia</country>
</aff>
<aff id="aff3"><label>§</label>
Faculty of Medicine,<institution>Imperial College London</institution>
, London SW7 2AZ,<country>United Kingdom</country>
</aff>
<aff id="aff4"><label>∥</label>
POLYMAT, Bionanoparticles Group,<institution>University of the Basque Country UPV/EHU</institution>
, Donostia-San Sebastián 20018,<country>Spain</country>
</aff>
<aff id="aff5"><label>⊥</label>
Department of Bioelectronics,<institution>Ecole Nationale Superieure des Mines, CMP-EMSE, MOC</institution>
, Gardanne 13541,<country>France</country>
</aff>
<aff id="aff6"><label>#</label>
Nanochemistry Research Institute, Department of Chemistry, Faculty of Science and Engineering,<institution>Curtin University</institution>
, Perth, Western Australia 6102,<country>Australia</country>
</aff>
<aff id="aff7"><label>∇</label>
School of Chemistry, Australian Centre for NanoMedicine and ARC Centre of Excellence in Convergent BioNano Science and Technology,<institution>University of New South Wales</institution>
, Sydney, New South Wales 2052,<country>Australia</country>
</aff>
<aff id="aff8"><label>○</label>
Biomedical Engineering and Neuroscience (BENS) Research Group,<institution>University of Western Sydney</institution>
, Penrith, New South Wales 2751,<country>Australia</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor1"><label>*</label>
E-mail: <email>Damia.mawad@unsw.edu.au</email>
.</corresp>
<corresp id="cor2"><label>*</label>
E-mail: <email>m.stevens@imperial.ac.uk</email>
.</corresp>
</author-notes>
<pub-date pub-type="epub"><day>25</day>
<month>07</month>
<year>2016</year>
</pub-date>
<pub-date pub-type="ppub"><day>13</day>
<month>09</month>
<year>2016</year>
</pub-date>
<volume>28</volume>
<issue>17</issue>
<fpage>6080</fpage>
<lpage>6088</lpage>
<history><date date-type="received"><day>31</day>
<month>03</month>
<year>2016</year>
</date>
<date date-type="rev-recd"><day>25</day>
<month>07</month>
<year>2016</year>
</date>
</history>
<permissions><copyright-statement>Copyright © 2016 American Chemical Society</copyright-statement>
<copyright-year>2016</copyright-year>
<copyright-holder>American Chemical Society</copyright-holder>
<license><license-p>This is an open access article published under a Creative Commons Attribution (CC-BY) <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html">License</ext-link>
, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.</license-p>
</license>
</permissions>
<abstract><p content-type="toc-graphic"><graphic xlink:href="cm-2016-01298t_0007" id="ab-tgr1"></graphic>
</p>
<p>Poly(ethylene
dioxythiophene) with functional pendant groups bearing
double bonds is synthesized and employed for the fabrication of electroactive
hydrogels with advantageous characteristics: covalently cross-linked
porous 3D scaffolds with notable swelling ratio, appropriate mechanical
properties, electroactivity in physiological conditions, and suitability
for proliferation and differentiation of C2C12 cells. This is a new
approach for the fabrication of conductive engineered constructs.</p>
</abstract>
<custom-meta-group><custom-meta><meta-name>document-id-old-9</meta-name>
<meta-value>cm6b01298</meta-value>
</custom-meta>
<custom-meta><meta-name>document-id-new-14</meta-name>
<meta-value>cm-2016-01298t</meta-value>
</custom-meta>
<custom-meta><meta-name>ccc-price</meta-name>
<meta-value></meta-value>
</custom-meta>
</custom-meta-group>
</article-meta>
</front>
<body><sec id="sec1"><title>Introduction</title>
<p>Conducting polymers
(CPs) have gained popularity in recent years
as components of complex systems designed to electrically communicate
with biological environments.<sup><xref ref-type="bibr" rid="ref1">1</xref>
</sup>
Indeed,
CPs provide new ways to communicate with cells, tissues, and other
multicellular structures as they can avoid the mechanical mismatch
of harder inorganic based materials and are also able to exhibit ionic
in addition to electronic conductivity.<sup><xref ref-type="bibr" rid="ref2">2</xref>
</sup>
This is highlighted by the use of CPs as active components across
a broad range of biotic/abiotic interfaces, with pioneering examples
including the electronic plant,<sup><xref ref-type="bibr" rid="ref3">3</xref>
</sup>
organic
electrochemical transistor,<sup><xref ref-type="bibr" rid="ref4">4</xref>
</sup>
neural cell
membrane mimicking electrode,<sup><xref ref-type="bibr" rid="ref5">5</xref>
</sup>
and multiplex
immunoassay biosensor.<sup><xref ref-type="bibr" rid="ref6">6</xref>
</sup>
Among the many
forms they have been processed into, such as multilayered films,<sup><xref ref-type="bibr" rid="ref7">7</xref>
,<xref ref-type="bibr" rid="ref8">8</xref>
</sup>
fibers,<sup><xref ref-type="bibr" rid="ref9">9</xref>
</sup>
and sponges,<sup><xref ref-type="bibr" rid="ref10">10</xref>
</sup>
CPs are being considered as a structural material for the
fabrication of electroconductive hydrogels.<sup><xref ref-type="bibr" rid="ref11">11</xref>
</sup>
In tissue engineering, mimicking the properties of the native extracellular
matrix such as its hydrated nature is essential. In the case of electro-responsive
organs such as the heart and nervous system, the engineered scaffold
would also be required to be electrically conductive to reinstate
the electronic functionality to the tissue.<sup><xref ref-type="bibr" rid="ref12">12</xref>
</sup>
Nevertheless, the fabrication of electroconductive hydrogels based
on CPs has proven challenging. CPs exhibit (i) high stiffness due
to their inherently rigid backbone containing conjugated double bonds,<sup><xref ref-type="bibr" rid="ref13">13</xref>
,<xref ref-type="bibr" rid="ref14">14</xref>
</sup>
(ii) a hydrophobic nature due to the aromatic rings in the backbone,
and (iii) unwanted cross-links induced by π–π stacking
of the chains.<sup><xref ref-type="bibr" rid="ref15">15</xref>
</sup>
In contrast, a 3D hydrogel
network consists of cross-linked hydrophilic polymers with high water
content, exhibits elastic behavior, and has porous internal structures.<sup><xref ref-type="bibr" rid="ref16">16</xref>
,<xref ref-type="bibr" rid="ref17">17</xref>
</sup>
Here, we report a new fabrication approach for a functional poly(ethylene
dioxythiophene) (PEDOT) based hydrogel that overcomes the aforementioned
challenges. We chemically polymerized a PEDOT backbone functionalized
with ionic pendant groups to synthesize a water-soluble processable
conjugated polymer without compromising its electronic properties.
