Synthesis and photochemical properties of novel pentamethylated norbornadiene containing polyimides
Identifieur interne : 000F71 ( Istex/Corpus ); précédent : 000F70; suivant : 000F72Synthesis and photochemical properties of novel pentamethylated norbornadiene containing polyimides
Auteurs : Ahmed Oueslati ; Hatem Ben Romdhane ; Vincent Martin ; Fréderic Schiets ; Régis Mercier ; Refaât ChaâbouniSource :
- Journal of Polymer Science Part A: Polymer Chemistry [ 0887-624X ] ; 2011-05-01.
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- KwdEn :
Abstract
A novel pentamethylated norbornadiene (NBD) based dianhydride, α,α′‐bis‐(3,4,5,6,7‐pentamethylcyclopenta‐2,4‐dienyl)meta‐xylene‐1,2‐dianhydride (3), was prepared from α,α′‐bis‐(pentamethylcyclopentadienyl)meta‐xylene (1) and acetylene dicarboxylic acid. The bis‐adduct formed via Diels–Alder reaction afforded tetra‐acid (2), which was chemically cyclodehydrated to lead the targeted dianhydride (3). New polyimides containing NBD moieties in the main chain were prepared from the dianhydride monomer (3) and various aromatic diamines. The chemical structure of the polymers was confirmed by both 1H and 13C NMR analysis. Their Molecular weights were also measured by SEC. All of these polyimides are soluble at room temperature in common organic solvents, such as chloroform, dichloromethane, THF, DMSO, DMF, and NMP, and show good thermal stabilities. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. It was found that the kinetic rate of the conversion NBD‐QC which proceeded smoothly is a first kinetic order. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement and were found to be around 90 kJ mol−1. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011
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DOI: 10.1002/pola.24626
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ISTEX:039BCCA6650FDBCF267F94BBCB4E4B85943576F4Le document en format XML
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The bis‐adduct formed via Diels–Alder reaction afforded tetra‐acid (2), which was chemically cyclodehydrated to lead the targeted dianhydride (3). New polyimides containing NBD moieties in the main chain were prepared from the dianhydride monomer (3) and various aromatic diamines. The chemical structure of the polymers was confirmed by both 1H and 13C NMR analysis. Their Molecular weights were also measured by SEC. All of these polyimides are soluble at room temperature in common organic solvents, such as chloroform, dichloromethane, THF, DMSO, DMF, and NMP, and show good thermal stabilities. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. It was found that the kinetic rate of the conversion NBD‐QC which proceeded smoothly is a first kinetic order. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement and were found to be around 90 kJ mol−1. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Ahmed Oueslati</name><affiliations><json:string>Unité de Recherche Synthèse et Analyse de Matériaux‐Département de Génie Industriel, École Nationale d'Ingénieurs de Tunis/Université de Tunis El Manar‐BP 37, Le Belvédère‐Tunis 1002, Tunisia</json:string></affiliations></json:item><json:item><name>Hatem Ben Romdhane</name><affiliations><json:string>Laboratoire de Chimie Organique Structurale‐Synthèse et Études Physico‐Chimiques, Faculté des Sciences de Tunis/Université de Tunis El Manar, Campus Universitaire, El Manar 2092, Tunisia</json:string></affiliations></json:item><json:item><name>Vincent Martin</name><affiliations><json:string>LEPMI/LMOPS, UMR5279 CNRS/ INP Grenoble, Chemin du Canal‐69360 Solaize, France</json:string></affiliations></json:item><json:item><name>Fréderic Schiets</name><affiliations><json:string>LEPMI/LMOPS, UMR5279 CNRS/ INP Grenoble, Chemin du Canal‐69360 Solaize, France</json:string></affiliations></json:item><json:item><name>Régis Mercier</name><affiliations><json:string>LEPMI/LMOPS, UMR5279 CNRS/ INP Grenoble, Chemin du Canal‐69360 Solaize, France</json:string></affiliations></json:item><json:item><name>Refaât Chaâbouni</name><affiliations><json:string>Unité de Recherche Synthèse et Analyse de Matériaux‐Département de Génie Industriel, École Nationale d'Ingénieurs de Tunis/Université de Tunis El Manar‐BP 37, Le Belvédère‐Tunis 1002, Tunisia</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>irradiation</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>isomerization</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>norbornadiene</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>polyimides</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>quadricyclane</value></json:item></subject><articleId><json:string>POLA24626</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><abstract>A novel pentamethylated norbornadiene (NBD) based dianhydride, α,α′‐bis‐(3,4,5,6,7‐pentamethylcyclopenta‐2,4‐dienyl)meta‐xylene‐1,2‐dianhydride (3), was prepared from α,α′‐bis‐(pentamethylcyclopentadienyl)meta‐xylene (1) and acetylene dicarboxylic acid. The bis‐adduct formed via Diels–Alder reaction afforded tetra‐acid (2), which was chemically cyclodehydrated to lead the targeted dianhydride (3). New polyimides containing NBD moieties in the main chain were prepared from the dianhydride monomer (3) and various aromatic diamines. The chemical structure of the polymers was confirmed by both 1H and 13C NMR analysis. Their Molecular weights were also measured by SEC. All of these polyimides are soluble at room temperature in common organic solvents, such as chloroform, dichloromethane, THF, DMSO, DMF, and NMP, and show good thermal stabilities. