Photophysical Properties and Efficient, Stable, Electrogenerated Chemiluminescence of Donor-Acceptor Molecules Exhibiting Thermal Spin Upconversion.
Identifieur interne : 000012 ( PubMed/Corpus ); précédent : 000011; suivant : 000013Photophysical Properties and Efficient, Stable, Electrogenerated Chemiluminescence of Donor-Acceptor Molecules Exhibiting Thermal Spin Upconversion.
Auteurs : Ryoichi Ishimatsu ; Tomohiko Edura ; Chihaya Adachi ; Koji Nakano ; Toshihiko ImatoSource :
- Chemistry (Weinheim an der Bergstrasse, Germany) ; 2016.
Abstract
The photophysical properties and electrogenerated chemiluminescence (ECL) of three donor-acceptor molecules composed of dicyanobenzene and methyl-, tert-butyl-, and phenyl-substituted carbazolyl groups, 1,2,3,5-tetrakis(3,6-disubstituted-carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN-Me, 4CzIPN-tBu, and 4CzIPN-Ph, respectively) are described. These molecules show delayed fluorescence as a result of thermal spin upconversion from the lowest triplet state to the lowest singlet state at room temperature. The three molecules showed yellow to yellowish-red ECL. Remarkably, the ECL efficiencies of 4CzIPN-tBu in dichloromethane reached almost 40 %. Moreover, stable ECL was emitted from 4CzIPN-tBu and 4CzIPN-Ph. In case of 4CzIPN-Me, the ECL intensity decreased during voltage cycles because of polymerization. Quantum chemical calculations revealed that polymerization was inhibited by the steric hindrance of the bulky tert-butyl and phenyl groups on the carbazolyl moieties and lowered the spin density on the carbazolyl groups through electron conjugation for 4CzIPN-Ph.
DOI: 10.1002/chem.201600077
PubMed: 26916843
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Photophysical Properties and Efficient, Stable, Electrogenerated Chemiluminescence of Donor-Acceptor Molecules Exhibiting Thermal Spin Upconversion.</title><author><name sortKey="Ishimatsu, Ryoichi" sort="Ishimatsu, Ryoichi" uniqKey="Ishimatsu R" first="Ryoichi" last="Ishimatsu">Ryoichi Ishimatsu</name><affiliation><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. ishimatsu@cstf.kyushu-u.ac.jp.</nlm:affiliation></affiliation></author><author><name sortKey="Edura, Tomohiko" sort="Edura, Tomohiko" uniqKey="Edura T" first="Tomohiko" last="Edura">Tomohiko Edura</name><affiliation><nlm:affiliation>Center for Organic Photonics and Electronics Research, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.</nlm:affiliation></affiliation></author><author><name sortKey="Adachi, Chihaya" sort="Adachi, Chihaya" uniqKey="Adachi C" first="Chihaya" last="Adachi">Chihaya Adachi</name><affiliation><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. adachi@opera.kyushu-u.ac.jp.</nlm:affiliation></affiliation></author><author><name sortKey="Nakano, Koji" sort="Nakano, Koji" uniqKey="Nakano K" first="Koji" last="Nakano">Koji Nakano</name><affiliation><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.</nlm:affiliation></affiliation></author><author><name sortKey="Imato, Toshihiko" sort="Imato, Toshihiko" uniqKey="Imato T" first="Toshihiko" last="Imato">Toshihiko Imato</name><affiliation><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. imato@cstf.kyushu-u.ac.jp.</nlm:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:26916843</idno><idno type="pmid">26916843</idno><idno type="doi">10.1002/chem.201600077</idno><idno type="wicri:Area/PubMed/Corpus">000012</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Photophysical Properties and Efficient, Stable, Electrogenerated Chemiluminescence of Donor-Acceptor Molecules Exhibiting Thermal Spin Upconversion.</title><author><name sortKey="Ishimatsu, Ryoichi" sort="Ishimatsu, Ryoichi" uniqKey="Ishimatsu R" first="Ryoichi" last="Ishimatsu">Ryoichi Ishimatsu</name><affiliation><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. ishimatsu@cstf.kyushu-u.ac.jp.</nlm:affiliation></affiliation></author><author><name sortKey="Edura, Tomohiko" sort="Edura, Tomohiko" uniqKey="Edura T" first="Tomohiko" last="Edura">Tomohiko Edura</name><affiliation><nlm:affiliation>Center for Organic Photonics and Electronics Research, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.</nlm:affiliation></affiliation></author><author><name sortKey="Adachi, Chihaya" sort="Adachi, Chihaya" uniqKey="Adachi C" first="Chihaya" last="Adachi">Chihaya Adachi</name><affiliation><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. adachi@opera.kyushu-u.ac.jp.</nlm:affiliation></affiliation></author><author><name sortKey="Nakano, Koji" sort="Nakano, Koji" uniqKey="Nakano K" first="Koji" last="Nakano">Koji Nakano</name><affiliation><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.</nlm:affiliation></affiliation></author><author><name sortKey="Imato, Toshihiko" sort="Imato, Toshihiko" uniqKey="Imato T" first="Toshihiko" last="Imato">Toshihiko Imato</name><affiliation><nlm:affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. imato@cstf.kyushu-u.ac.jp.