Additionally, the side functionalities allowed postfunctionalization
of the polymer to be tailored for desired scaffold requirements. Copolymerizing
of the functional PEDOT with acrylic acid led to a 3D hydrogel with
high water content, a range of mechanical properties that match that
of a number of soft tissues, and electroactivity in physiological
conditions. This is the first report of a conductive network built
from covalently linked conjugated and hydrophilic polymers.</p>
<p>Initial approaches have shown that hydrogels could be made temporarily
conductive either by fabricating hybrid hydrogels in which the CP
is grown in a prefabricated network<sup><xref ref-type="bibr" rid="ref18">18</xref>
,<xref ref-type="bibr" rid="ref19">19</xref>
</sup>
or as single
component nonhybrid conductive hydrogels<sup><xref ref-type="bibr" rid="ref20">20</xref>
,<xref ref-type="bibr" rid="ref21">21</xref>
</sup>
where the CP is the sole polymeric component; however, challenges
remain in their application as components of bioelectronic devices.
Hybrid hydrogels are comprised of CP chains that are physically or
ionically entrapped within the conventional hydrogel matrix which
limit their functionality in physiological conditions. As the hydrogel
swells at physiological pH, physically entrapped CP chains leach out,
which triggers toxicity and causes a drop in electroactivity.<sup><xref ref-type="bibr" rid="ref22">22</xref>
</sup>
Ionically bound CPs are neutralized at pH =
7.4 and eventually leach out of the network, which leads to the same
detrimental drop in properties.<sup><xref ref-type="bibr" rid="ref23">23</xref>
</sup>
Nonhybrid
conductive hydrogels are developed by self-assembly of the polymeric
chains,<sup><xref ref-type="bibr" rid="ref10">10</xref>
,<xref ref-type="bibr" rid="ref24">24</xref>
</sup>
chemical cross-linking,<sup><xref ref-type="bibr" rid="ref20">20</xref>
</sup>
metal ions chelation,<sup><xref ref-type="bibr" rid="ref25">25</xref>
</sup>
freeze-drying
of CP dispersions,<sup><xref ref-type="bibr" rid="ref26">26</xref>
</sup>
or employing a low
molecular weight gelator (LMWG).<sup><xref ref-type="bibr" rid="ref27">27</xref>
,<xref ref-type="bibr" rid="ref28">28</xref>
</sup>
The end product
is a hydrogel network with enhanced electron transport between the
conjugated chains due to the absence of insulating polymers from the
matrix. However, the chemistry currently employed does not allow for
the tuning of properties such as swelling or the mechanical characteristics
of these scaffolds and is not easily amenable for tailoring to accommodate
specific requirements in tissue engineering. In particular, the stability
of hydrogels fabricated via self-assembly or LMWG in physiological
conditions has never been tested. It could be envisioned that ionic
strength will have an effect on the physicochemical properties of
a network and its assembly. A new strategy is presented in this study
to avoid the loss of the CP chains followed by a drop in the material’s
electronic properties.</p>
<p>An ideal precursor for a conductive hydrogel
is a CP with the following
properties: (i) water solubility to enhance swelling capacity, (ii)
functional groups in the side chains that allow chemical cross-linking
to eliminate polymer leaching following swelling in pH 7.4, and (iii)
electrical conductivity in physiological buffers. Here, we report
a functional PEDOT with pendant carboxylic groups (PEDOT-COOH) that
meets all these requirements: water solubility, functionalizable with
demonstrated postmodification capabilities, and preserved electronic
properties upon gelation. PEDOT with pendant carboxylic groups has
been previously reported but via electropolymerization;<sup><xref ref-type="bibr" rid="ref29">29</xref>
</sup>
this limits the scope of application since the
polymer can only be used on electrode surfaces. Reports on chemically
polymerized PEDOT have focused on alkylated, alkoxylated, or alkylsulfonate
derivatives of EDOT.<sup><xref ref-type="bibr" rid="ref30">30</xref>
,<xref ref-type="bibr" rid="ref31">31</xref>
</sup>
However, these substituents do
not offer the potential for the postfunctionalization of the polymer
and thus limit their application in fabricating scaffolds. Furthermore,
the functional carboxylic group ionizes at physiological pH (7.4)
and will allow enhanced swelling of the developed scaffolds. We chose
PEDOT due to its high stability in aqueous solutions<sup><xref ref-type="bibr" rid="ref32">32</xref>
</sup>
and its demonstrated biocompatibility.<sup><xref ref-type="bibr" rid="ref33">33</xref>
</sup>
By synthesizing for the first time a functional PEDOT bearing
carboxylic groups via chemical polymerization, we obtained an electroactive
polymer that could be cross-linked with hydrophilic polymers to form
3D scaffolds with retained electroactivity, high swelling ratios,
and soft mechanical properties.</p>
</sec>
<sec id="sec2"><title>Experimental
Section</title>
<sec id="sec2.1"><title>Materials</title>
<p>Hydroxymethyl EDOT (EDOT-OH) was purchased
from Molekula Ltd., UK. All other chemicals were purchased from Sigma
UK and used without any further purification.</p>
</sec>
<sec id="sec2.2"><title>Synthesis of PEDOT-COOH</title>
<sec id="sec2.2.1"><title>EDOT-COOCH<sub>3</sub>
</title>
<p>EDOT-OH (1.0 g) was dissolved
in anhydrous terahydrofuran (THF) (25 mL) under the flow of N<sub>2</sub>
, and the solution was cooled down by immersing the RB flask
in an ice bath. Potassium iodide (0.19 g) and a NaH suspension (0.278
g) were added, and the solution was left stirring for 30 min. Methyl-3-bromoproprionate
(0.76 mL) was then added dropwise, and the reaction was left stirring
under N<sub>2</sub>
for 48 h. Deionized water (DI-H<sub>2</sub>
O)
was added to quench the reaction, and THF was removed under reduced
pressure. The aqueous mixture was extracted with ethyl acetate, dried
over MgSO<sub>4</sub>
, filtered, and concentrated under reduced pressure.
