Wedge‐Shaped Molecules with a Sulfonate Group at the Tip—A New Class of Self‐Assembling Amphiphiles
Identifieur interne : 001319 ( Istex/Corpus ); précédent : 001318; suivant : 001320Wedge‐Shaped Molecules with a Sulfonate Group at the Tip—A New Class of Self‐Assembling Amphiphiles
Auteurs : Xiaomin Zhu ; Bernd Tartsch ; Uwe Beginn ; Martin MöllerSource :
- Chemistry – A European Journal [ 0947-6539 ] ; 2004-08-20.
Abstract
The synthesis of 4‐N‐[3′,4′,5′‐tris(dodecyloxy)benzamido]benzene‐4‐sulfonic acid (1) and 4′‐[3′′,4′′,5′′‐tris(dodecyloxy)benzoyloxy]azobenzene‐4‐sulfonic acid (2) is described. Pure acid 1 is stable, while 2 can be stored only in solution. Both acids were obtained from their sodium salts and were quantitatively transformed into the pyridinium salts. The phase behavior of these acids, as well as the sulfonates was investigated by differential scanning calorimetry and polarizing optical microscopy. The investigated compounds exhibit columnar mesophases. The formation of columnar superstructures was demonstrated for the sodium sulfonates by scanning force microscopy, gelation experiments, and proton magnetic resonance spectroscopy.
Wedge‐shaped sulfonate amphiphiles self‐assemble in bulk and from solution to give rodlike structures with circular cross‐sections (see picture); this causes the formation of columnar mesophases, as well as gelation of the solution. Phase diagram investigations demonstrate that the transition from the gel state to the highly ordered bulk phase occurs through a lyotropic mesophase.
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DOI: 10.1002/chem.200400050
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Pure acid 1 is stable, while 2 can be stored only in solution. Both acids were obtained from their sodium salts and were quantitatively transformed into the pyridinium salts. The phase behavior of these acids, as well as the sulfonates was investigated by differential scanning calorimetry and polarizing optical microscopy. The investigated compounds exhibit columnar mesophases. The formation of columnar superstructures was demonstrated for the sodium sulfonates by scanning force microscopy, gelation experiments, and proton magnetic resonance spectroscopy.</div><div type="abstract" xml:lang="en">Wedge‐shaped sulfonate amphiphiles self‐assemble in bulk and from solution to give rodlike structures with circular cross‐sections (see picture); this causes the formation of columnar mesophases, as well as gelation of the solution. 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<ref target="http://www.tei-c.org/">We use TEI</ref></desc></application></appInfo></encodingDesc><profileDesc><abstract xml:lang="en" style="main"><head>Abstract</head><p>The synthesis of 4‐<hi rend="italic">N</hi>‐[3′,4′,5′‐tris(dodecyloxy)benzamido]benzene‐4‐sulfonic acid (<hi rend="bold">1</hi>) and 4′‐[3′′,4′′,5′′‐tris(dodecyloxy)benzoyloxy]azobenzene‐4‐sulfonic acid (<hi rend="bold">2</hi>) is described. Pure acid <hi rend="bold">1</hi> is stable, while <hi rend="bold">2</hi> can be stored only in solution. Both acids were obtained from their sodium salts and were quantitatively transformed into the pyridinium salts. The phase behavior of these acids, as well as the sulfonates was investigated by differential scanning calorimetry and polarizing optical microscopy. The investigated compounds exhibit columnar mesophases. The formation of columnar superstructures was demonstrated for the sodium sulfonates by scanning force microscopy, gelation experiments, and proton magnetic resonance spectroscopy.</p></abstract><abstract xml:lang="en" style="graphical"><p><hi rend="bold">Wedge‐shaped sulfonate amphiphiles</hi> self‐assemble in bulk and from solution to give rodlike structures with circular cross‐sections (see picture); this causes the formation of columnar mesophases, as well as gelation of the solution. Phase diagram investigations demonstrate that the transition from the gel state to the highly ordered bulk phase occurs through a lyotropic mesophase.<figure type="box"><media mimeType="image" url="urn:x-wiley:09476539:media:CHEM200400050:content"></media><media mimeType="image/gif" url="" rendition="webLoRes"></media><media mimeType="image/gif" url="" rendition="webOriginal"></media><media mimeType="image/gif" url="" rendition="webHiRes"></media></figure></p></abstract><textClass><keywords xml:lang="en"><term xml:id="kwd1">amphiphiles</term><term xml:id="kwd2">mesophases</term><term xml:id="kwd3">self‐assembly</term><term xml:id="kwd4">sulfonic acids</term></keywords><keywords rend="articleCategory"><term>Full Paper</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc><revisionDesc><change when="2019-12-20" who="#istex" xml:id="pub2tei">formatting</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/ark:/67375/WNG-Z28ZVDHM-X/fulltext.txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en"><header><publicationMeta