</nlm:affiliation></affiliation></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="e-ISSN">1521-3765</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The photophysical properties and electrogenerated chemiluminescence (ECL) of three donor-acceptor molecules composed of dicyanobenzene and methyl-, tert-butyl-, and phenyl-substituted carbazolyl groups, 1,2,3,5-tetrakis(3,6-disubstituted-carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN-Me, 4CzIPN-tBu, and 4CzIPN-Ph, respectively) are described. These molecules show delayed fluorescence as a result of thermal spin upconversion from the lowest triplet state to the lowest singlet state at room temperature. The three molecules showed yellow to yellowish-red ECL. Remarkably, the ECL efficiencies of 4CzIPN-tBu in dichloromethane reached almost 40 %. Moreover, stable ECL was emitted from 4CzIPN-tBu and 4CzIPN-Ph. In case of 4CzIPN-Me, the ECL intensity decreased during voltage cycles because of polymerization. Quantum chemical calculations revealed that polymerization was inhibited by the steric hindrance of the bulky tert-butyl and phenyl groups on the carbazolyl moieties and lowered the spin density on the carbazolyl groups through electron conjugation for 4CzIPN-Ph.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="In-Data-Review"><PMID Version="1">26916843</PMID><DateCreated><Year>2016</Year><Month>03</Month><Day>21</Day></DateCreated><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3765</ISSN><JournalIssue CitedMedium="Internet"><Volume>22</Volume><Issue>14</Issue><PubDate><Year>2016</Year><Month>Mar</Month><Day>24</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Photophysical Properties and Efficient, Stable, Electrogenerated Chemiluminescence of Donor-Acceptor Molecules Exhibiting Thermal Spin Upconversion.</ArticleTitle><Pagination><MedlinePgn>4889-98</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/chem.201600077</ELocationID><Abstract><AbstractText>The photophysical properties and electrogenerated chemiluminescence (ECL) of three donor-acceptor molecules composed of dicyanobenzene and methyl-, tert-butyl-, and phenyl-substituted carbazolyl groups, 1,2,3,5-tetrakis(3,6-disubstituted-carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN-Me, 4CzIPN-tBu, and 4CzIPN-Ph, respectively) are described. These molecules show delayed fluorescence as a result of thermal spin upconversion from the lowest triplet state to the lowest singlet state at room temperature. The three molecules showed yellow to yellowish-red ECL. Remarkably, the ECL efficiencies of 4CzIPN-tBu in dichloromethane reached almost 40 %. Moreover, stable ECL was emitted from 4CzIPN-tBu and 4CzIPN-Ph. In case of 4CzIPN-Me, the ECL intensity decreased during voltage cycles because of polymerization. Quantum chemical calculations revealed that polymerization was inhibited by the steric hindrance of the bulky tert-butyl and phenyl groups on the carbazolyl moieties and lowered the spin density on the carbazolyl groups through electron conjugation for 4CzIPN-Ph.</AbstractText><CopyrightInformation>© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Ishimatsu</LastName><ForeName>Ryoichi</ForeName><Initials>R</Initials><AffiliationInfo><Affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. ishimatsu@cstf.kyushu-u.ac.jp.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Edura</LastName><ForeName>Tomohiko</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>Center for Organic Photonics and Electronics Research, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Adachi</LastName><ForeName>Chihaya</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. adachi@opera.kyushu-u.ac.jp.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Center for Organic Photonics and Electronics Research, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. adachi@opera.kyushu-u.ac.jp.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>JST, ERATO, Adachi Molecular Exciton Engineering Project, c/o Center for Organic Photonics and Electronics Research, and, International Institute for Carbon Neutral Energy, Research (WPI-I2CNER), Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. adachi@opera.kyushu-u.ac.jp.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Nakano</LastName><ForeName>Koji</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Imato</LastName><ForeName>Toshihiko</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan. imato@cstf.kyushu-u.ac.jp.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>02</Month><Day>24</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">donor-acceptor systems</Keyword><Keyword MajorTopicYN="N">electrochemiluminescence</Keyword><Keyword MajorTopicYN="N">fluorescence</Keyword><Keyword MajorTopicYN="N">lifetimes</Keyword><Keyword MajorTopicYN="N">solvent effects</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>1</Month><Day>8</Day></PubMedPubDate><PubMedPubDate PubStatus="aheadofprint"><Year>2016</Year><Month>2</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>2</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>2</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>2</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">26916843</ArticleId><ArticleId IdType="doi">10.1002/chem.201600077</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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