The crude product was purified by flash chromatography (hexane/ethyl
acetate = 5:1) to give a clear viscous liquid. <sup>1</sup>
H NMR (400
MHz, CDCl<sub>3</sub>
): δ 6.32 (2H, s), 4.26–4.33 (1H,
m), 4.22 (1H, dd, <italic>J</italic>
= 11.6, 2.3 Hz), 4.03 (1H, dd, <italic>J</italic>
= 11.6, 7.5 Hz), 3.79 (2H, t, <italic>J</italic>
= 6.3
Hz), 3.67 (3H, s), 3.62–3.76 (2H, m), 2.62 (2H, t, <italic>J</italic>
= 6.3 Hz) (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S1</ext-link>
).</p>
</sec>
<sec id="sec2.2.2"><title>PEDOT-COOH</title>
<p>The functional PEDOT polymer was synthesized
by chemical oxidation using FeCl<sub>3</sub>
as the oxidant. In a
2-neck RB flask, FeCl<sub>3</sub>
(1.45 g, 8.94 mmol) and anhydrous
chloroform (32 mL) were mixed under the flow of N<sub>2</sub>
. EDOT-COOCH<sub>3</sub>
(0.64 g, 2.48 mmol) was dissolved in anhydrous chloroform
(6 mL) and added dropwise to the oxidant mixture and left stirring
for 24 h at room temperature. The mixture was poured in methanol (∼500
mL) and centrifuged to collect the solid. The precipitate was washed
thoroughly with methanol and then with water until the solvent was
clear. To remove the methyl group on the side chain, the polymer was
treated with 2 M NaOH (50 mL) for 1 day at room temperature and then
filtered to remove the insoluble parts. The filtrate was purple in
color and treated with 10% HCl to precipitate the polymer. The polymer
was washed with water and dried under vacuum to obtain a black solid
(∼100 mg).</p>
</sec>
</sec>
<sec id="sec2.3"><title>Characterization of PEDOT-COOH</title>
<sec id="sec2.3.1"><title>Solid State
NMR</title>
<p>The chemical structure of PEDOT-COOH
was confirmed using a Bruker Avance 111 solid state NMR spectrometer
operating at 75 MHz for <sup>13</sup>
C and 299.75 for <sup>1</sup>
H and fitted with a 4 mm CPMAS probe. Sample (∼60 mg) was
packed into a 4 mm zirconia oxide rotor. Spectra were acquired with
MAS of 12 kHz, using a spin echo sequence allowing for direct <sup>13</sup>
C detection with high power <sup>1</sup>
H decoupling with
spinal 64 sequence at 62 kHz. The relaxation delay was set to 20 s,
and total instrument time was ∼13 h. Cross-polarization failed
to give any signal.</p>
</sec>
<sec id="sec2.3.2"><title><sup>1</sup>
H NMR</title>
<p>PEDOT-COOH (4.9
mg) was dissolved
in DMSO-<italic>d</italic>
<sub>6</sub>
(770.93 mg), and its NMR spectroscopy
was recorded using a Bruker Avance 111, HD 600 with 5 mm TCI cryoprobe.
NMR spectra were processed using the Bruker TOPSPIN 3.0 software.</p>
</sec>
<sec id="sec2.3.3"><title>Gel Permeation Chromatography (GPC)</title>
<p>GPC was performed
using phosphate buffered saline (PBS, 0.1 M) (flow rate: 0.5 mL min<sup>–1</sup>
). A Shimadzu modular system was employed comprising
a DGU-20A3 solvent degasser, an LC-20AT pump, a CTO-20A column oven
operated at 35 °C, and a SPD-M20A diode array UV–vis detector
(200–800 nm). The system was equipped with an Ultrahydrogel
250 column (6 μm, 7.8 × 300 mm) (Waters, WAT01152). Calibration
was achieved using sodium poly(styrenesulfonate) standards (Polymer
Laboratories LTD, UK) ranging from 1400 to 32 000 g mol<sup>–1</sup>
.</p>
</sec>
<sec id="sec2.3.4"><title>Chemical Doping</title>
<p>Drop-casted films
of PEDOT-COOH were
chemically doped by treating the surface with 0.1 M HClO<sub>4</sub>
aqueous solution for 24 h. Excess dopant was wiped gently off the
surface, and the films were rinsed for 30 s with DI-H<sub>2</sub>
O,
dried with N<sub>2</sub>
, and stored in the dark until use.</p>
</sec>
<sec id="sec2.3.5"><title>UV–vis
Spectroscopy</title>
<p>Absorbance spectra were
recorded using a PerkinElmer Lambda 25 UV–vis spectrophotometer.
The spectra of PEDOT-COOH dissolved in water, 1 M NaOH, and dimethyl
sulfoxide (DMSO) as well as that of drop-casted films (doped and undoped)
were recorded. The optical band gap, <italic>E</italic>
<sub>g,opt</sub>
, was estimated from the UV–vis spectra of undoped PEDOT-COOH
film. The linear portion of the curve was extrapolated to the wavelength
axis, and the intercept was determined to be the absorption edge wavelength,
λ<sub>ab</sub>
. <italic>E</italic>
<sub>g,opt</sub>
was calculated
as follows:<sup><xref ref-type="bibr" rid="ref34">34</xref>
,<xref ref-type="bibr" rid="ref35">35</xref>
</sup>
<disp-formula id="ueq1"><graphic xlink:href="cm-2016-01298t_m001" position="anchor"></graphic>
</disp-formula>
where <italic>h</italic>
is the Planck constant
and <italic>c</italic>
is the speed of light.</p>
</sec>
<sec id="sec2.3.6"><title>Spectroelectrochemistry</title>
<p>In situ spectroelectrochemical
measurements were conducted on undoped PEDOT-COOH films prepared by
drop casting on ITO slides (1 × 4 cm). The electrolyte solution
was 0.1 M tetrabutylammonium tetrafluoroborate (TBAB) in acetonitrile.
The reference electrode used was a Ag wire with Pt wire as auxiliary.
The applied voltages on the ITO modified electrode were rescaled vs
Ag/AgCl by using ferrocene. The controlled-potential measurements
were carried out with an eDAQ system controlled by EChem software.</p>
</sec>
<sec id="sec2.3.7"><title>Electrochemistry</title>
<p>Cyclic voltammetry (CV) measurements
were recorded using CHI660D Instrument. The counter electrode was
a platinum mesh, and the reference electrode was Ag/AgCl in saturated
KCl aqueous solution (CHI Instruments). The working electrode was
ITO coated glass (Delta Technologies Limited) on which the PEDOT-COOH
polymer was drop casted. Electrochemical measurements were performed
at different scan rates using 0.1 M TBAB in acetonitrile as the electrolyte
solution. The onset of the oxidation potential, <italic>E</italic>
<sub>ox</sub>
, was determined from the CV. The HOMO–LUMO levels
were determined as follows:<sup><xref ref-type="bibr" rid="ref36">36</xref>
</sup>
<disp-formula id="ueq2"><graphic xlink:href="cm-2016-01298t_m002" position="anchor"></graphic>
</disp-formula>
<disp-formula id="ueq3"><graphic xlink:href="cm-2016-01298t_m003" position="anchor"></graphic>
</disp-formula>
</p>
</sec>
</sec>
<sec id="sec2.4"><title>Hydrogel
Fabrication</title>
<sec id="sec2.4.1"><title>Functional PEDOT (f-PEDOT)</title>
<p>To introduce
a double bond
in the side chain of PEDOT-COOH, the polymer was reacted with <italic>N</italic>
-(3-aminopropyl) methacrylamide hydrochloride (APMA). PEDOT-COOH
(0.355 g) was dissolved in DMSO (30 mL) at 60 °C and then cooled
to room temperature. APMA (0.117 g) and <italic>N</italic>
-(3-(dimethylamino)propyl)-<italic>N</italic>
′-ethylcarbodiimide hydrochloride (EDC) (0.249 g)
were added, and the reaction was left to stir for 24 h. To wash out
all the byproducts and unreacted monomer (APMA), the solution was
poured into excess water, which led to the precipitation of a black
solid. The black solid was collected by centrifugation, washed repeatedly
with water, and dried under vacuum to give f-PEDOT in powder form.</p>
</sec>
<sec id="sec2.4.2"><title><sup>1</sup>
H NMR</title>
<p>f-PEDOT (5.0 mg) was dissolved in
DMSO-<italic>d</italic>
<sub>6</sub>
(768.25 mg), and its NMR spectroscopy
was recorded as described above. The degree of substitution of APMA
was quantified using an external reference (trioxane (10.5 mg) in
DMSO-<italic>d</italic>
<sub>6</sub>
(771.65 mg)) and using Topspin
Eretic Software.</p>
</sec>
<sec id="sec2.4.3"><title>Elemental Analysis</title>
<p>Elemental analysis
was performed
at Campbell Microanalytical Laboratory, University of Otago, New Zealand.