level="product"><publisherInfo><publisherName>WILEY‐VCH Verlag</publisherName><publisherLoc>Weinheim</publisherLoc></publisherInfo><doi registered="yes">10.1002/(ISSN)1521-3765</doi><issn type="print">0947-6539</issn><issn type="electronic">1521-3765</issn><idGroup><id type="product" value="CHEM"></id></idGroup><titleGroup><title type="main" xml:lang="en">Chemistry – A European Journal</title><title type="short">Chemistry – A European Journal</title></titleGroup></publicationMeta><publicationMeta level="part" position="160"><doi origin="wiley" registered="yes">10.1002/chem.v10:16</doi><numberingGroup><numbering type="journalVolume" number="10">10</numbering><numbering type="journalIssue">16</numbering></numberingGroup><coverDate startDate="2004-08-20">August 20, 2004</coverDate></publicationMeta><publicationMeta level="unit" type="article" position="6" status="forIssue"><doi origin="wiley" registered="yes">10.1002/chem.200400050</doi><idGroup><id type="unit" value="CHEM200400050"></id></idGroup><countGroup><count type="pageTotal" number="8"></count></countGroup><titleGroup><title type="articleCategory">Full Paper</title></titleGroup><copyright ownership="publisher">Copyright © 2004 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="firstOnline" date="2004-06-24"></event><event type="publishedOnlineFinalForm" date="2004-08-12"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.3.6 mode:FullText source:FullText result:FullText mathml2tex" date="2010-05-18"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-09"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-15"></event></eventGroup><numberingGroup><numbering type="pageFirst">3871</numbering><numbering type="pageLast">3878</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:CHEM.CHEM200400050.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="11"></count><count type="tableTotal" number="2"></count><count type="referenceTotal" number="33"></count></countGroup><titleGroup><title type="main" xml:lang="en">Wedge‐Shaped Molecules with a Sulfonate Group at the Tip—A New Class of Self‐Assembling Amphiphiles</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Xiaomin</givenNames><familyName>Zhu</familyName><degrees>Dr.</degrees></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#ab"><personName><givenNames>Bernd</givenNames><familyName>Tartsch</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Uwe</givenNames><familyName>Beginn</familyName><degrees>Dr.</degrees></personName><contactDetails><email normalForm="uwe.beginn@texmc.rwth-aachen.de">uwe.beginn@texmc.rwth‐aachen.de</email></contactDetails></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Martin</givenNames><familyName>Möller</familyName><degrees>Prof. Dr.</degrees></personName><contactDetails><email normalForm="moeller@dwi.rwth-aachen.de">moeller@dwi.rwth‐aachen.de</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="aa" countryCode="DE" type="organization"><unparsedAffiliation>Institut für Technische Chemie und Makromolekulare Chemie, Lehrstuhl für Textilchemie und Makromolekulare Chemie der RWTH Aachen, Worringerweg 1, 52056 Aachen, Germany, Fax: (+49) 241‐80‐22185</unparsedAffiliation></affiliation><affiliation xml:id="ab" countryCode="DE" type="organization"><unparsedAffiliation>Abteilung Organische Chemie III/Makromolekulare Chemie, Universität Ulm, Albert‐Einstein‐Allee 11, 89069 Ulm, Germany</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">amphiphiles</keyword><keyword xml:id="kwd2">mesophases</keyword><keyword xml:id="kwd3">self‐assembly</keyword><keyword xml:id="kwd4">sulfonic acids</keyword></keywordGroup><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>The synthesis of 4‐<i>N</i>‐[3′,4′,5′‐tris(dodecyloxy)benzamido]benzene‐4‐sulfonic acid (<b>1</b>) and 4′‐[3′′,4′′,5′′‐tris(dodecyloxy)benzoyloxy]azobenzene‐4‐sulfonic acid (<b>2</b>) is described. Pure acid <b>1</b> is stable, while <b>2</b> can be stored only in solution. Both acids were obtained from their sodium salts and were quantitatively transformed into the pyridinium salts. The phase behavior of these acids, as well as the sulfonates was investigated by differential scanning calorimetry and polarizing optical microscopy. The investigated compounds exhibit columnar mesophases. The formation of columnar superstructures was demonstrated for the sodium sulfonates by scanning force microscopy, gelation experiments, and proton magnetic resonance spectroscopy.</p></abstract><abstract type="graphical" xml:lang="en"><p><b>Wedge‐shaped sulfonate amphiphiles</b> self‐assemble in bulk and from solution to give rodlike structures with circular cross‐sections (see picture); this causes the formation of columnar mesophases, as well as gelation of the solution. Phase diagram investigations demonstrate that the transition from the gel state to the highly ordered bulk phase occurs through a lyotropic mesophase.