Samples were precisely weighed on a Mettler UMT2 microbalance into
lightweight tin capsules and dropped into a combustion tube of the
elemental analyzer (Carlo Erba EA 1108) through which a constant stream
of helium is maintained. Total carbon, hydrogen, nitrogen, and sulfur
were determined for both PEDOT-COONa and f-PEDOT.</p>
</sec>
<sec id="sec2.4.4"><title>f-PEDOT Hydrogel</title>
<p>To fabricate a cross-linked functional
PEDOT hydrogel, f-PEDOT was copolymerized with acrylic acid (AA) in
the presence of poly(ethylene glycol) diacrylate (PEG-DA, average
molecular number (<italic>M</italic>
<sub>n</sub>
) = 700) as a cross-linker
and 2,2′-azobis(2-methyl-proprionitrile) (AIBN) as the initiator.
In a typical procedure, f-PEDOT (5 mg) was dissolved in DMSO (1 mL)
at 60 °C to a final concentration of 0.5 wt % polymer. The solution
was then cooled to room temperature. AA (95.2 μL), PEG-DA (10
μL), and AIBN (2 mg) were added to the polymer solution, and
it was vortexed and left at 60 °C for 24 h. Gelation of the solutions
was confirmed by the test tube inverting method. The vials containing
the mixture were inverted, and gelation was deemed to have occurred
when no flow of liquid was observed. The hydrogels were then removed
from the vials, washed with excess 10% (w/v) HCl for 1 day, and then
soaked in excess DI-H<sub>2</sub>
O for 3 days. The hydrogels were
then freeze-dried and stored until use. Poly(acrylic acid) (PAA) hydrogels
were fabricated according to the same procedure but without adding
f-PEDOT in the solution.</p>
</sec>
</sec>
<sec id="sec2.5"><title>Characterization of the
Physical Properties of f-PEDOT Hydrogel</title>
<sec id="sec2.5.1"><title>Swelling Studies</title>
<p>The dry weights of freeze-dried hydrogels
were recorded (<italic>m</italic>
<sub>d</sub>
) before incubating the
samples in PBS (0.1 M, pH = 7.3, 37 °C) and then leaving them
to swell until equilibrium was reached. At predetermined time points,
the samples were removed and gently blotted, and their swollen weight
(<italic>m</italic>
<sub>s</sub>
) was recorded. The percentage-swelling
ratio was calculated according to the following equation:<disp-formula id="ueq4"><graphic xlink:href="cm-2016-01298t_m004" position="anchor"></graphic>
</disp-formula>
A total of 9 specimens were measured
at each
time point.</p>
</sec>
<sec id="sec2.5.2"><title>Mechanical Properties</title>
<p>The compression
modulus of cylindrical
hydrogels was measured at room temperature using a Bose Instrument
equipped with a 3 N load cell. Samples were removed from the swelling
media and blotted dry to get rid of excess water. The thickness and
radius (<italic>r</italic>
) of each sample was measured before running
the test (listed in <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Table S1</ext-link>
). The samples
were placed between parallel plates and compressed at 0.1%/s strain
rate. The stress was calculated according to<disp-formula id="ueq5"><graphic xlink:href="cm-2016-01298t_m005" position="anchor"></graphic>
</disp-formula>
where <italic>r</italic>
is the initial unloaded
radius. The strain under compression was defined as the change in
the thickness relative to the thickness of the freestanding specimen.
The compression modulus was calculated from the slope of the linear
region of the stress–strain plot at less than 15% deformation.
Results were reported for hydrogels in two different states: swollen
in PBS (<italic>n</italic>
= 5) and HClO<sub>4</sub>
-doped hydrogels
(<italic>n</italic>
= 4).</p>
</sec>
</sec>
<sec id="sec2.6"><title>Characterization of the
Electronic Properties of f-PEDOT Hydrogel</title>
<sec id="sec2.6.1"><title>Chemical Doping of f-PEDOT
Hydrogel</title>
<p>Hydrogels were
soaked in 0.1 M HClO<sub>4</sub>
aqueous solution for 24 h. This was
followed by rinsing with water and freeze-drying the samples.</p>
</sec>
<sec id="sec2.6.2"><title>Electrochemistry</title>
<p>Freeze-dried hydrogels (undoped and
doped) were anchored on gold mylar surfaces and soaked in PBS for
10–15 min to allow for water uptake. CVs were then recorded
as described above but using PBS (pH = 7.4) as the electrolyte.</p>
</sec>
<sec id="sec2.6.3"><title>Impedance</title>
<p>The electrochemical impedance (EIS) spectra
of PAA (control) and f-PEDOT hydrogels were measured using Solartron
SI 1287 electrochemical interface coupled with an SI 1260 frequency
response analyzer (Solectron Analytical, Hampshire, England) from
10 kHz to 1 Hz with an applied AC potential of 10 mV versus the reference
electrode potential. Before recording the measurements, hydrogels
were anchored on gold mylar and incubated in PBS for 24 h to ensure
swelling to equilibrium. Ag/AgCl and Pt electrodes were used as the
reference and counter electrodes, respectively. The applied DC voltage
was 290 mV, and the electrolyte solution was PBS (0.1 M).</p>
</sec>
</sec>
<sec id="sec2.7"><title><italic>In Vitro</italic>
Cell Studies</title>
<sec id="sec2.7.1"><title>Cell Lines and Reagents</title>
<p>All reagents were purchased
from Life Technologies (UK) unless otherwise stated. Mouse C3H muscle
myoblast line (C2C12) was purchased from ATCC. Horse serum was purchased
from Sigma. Cells were maintained in Dulbecco’s modified Eagle’s
medium (DMEM) supplemented with 20% (v/v) fetal bovine serum (FBS)
and antibiotics (100 units/mL penicillin and 100 μg/mL streptomycin),
under standard mammalian cell culture conditions. The high concentration
of FBS provides a rich source of mitogenic growth factors required
for optimal cell growth and proliferation while the addition of antibiotics
prevents the growth of potential bacterial contaminants. Media was
replaced every other day.</p>
</sec>
<sec id="sec2.7.2"><title>Cell Culture</title>
<p>Hydrogels were transferred
into 24 well
plates and sterilized by cell culture-grade UV light irradiation for
1 h. The samples were then soaked in DI-H<sub>2</sub>
O overnight prior
to cell seeding in order to wash excess acid from the doped samples.
The next day, to meet the required environment for cell culture, water
was removed from the wells and replaced with media for 1 h which was
then removed before seeding the cells. C2C12 cells were detached from
the culture plates using trypsin, followed by centrifugation (6000<italic>g</italic>
, 5 min). The cell pellet was resuspended in fresh media.
Cells (1.5 × 10<sup>6</sup>
cells in 30 μL) were dispensed
on the surface of the hydrogels and left for 1 h to allow for adhesion.
Adherence of C2C12s to the surface is necessary for the cells to remain
viable and for all cell function (cell division, migration, and maturation).
The wells were then filled with growth media and allowed to proliferate
for 3 days. Cells were then washed to remove traces of the growth
medium. Although the greatest care was taken, some cells could have
been dislodged during this process. The cells attached to the hydrogels
were then placed in a differentiating media (DMEM with 2% (v/v) horse
serum, 100 units/mL penicillin, and 100 μg/mL streptomycin antibiotics)
and incubated for 5 days. Horse serum was included in the differentiation
medium to provide a minimal level of nutrients which are needed to
keep the cells healthy and viable. At various time points, differentiation
media was removed and the cells/hydrogels were washed in PBS before
being submerged in freshly prepared fixation buffer (4% (v/v) paraformaldehyde
in PBS) for 10 min at room temperature. Excess fixative was washed
away with PBS.</p>
</sec>
<sec id="sec2.7.3"><title>Immunostaining</title>
<p>Fixed hydrogels were
cut into 250 μm
cross-sectional and longitudinal slices using a high precision vibrating
microtome (7000 smz, Campden Instruments Ltd., UK). The slices were
blocked in 5% (v/v) FBS in PBS for 2 h and then incubated overnight
at 4 °C with primary antibodies that specifically bind to the
proteins Ki67 and desmin (Abcam; ab8470 and ab15580) or myosin heavy
chain IIb (MHC IIb, clone MF20; RnD systems). Unbound primary antibodies
were removed by 3 × 20 min washes in PBS. To visualize the bound
antibodies, the cells were incubated in secondary antibodies labeled
with fluorophores (goat antimouse Alexa 488 and goat antirabbit Alexa
488; Invitrogen). For some experiments, cells/hydrogels were also
incubated in Alexa Fluor 594-phalloidin (Invitrogen). Phalloidin is
a peptide that binds to actin in cells and allows visualization of
cell shape. DAPI was used to label nuclei. Confocal microscopy was
performed using a Zeiss LSM-780 inverted microscope.</p>
</sec>
</sec>
</sec>
<sec id="sec3"><title>Results
and Discussion</title>
<p>We achieved the synthesis of PEDOT-COOH (<xref rid="sch1" ref-type="scheme">Scheme <xref rid="sch1" ref-type="scheme">1</xref>
</xref>
A) by oxidation polymerization
of EDOT-COOCH<sub>3</sub>
(<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S1</ext-link>
) followed
by deprotection
in NaOH; this yielded a polymer with carboxylic groups in the backbone
(<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S2A</ext-link>
). The chemical structure of
the polymer was also confirmed by solution NMR (broadened peaks, <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S2B</ext-link>
) and elemental analysis (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Table S2</ext-link>
). The resultant polymer had a weight-average
molecular weight (<italic>M</italic>
<sub>w</sub>
) of 10 102
g·mole <sup>–1</sup>
and a polydispersity of 2.49 as determined
by GPC. The polymer was soluble in DMSO (1 wt %), water (∼0.6
wt %), and basic aqueous pH solutions (10 wt % at pH 12). This conferred
solubility provides an advantage over the more commonly used form
of PEDOT, which is a dispersion in water stabilized with high concentrations
of poly(styrenesulfonate) (PSS). <xref rid="fig1" ref-type="fig">Figures <xref rid="fig1" ref-type="fig">1</xref>
</xref>
A and <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">S3</ext-link>
show
the absorption spectra of PEDOT-COOH film and solutions, respectively.
A broad absorption band, λ<sub>max</sub>
≈ 519 nm for
the films and 480 nm for solutions, was detected corresponding to
the π–π* transition in the conjugated backbone.<sup><xref ref-type="bibr" rid="ref32">32</xref>
</sup>
The optical band gap (<italic>E</italic>
<sub>g,opt</sub>
) determined from the film spectra was 1.70 ± 0.09
eV. This value is in the range (1.5–2.0 eV) of other chemically
synthesized derivatives of PEDOT,<sup><xref ref-type="bibr" rid="ref32">32</xref>
,<xref ref-type="bibr" rid="ref34">34</xref>
,<xref ref-type="bibr" rid="ref37">37</xref>
</sup>
which indicated that EDOT-COOCH<sub>3</sub>
polymerization
proceeded efficiently to produce a functional PEDOT polymer with sufficient
conjugation length.</p>
<fig id="sch1" position="float"><label>Scheme 1</label>
<caption><title>(A) Synthesis of PEDOT-COOH Polymer; (B) Fabrication
of f-PEDOT Hydrogel</title>
</caption>
<graphic xlink:href="cm-2016-01298t_0006" id="gr1" position="float"></graphic>
</fig>
<fig id="fig1" position="float"><label>Figure 1</label>
<caption><p>Monitoring the electronic properties of the PEDOT-COOH polymer.
(A) Spectroelectrochemistry of a PEDOT-COOH film drop-casted on ITO-coated
glass as a function of applied potential between −0.54 and
0.86 V. (B) UV–vis absorption spectra of reduced (−)
and HClO<sub>4</sub>
doped (- - -) PEDOT-COOH films. (C) Cyclic voltammogram
(25 mV·s<sup>–1</sup>
) of PEDOT-COOH film drop-casted
on ITO-coated glass in TBAB acetonitrile solution (0.1 M).</p>
</caption>
<graphic xlink:href="cm-2016-01298t_0002" id="gr2" position="float"></graphic>
</fig>
<p>We conducted in situ spectroelectrochemistry to
elucidate the electronic
properties of the modified PEDOT (<xref rid="fig1" ref-type="fig">Figure <xref rid="fig1" ref-type="fig">1</xref>
</xref>
A). In the absence of a bias, the film exhibited
a broad peak at ∼513 nm, which suggested that the film was
in the anticipated reduced state following treatment in NaOH. As the
potential exceeded 0 V, the intensity of the peak decreased along
with the appearance of a new absorption feature in the near-infrared
region (>800 nm), which is representative of polaronic states.