<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:09476539:media:CHEM200400050:content"></mediaResource><mediaResource alt="thumbnail image" rendition="webLoRes" mimeType="image/gif" href=""></mediaResource><mediaResource alt="original image" rendition="webOriginal" mimeType="image/gif" href=""></mediaResource><mediaResource alt="magnified image" rendition="webHiRes" mimeType="image/gif" href=""></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Wedge‐Shaped Molecules with a Sulfonate Group at the Tip—A New Class of Self‐Assembling Amphiphiles</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Wedge‐Shaped Molecules with a Sulfonate Group at the Tip—A New Class of Self‐Assembling Amphiphiles</title></titleInfo><name type="personal"><namePart type="given">Xiaomin</namePart><namePart type="family">Zhu</namePart><namePart type="termsOfAddress">Dr.</namePart><affiliation>Institut für Technische Chemie und Makromolekulare Chemie, Lehrstuhl für Textilchemie und Makromolekulare Chemie der RWTH Aachen, Worringerweg 1, 52056 Aachen, Germany, Fax: (+49) 241‐80‐22185</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Bernd</namePart><namePart type="family">Tartsch</namePart><affiliation>Abteilung Organische Chemie III/Makromolekulare Chemie, Universität Ulm, Albert‐Einstein‐Allee 11, 89069 Ulm, Germany</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Uwe</namePart><namePart type="family">Beginn</namePart><namePart type="termsOfAddress">Dr.</namePart><affiliation>Institut für Technische Chemie und Makromolekulare Chemie, Lehrstuhl für Textilchemie und Makromolekulare Chemie der RWTH Aachen, Worringerweg 1, 52056 Aachen, Germany, Fax: (+49) 241‐80‐22185</affiliation><affiliation>E-mail: uwe.beginn@texmc.rwth‐aachen.de</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Martin</namePart><namePart type="family">Möller</namePart><namePart type="termsOfAddress">Prof. Dr.</namePart><affiliation>Institut für Technische Chemie und Makromolekulare Chemie, Lehrstuhl für Textilchemie und Makromolekulare Chemie der RWTH Aachen, Worringerweg 1, 52056 Aachen, Germany, Fax: (+49) 241‐80‐22185</affiliation><affiliation>E-mail: moeller@dwi.rwth‐aachen.de</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2004-08-20</dateIssued><copyrightDate encoding="w3cdtf">2004</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">11</extent><extent unit="tables">2</extent><extent unit="references">33</extent></physicalDescription><abstract lang="en">The synthesis of 4‐N‐[3′,4′,5′‐tris(dodecyloxy)benzamido]benzene‐4‐sulfonic acid (1) and 4′‐[3′′,4′′,5′′‐tris(dodecyloxy)benzoyloxy]azobenzene‐4‐sulfonic acid (2) is described. Pure acid 1 is stable, while 2 can be stored only in solution. Both acids were obtained from their sodium salts and were quantitatively transformed into the pyridinium salts. The phase behavior of these acids, as well as the sulfonates was investigated by differential scanning calorimetry and polarizing optical microscopy. The investigated compounds exhibit columnar mesophases. The formation of columnar superstructures was demonstrated for the sodium sulfonates by scanning force microscopy, gelation experiments, and proton magnetic resonance spectroscopy.</abstract><abstract type="graphical" lang="en">Wedge‐shaped sulfonate amphiphiles self‐assemble in bulk and from solution to give rodlike structures with circular cross‐sections (see picture); this causes the formation of columnar mesophases, as well as gelation of the solution. Phase diagram investigations demonstrate that the transition from the gel state to the highly ordered bulk phase occurs through a lyotropic mesophase.</abstract><subject lang="en"><genre>keywords</genre><topic>amphiphiles</topic><topic>mesophases</topic><topic>self‐assembly</topic><topic>sulfonic acids</topic></subject><relatedItem type="host"><titleInfo><title>Chemistry – A European Journal</title></titleInfo><titleInfo type="abbreviated"><title>Chemistry – A European Journal</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><subject><genre>article-category</genre><topic>Full Paper</topic></subject><identifier type="ISSN">0947-6539</identifier><identifier type="eISSN">1521-3765</identifier><identifier type="DOI">10.1002/(ISSN)1521-3765</identifier><identifier type="PublisherID">CHEM</identifier><part><date>2004</date><detail type="volume"><caption>vol.</caption><number>10</number></detail><detail type="issue"><caption>no.</caption><number>16</number></detail><extent unit="pages"><start>3871</start><end>3878</end><total>8</total></extent></part></relatedItem><relatedItem type="references" displayLabel="cit1"><titleInfo><title> </title></titleInfo><genre>other</genre></relatedItem><relatedItem type="references" displayLabel="cit2"><titleInfo><title>S. 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