This
suggested a substantial change in the oxidation state of the PEDOT-COOH
film from reduced to oxidized as the positive bias was applied. Chemical
treatment of the films with HClO<sub>4</sub>
caused a similar switch
between the reduced (undoped) and oxidized form (doped) (<xref rid="fig1" ref-type="fig">Figure <xref rid="fig1" ref-type="fig">1</xref>
</xref>
B). Hence, it could
be inferred that the PEDOT-COOH is a conjugated polymer with intrinsic
electroactivity.</p>
<p>To further confirm the conjugated nature of
the polymer, we examined
the electrochemical behavior of the modified PEDOT in tetrabutylammonium
tetrafluoroborate (TBAB) electrolyte solution (<xref rid="fig1" ref-type="fig">Figure <xref rid="fig1" ref-type="fig">1</xref>
</xref>
C). The film exhibited good redox activity
with a broad anodic (0.314–0.735 V) and a broad cathodic peak
(0.32–0.19 V). This indicated that the electron transfer ability
of the chemically polymerized PEDOT was not hindered by the carboxylic
group in the side chain. A linear relation was also established between
the peak current and the potential scan rate (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S4</ext-link>
), which denoted that the electron transfer process
was not diffusion limited<sup><xref ref-type="bibr" rid="ref38">38</xref>
,<xref ref-type="bibr" rid="ref39">39</xref>
</sup>
and that the PEDOT
film was in intimate contact with the ITO electrode. From the experimental
results of cyclic voltammetry (CV) and UV spectrophotometry, the calculated
values of the HOMO and LUMO of PEDOT-COOH were −5.28 and −3.51
eV, respectively, which was comparable to other reported values for
PEDOT polymers.<sup><xref ref-type="bibr" rid="ref34">34</xref>
,<xref ref-type="bibr" rid="ref37">37</xref>
</sup>
</p>
<p>Introducing a functional
group in the side chain of PEDOT enabled
postfunctionalization of the polymer. We reacted PEDOT-COOH with <italic>N</italic>
-(3-aminopropyl) methacrylamide hydrochloride (APMA) to
introduce a double bond in the chain (f-PEDOT) (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figures S5 and S6A</ext-link>
). Using an external reference (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S6B</ext-link>
), the degree of substitution was determined
to be ∼20 wt %. This was confirmed by elemental analysis that
showed the presence of nitrogen in f-PEDOT as opposed to PEDOT-COOH
(<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Table S2</ext-link>
) and a degree of substitution
approximated at ∼16 wt %. f-PEDOT was then polymerized for
24 h with acrylic acid (AA)<sup><xref ref-type="bibr" rid="ref40">40</xref>
</sup>
and poly(ethylene
glycol) diacrylate (PEG-DA) to fabricate a 3D cross-linked gel comprised
of poly(acrylic acid) (PAA) chains covalently linked to f-PEDOT via
the PEG-DA (<xref rid="sch1" ref-type="scheme">Scheme <xref rid="sch1" ref-type="scheme">1</xref>
</xref>
B). Each of the three components works synergistically to produce
a conductive 3D hydrogel, namely: PAA is a polyelectrolyte that ionizes
in physiological pH and causes water uptake; PEG-DA is a cross-linker
that covalently binds the polymeric chains to produce the 3D structure;
PEDOT is a conjugated polymer that introduces redox and electronic
activity into the scaffold.</p>
<p>The gel was removed from the glass
vial and sectioned into specimens
5 mm in thickness. The gel is dark in color (<xref rid="sch1" ref-type="scheme">Scheme <xref rid="sch1" ref-type="scheme">1</xref>
</xref>
B). While this could be a limiting factor
for external bioapplications, many of the electroresponsive tissues
that could benefit from the conductive gel are internal organs such
as the heart, spinal cord, or the brain. The specimens were washed
repeatedly with 10% HCl, which ensured the exchange of DMSO with acidic
water without causing uncontrolled swelling of the gels if soaked
immediately in water. The specimens were then transferred into excess
DI-H<sub>2</sub>
O and left to soak for 48 h. Of significance here
is that the chemically produced PEDOT can be functionalized with a
plethora of compounds other than APMA or copolymerized with other
monomers or polymers bearing double bonds.</p>
<p>Considering the hydrophobic
nature of the f-PEDOT backbone due
to the presence of aromatic rings, it was important to investigate
whether the CP in the network hindered the swelling behavior of the
hydrogel. Freeze-dried specimens were incubated in PBS (pH = 7.4 at
37 °C) and weighed at different times. Hydrogels were found to
exhibit a remarkable water uptake after 48 h (∼5000%), which
was comparable to the swelling ratio of other PAA copolymer hydrogels
(<xref rid="fig2" ref-type="fig">Figure <xref rid="fig2" ref-type="fig">2</xref>
</xref>
A).<sup><xref ref-type="bibr" rid="ref41">41</xref>
</sup>
The swelling of the hydrogels was due to the
ionization at pH = 7.4 of the pendant carboxylic groups present on
both polymers (PAA and f-PEDOT). As the proton of the carboxylic groups
dissociates in pH = 7.4, electrostatic repulsion between the polymer
chains caused the network to uptake water. Compared to previously
reported conductive hydrogels,<sup><xref ref-type="bibr" rid="ref12">12</xref>
,<xref ref-type="bibr" rid="ref18">18</xref>
,<xref ref-type="bibr" rid="ref22">22</xref>
</sup>
our f-PEDOT hydrogel displayed significantly higher ratio of swelling,
which is an attractive property for applications in tissue engineering
and drug delivery. With their high water content, these conductive
hydrogels present tissue engineering advantages for soft tissue. Strong
water uptake promises for efficient mass transfer, which is advantageous
for applications of the hydrogel in cell proliferation and tissue
formation.</p>
<fig id="fig2" position="float"><label>Figure 2</label>
<caption><p>Monitoring the physical properties of the f-PEDOT hydrogel. (A)
Percentage swelling ratio of undoped hydrogels. (B) Young’s
modulus of hydrogel networks swollen in different media (<italic>p</italic>
< 0.005).</p>
</caption>
<graphic xlink:href="cm-2016-01298t_0003" id="gr3" position="float"></graphic>
</fig>
<p>It is well established
that the stiffness of any scaffold dictates
the cell–biomaterial interaction.<sup><xref ref-type="bibr" rid="ref42">42</xref>
</sup>
Since the conductive hydrogel is designed to function as a scaffold
for cell seeding and attachment, we characterized its mechanical properties.
Additionally, the redox state of the polymer (doped versus undoped)
might alter the mechanical properties of the network; hence, we measured
the compressive moduli of both doped and undoped scaffolds (<xref rid="fig2" ref-type="fig">Figure <xref rid="fig2" ref-type="fig">2</xref>
</xref>
B). The Young modulus
of PBS treated samples was 8.2 ± 3.1 kPa, respectively. In contrast,
doped hydrogels displayed an increased stiffness (45.14 ± 18.78
kPa, <italic>p</italic>
< 0.005, Tukey’s multiple comparison
test, one-way ANOVA). Monitoring the swelling of the samples in the
dopant solution (0.1 M HClO<sub>4</sub>
) revealed minimal water uptake
compared to those in PBS (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S7</ext-link>
). In
a low pH media, the carboxylic groups are protonated and the polymeric
chains come into closer vicinity, which could lead to secondary bonds
between the aromatic rings, and in turn increases the mechanical strength
of the network.</p>
<p>Having established that the f-PEDOT hydrogel
displayed desirable
physical characteristics of a network applicable to tissue engineering
(high swelling ratios and mechanical integrity), we characterized
its electronic properties to examine whether f-PEDOT retained its
electroactivity in the presence of the insulators PAA and PEG-DA.
Redox activity of the scaffold is important to show that the material
being designed is capable of providing an electrical stimulus, which
will ultimately allow for direct stimulation of cells and the transduction
of biological signals to be promising. <xref rid="fig3" ref-type="fig">Figure <xref rid="fig3" ref-type="fig">3</xref>
</xref>
A shows the electrochemistry of the f-PEDOT
hydrogel in PBS as an electrolyte. The CVs exhibited characteristic
features comparable to those of the PEDOT-COOH polymer (<xref rid="fig1" ref-type="fig">Figure <xref rid="fig1" ref-type="fig">1</xref>
</xref>
C); broad anodic and reduction
peaks at ∼0.48 and ∼0.35 V, respectively, with a half-wave
potential, <italic>E</italic>
<sub>1/2</sub>
, of 0.415 V, which indicated
that a clear effective charge transport is occurring in the f-PEDOT
hydrogel despite the swollen state and the presence of insulating
polymers (PAA and PEG) in the network. Furthermore, hydrogels subject
to repeated cycles exhibited a stable electrochemical response (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S8</ext-link>
).</p>
<fig id="fig3" position="float"><label>Figure 3</label>
<caption><p>Cyclic voltammograms of (A) undoped and
(B) doped hydrogels in
0.1 M PBS conducted at different potential scan rates.</p>
</caption>
<graphic xlink:href="cm-2016-01298t_0004" id="gr4" position="float"></graphic>
</fig>
<p>After doping the hydrogels with 0.1 M HClO<sub>4</sub>
, we observed
a shift in the <italic>E</italic>
<sub>1/2</sub>
to lower potentials
(<italic>E</italic>
<sub>1/2=</sub>
0.29 V; anodic peak at 0.31 V and
cathodic peak at 0.27 V) (<xref rid="fig3" ref-type="fig">Figure <xref rid="fig3" ref-type="fig">3</xref>
</xref>
B). This indicated that the oxidation of the doped
network required a lower potential compared to the undoped network.
The CVs of the undoped system also showed a quasi-reversible process
with oxidation and reduction peak separation increasing with potential
scan rate. Following doping, the CVs became more reversible (<xref rid="fig3" ref-type="fig">Figure <xref rid="fig3" ref-type="fig">3</xref>
</xref>
B), which indicated
a faster charge transport kinetics due to the higher electrical conductivity
in the doped system.</p>
<p>We could also infer from the linear relation
between the potential
scan rate and anodic peak current that both the doped and undoped
hydrogels were in good contact with the electrode surface (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S9</ext-link>
). In contrast, PAA hydrogels displayed
no redox activity as shown by the absence of oxidation/reduction waves
in their cyclic voltammogram (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S10</ext-link>
). The redox activity of the doped hydrogels was further confirmed
by electrochemical impedance spectroscopy (EIS) conducted at 290 mV
(<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S11</ext-link>
). Unlike the Nyquist plot of
the PAA system, the Nyquist plot of the doped hydrogel showed a quasi-semicircular
arc in the high frequency regime (inset <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S11</ext-link>
). This implies a redox activity as opposed to a capacitive
behavior of the nonredox active PAA system. This was further evidence
that the modified PEDOT scaffold retained its electroactive properties
in aqueous electrolytes and despite the attachment of functional groups
to its side chains.</p>
<p>Envisioned applications of the PEDOT-COOH
as a component of bioelectronic
devices will require the polymer to be in contact with electroresponsive
tissue. Additionally, the conductive and electroactive nature of our
developed f-PEDOT hydrogel in the swollen state, along with its favorable
swelling ratio and mechanical integrity, make it suitable as a 3D-scaffold
for the proliferation and differentiation of electro-responsive cells.
C2C12 cells are a mouse myoblast cell line commonly used as an <italic>in vitro</italic>
model to study muscle differentiation. We seeded
C2C12 cells on both undoped and doped scaffolds and assessed qualitatively
for adhesion and viability at day 3. As shown in <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S12</ext-link>
, the f-PEDOT hydrogels promoted cell adhesion without
the need to precoat the scaffold with any cell-adhesion protein (such
as fibronectin or laminin). Significantly, other conjugated based
systems normally require modification of their surfaces with adhesive
molecules to enhance their cytocompatibility and cell attachment.
Of particular interest was the migration of the cells from the surface
into the 3D highly swollen and porous structure of the hydrogels (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S13</ext-link>
). We found that cells penetrated to
a depth of ∼2 mm, which confirmed the cytocompatibility of
the conductive hydrogel (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">Figure S13E–G</ext-link>
). The structural composition of the C2C12 cells was confirmed by
phalloidin stain for actin (<xref rid="fig4" ref-type="fig">Figure <xref rid="fig4" ref-type="fig">4</xref>
</xref>
A,B). Actin is a critical component in many structural
and functional processes in the cell. The phalloidin staining confirmed
that the structural network remained undamaged on both doped and undoped
hydrogels. Proliferation of C2C12 cells was confirmed by Ki67 staining
on both undoped and doped hydrogels (<xref rid="fig4" ref-type="fig">Figure <xref rid="fig4" ref-type="fig">4</xref>
</xref>
A,B). The Ki67 protein is present in the
cell nucleus during all active phases of the cell cycle (G1, S, G2,
and mitosis) but is absent from resting cells (G0). Detection of the
Ki67 protein by immunostaining indicates that the cells are proliferating;
thus, the hydrogels support muscle cell expansion. When C2C12 myoblasts,
immature muscle cells, are grown to a high density, they can begin
to differentiate. To facilitate this process, the cells are placed
in low serum conditions as the growth factor withdrawal initiates
a differentiation program. In this multistep process, the myoblasts
stop proliferating, elongate, and align next to each other before
they are then in a position to fuse together to form multinucleated
tubes capable of contraction. Cells grown in the hydrogel were observed
to align at day 3 (<xref rid="fig4" ref-type="fig">Figures <xref rid="fig4" ref-type="fig">4</xref>
</xref>
C and <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">S12 and S14</ext-link>
), and multinucleated
tubes were present by day 7 (<xref rid="fig4" ref-type="fig">Figure <xref rid="fig4" ref-type="fig">4</xref>
</xref>
C) indicating that cells were able to differentiate
in the hydrogels. In addition to morphological changes, maturing muscle
myoblasts such as C2C12s begin to produce proteins required for their
contractile function, such as MHC IIb (<xref rid="fig4" ref-type="fig">Figure <xref rid="fig4" ref-type="fig">4</xref>
</xref>
C). MHC IIb is a motor protein that generates
force to drive muscle contraction and is an essential component of
functional muscle. Expression of this protein is therefore used as
a marker of C2C12 maturation. The presence of MHC IIb in cells grown
in both doped and undoped hydrogels shows that both forms of the hydrogel
are conducive to the maturation of muscle cells.</p>
<fig id="fig4" position="float"><label>Figure 4</label>
<caption><p>C2C12 cultured in f-PEDOT
hydrogel; proliferation of cells in undoped
(A) and doped hydrogels (B) at day 3. Proliferation is indicated by
positive nuclear Ki67 staining (green), while phalloidin staining
for actin (red) allows visualization of the cell shape. DAPI stain
labels the DNA in nuclei (blue). C) Staining for the mature muscle
marker myosin heavy chain IIb (MHC IIb) (green) and DAPI (blue) in
undoped and doped hydrogel at day 3 and day 7. The presence of MHCIIb
shows that the C2C12s, which are immature muscle cells and normally
have low expression of MHCIIb, are becoming mature muscle cells when
seeded on the hydrogel. While the C2C12s exist as single cells at
day 3, multicellular tubes are observed by day 7 showing increased
maturation with continued culture time.</p>
</caption>
<graphic xlink:href="cm-2016-01298t_0005" id="gr5" position="float"></graphic>
</fig>
<p>In summary, we found that C2C12 cells grown in both the doped
and
undoped samples formed myotube structures and expressed MHC IIb (<xref rid="fig4" ref-type="fig">Figure <xref rid="fig4" ref-type="fig">4</xref>
</xref>
C) indicating that
they were differentiating. Coupled with their expression of Ki67 (<xref rid="fig4" ref-type="fig">Figure <xref rid="fig4" ref-type="fig">4</xref>
</xref>
A,B), this showed
that our hydrogels were capable of sustaining the differentiation
of C2C12 cells in addition to their proliferating precursors. This <italic>in vitro</italic>
study was conducted as evidence of biocompatibility
of the newly fabricated PEDOT based hydrogels. Future studies will
investigate the mechanistic insight into the role of the hydrogel
on cellular differentiation.</p>
</sec>
<sec id="sec4"><title>Conclusion</title>
<p>In this study, we successfully
produced an electroactive hydrogel
network composed of PEDOT covalently bound to a hydrophilic polymer.
This led to the formation of a scaffold combining both the appropriate
physical properties of a hydrogel and the electronic characteristics
of a conjugated polymer. We achieved this by synthesizing a processable
PEDOT with functional groups tethered on the side chains that could
be further modified to fabricate a covalently linked polymeric network.
The PEDOT-COOH was shown to be electroactive as both a pristine polymer
and a component of the hydrogel. Finally, we demonstrated the suitability
of these scaffolds as hydrated 3D structures for cell adhesion, proliferation,
and differentiation. The next step will be to employ these electroactive
hydrogels in bioelectronics devices and test their capacity to either
electrically stimulate electroresponsive cells or probe the bioelectric
signals. Covalently linking PEDOT with hydrophilic polymers to produce
scaffolds of tailored properties represents a major advance in tissue
engineering that paves the way for the smart design of conductive
functional scaffolds.</p>
</sec>
</body>
<back><notes id="notes-1" notes-type="si"><title>Supporting Information Available</title>
<p>The Supporting Information
is available free of charge on the <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org">ACS Publications website</ext-link>
at DOI: <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/abs/10.1021/acs.chemmater.6b01298">10.1021/acs.chemmater.6b01298</ext-link>
.<list id="silist" list-type="simple"><list-item><p>Tables of hydrogel
dimensions and elemental analysis; <sup>1</sup>
H-NMR data, solid state
CP-MAS <sup>13</sup>
C data, UV-vis
absorption spectra, redox peak currents, percentage swelling ratios,
cyclic voltammograms, Nyquist plot, images of C2C12 cultures and f-PEDOT
hydrogel (<ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/doi/suppl/10.1021/acs.chemmater.6b01298/suppl_file/cm6b01298_si_001.pdf">PDF</ext-link>
)</p>
</list-item>
</list>
</p>
</notes>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data" id="sifile1"><media xlink:href="cm6b01298_si_001.pdf"><caption><p>cm6b01298_si_001.pdf</p>
</caption>
</media>
</supplementary-material>
</sec>
<notes id="notes-2"><title>Author Contributions</title>
<p><sup>¶</sup>
D.M. and A.A.-S. contributed equally.</p>
</notes>
<notes id="notes-3" notes-type="funding-statement"><p>D.M.
was supported
by Marie Curie actions FP7 through the Intra-European Marie Curie
Fellowship “MultiFun CP” under grant agreement no. 328897.
M.M.S. acknowledges the support from the ERC Seventh Framework Programme
Consolidator grant “Naturale CG” under grant agreement
no. 616417 and a Wellcome Trust Senior Investigator Award (098411/Z/12/Z)
for funding. M.M.M. would like to thank the Public Service Department
of Malaysia for the PhD scholarship via King of Malaysia scheme and
University Teknologi MARA (UiTM). J.T. acknowledges the British Heart
Foundation grant RM/13/1/30157.</p>
</notes>
<notes id="notes-4" notes-type="conflict-of-interest"><p>The authors
declare no competing financial interest.</p>
</notes>
<ack><title>Acknowledgments</title>
<p>The authors would
like to acknowledge Dr. Douglas Lawes and
Dr. James Hook of the NMR Facility within the Mark Wainwright Analytical
Centre at the University of New South Wales for NMR support. Also,
we would like to thank Dr. Patricia Y. Hayes from the Australian National
Fabrication Facility (ANFF) and Dr. Pawel Wagner from the ARC Centre
of Excellence for Electromaterials Science (ACES) for conducting the
GPC experiment.</p>
</ack>
<glossary id="dl1"><def-list><title>Abbreviations</title>
<def-item><term>AA</term>
<def><p>acrylic acid</p>
</def>
</def-item>
<def-item><term>AIBN</term>
<def><p>2,2′-azobis(2-methyl-proprionitrile)</p>
</def>
</def-item>
<def-item><term>APMA</term>
<def><p><italic>N</italic>
-(3-aminopropyl) methacrylamide hydrochloride</p>
</def>
</def-item>
<def-item><term>CP</term>
<def><p>conducting polymer</p>
</def>
</def-item>
<def-item><term>DMEM</term>
<def><p>Dulbecco’s modified Eagle’s
medium</p>
</def>
</def-item>
<def-item><term>EDC</term>
<def><p><italic>N</italic>
-(3-(dimethylamino)propyl)-<italic>N</italic>
′-ethylcarbodiimide
hydrochloride</p>
</def>
</def-item>
<def-item><term>HOMO</term>
<def><p>highest occupied molecular orbital</p>
</def>
</def-item>
<def-item><term>LUMO</term>
<def><p>lowest unoccupied molecular orbital</p>
</def>
</def-item>
<def-item><term>PAA</term>
<def><p>poly(acrylic acid)</p>
</def>
</def-item>
<def-item><term>PEDOT</term>
<def><p>poly(ethylenedioxy
thiophene)</p>
</def>
</def-item>
<def-item><term>PEG-DA</term>
<def><p>poly(ethylene glycol) diacrylate</p>
</def>
</def-item>
<def-item><term>TBAB</term>
<def><p>tetrabutylammonium borate</p>
</def>
</def-item>
</def-list>
</glossary>
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<given-names>M. Y.</given-names>
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