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. It was found that the kinetic rate of the conversion NBD‐QC which proceeded smoothly is a first kinetic order. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement and were found to be around 90 kJ mol−1. © 2011 Wiley Periodicals, Inc. 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The bis‐adduct formed via Diels–Alder reaction afforded tetra‐acid (2), which was chemically cyclodehydrated to lead the targeted dianhydride (3). New polyimides containing NBD moieties in the main chain were prepared from the dianhydride monomer (3) and various aromatic diamines. The chemical structure of the polymers was confirmed by both 1H and 13C NMR analysis. Their Molecular weights were also measured by SEC. All of these polyimides are soluble at room temperature in common organic solvents, such as chloroform, dichloromethane, THF, DMSO, DMF, and NMP, and show good thermal stabilities. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. It was found that the kinetic rate of the conversion NBD‐QC which proceeded smoothly is a first kinetic order. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement and were found to be around 90 kJ mol−1. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011</p></abstract><abstract xml:lang="en" style="graphical"><p>The synthesis and the characterization of new polyimides containing pentamethylated norbornadiene (NBD) moieties in the main chain from a new synthesized dianhydride monomer and various aromatic diamines are described. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement. 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creatorRole="author" affiliationRef="#af3"><personName><givenNames>Vincent</givenNames><familyName>Martin</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af3"><personName><givenNames>Fréderic</givenNames><familyName>Schiets</familyName></personName></creator><creator xml:id="au5" creatorRole="author" affiliationRef="#af3" corresponding="yes"><personName><givenNames>Régis</givenNames><familyName>Mercier</familyName></personName><contactDetails><email>mercier@lmops.cnrs.fr</email></contactDetails></creator><creator xml:id="au6" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Refaât</givenNames><familyName>Chaâbouni</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="TN" type="organization"><unparsedAffiliation>Unité de Recherche Synthèse et Analyse de Matériaux‐Département de Génie Industriel, École Nationale d'Ingénieurs de Tunis/Université de Tunis El Manar‐BP 37, Le Belvédère‐Tunis 1002, Tunisia</unparsedAffiliation></affiliation><affiliation xml:id="af2" countryCode="TN" type="organization"><unparsedAffiliation>Laboratoire de Chimie Organique Structurale‐Synthèse et Études Physico‐Chimiques, Faculté des Sciences de Tunis/Université de Tunis El Manar, Campus Universitaire, El Manar 2092, Tunisia</unparsedAffiliation></affiliation><affiliation xml:id="af3" countryCode="FR" type="organization"><unparsedAffiliation>LEPMI/LMOPS, UMR5279 CNRS/ INP Grenoble, Chemin du Canal‐69360 Solaize, France</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">irradiation</keyword><keyword xml:id="kwd2">isomerization</keyword><keyword xml:id="kwd3">norbornadiene</keyword><keyword xml:id="kwd4">polyimides</keyword><keyword xml:id="kwd5">quadricyclane</keyword></keywordGroup><fundingInfo><fundingAgency>French‐Tunisian CMCU (Comité Mixte de Coopération Universitaire Franco‐tunisien)</fundingAgency></fundingInfo><fundingInfo><fundingAgency>CNRS</fundingAgency></fundingInfo><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>A novel pentamethylated norbornadiene (NBD) based dianhydride, α,α′‐bis‐(3,4,5,6,7‐pentamethylcyclopenta‐2,4‐dienyl)meta‐xylene‐1,2‐dianhydride (3), was prepared from α,α′‐bis‐(pentamethylcyclopentadienyl)meta‐xylene (1) and acetylene dicarboxylic acid. The bis‐adduct formed via Diels–Alder reaction afforded tetra‐acid (2), which was chemically cyclodehydrated to lead the targeted dianhydride (3). New polyimides containing NBD moieties in the main chain were prepared from the dianhydride monomer (3) and various aromatic diamines. The chemical structure of the polymers was confirmed by both <sup>1</sup>H and <sup>13</sup>C NMR analysis. Their Molecular weights were also measured by SEC. All of these polyimides are soluble at room temperature in common organic solvents, such as chloroform, dichloromethane, THF, DMSO, DMF, and NMP, and show good thermal stabilities. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. It was found that the kinetic rate of the conversion NBD‐QC which proceeded smoothly is a first kinetic order. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement and were found to be around 90 kJ mol<sup>−1</sup>. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011</p></abstract><abstract type="graphical" xml:lang="en"><p>The synthesis and the characterization of new polyimides containing pentamethylated norbornadiene (NBD) moieties in the main chain from a new synthesized dianhydride monomer and various aromatic diamines are described. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement. The photochemical behavior of these novel polyimides under visible sunlight irradiation shows that they have both photoreactivity and capacity for heat storage.</p><p><blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="Wiley Periodicals, Inc." href="urn:x-wiley:0887624X:media:POLA24626:gra001"></mediaResource><mediaResource alt="thumbnail image" rendition="webLoRes" mimeType="image/gif" href=""></mediaResource><mediaResource alt="original image" rendition="webOriginal" mimeType="image/jpeg" href=""></mediaResource><mediaResource alt="magnified image" rendition="webHiRes" mimeType="image/jpeg" href=""></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Synthesis and photochemical properties of novel pentamethylated norbornadiene containing polyimides</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Novel Norbornadiene Containing Polyimides</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Synthesis and photochemical properties of novel pentamethylated norbornadiene containing polyimides</title></titleInfo><name type="personal"><namePart type="given">Ahmed</namePart><namePart type="family">Oueslati</namePart><affiliation>Unité de Recherche Synthèse et Analyse de Matériaux‐Département de Génie Industriel, École Nationale d'Ingénieurs de Tunis/Université de Tunis El Manar‐BP 37, Le Belvédère‐Tunis 1002, Tunisia</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Hatem</namePart><namePart type="family">Ben Romdhane</namePart><affiliation>Laboratoire de Chimie Organique Structurale‐Synthèse et Études Physico‐Chimiques, Faculté des Sciences de Tunis/Université de Tunis El Manar, Campus Universitaire, El Manar 2092, Tunisia</affiliation><description>Correspondence: Laboratoire de Chimie Organique Structurale‐ Synthèse et Études Physico‐chimiques, Faculté des Sciences de Tunis/Université de Tunis El Manar, Campus Universitaire, El Manar 2092, Tunisia</description><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Vincent</namePart><namePart type="family">Martin</namePart><affiliation>LEPMI/LMOPS, UMR5279 CNRS/ INP Grenoble, Chemin du Canal‐69360 Solaize, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Fréderic</namePart><namePart type="family">Schiets</namePart><affiliation>LEPMI/LMOPS, UMR5279 CNRS/ INP Grenoble, Chemin du Canal‐69360 Solaize, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Régis</namePart><namePart type="family">Mercier</namePart><affiliation>LEPMI/LMOPS, UMR5279 CNRS/ INP Grenoble, Chemin du Canal‐69360 Solaize, France</affiliation><description>Correspondence: Laboratoire de Chimie Organique Structurale‐ Synthèse et Études Physico‐chimiques, Faculté des Sciences de Tunis/Université de Tunis El Manar, Campus Universitaire, El Manar 2092, Tunisia</description><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Refaât</namePart><namePart type="family">Chaâbouni</namePart><affiliation>Unité de Recherche Synthèse et Analyse de Matériaux‐Département de Génie Industriel, École Nationale d'Ingénieurs de Tunis/Université de Tunis El Manar‐BP 37, Le Belvédère‐Tunis 1002, Tunisia</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article"></genre><originInfo><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><place><placeTerm type="text">Hoboken</placeTerm></place><dateIssued encoding="w3cdtf">2011-05-01</dateIssued><dateCaptured encoding="w3cdtf">2010-11-29</dateCaptured><dateValid encoding="w3cdtf">2011-02-05</dateValid><copyrightDate encoding="w3cdtf">2011</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType><extent unit="figures">14</extent><extent unit="tables">4</extent><extent unit="references">34</extent><extent unit="words">6579</extent></physicalDescription><abstract lang="en">A novel pentamethylated norbornadiene (NBD) based dianhydride, α,α′‐bis‐(3,4,5,6,7‐pentamethylcyclopenta‐2,4‐dienyl)meta‐xylene‐1,2‐dianhydride (3), was prepared from α,α′‐bis‐(pentamethylcyclopentadienyl)meta‐xylene (1) and acetylene dicarboxylic acid. The bis‐adduct formed via Diels–Alder reaction afforded tetra‐acid (2), which was chemically cyclodehydrated to lead the targeted dianhydride (3). New polyimides containing NBD moieties in the main chain were prepared from the dianhydride monomer (3) and various aromatic diamines. The chemical structure of the polymers was confirmed by both 1H and 13C NMR analysis. Their Molecular weights were also measured by SEC. All of these polyimides are soluble at room temperature in common organic solvents, such as chloroform, dichloromethane, THF, DMSO, DMF, and NMP, and show good thermal stabilities. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. It was found that the kinetic rate of the conversion NBD‐QC which proceeded smoothly is a first kinetic order. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement and were found to be around 90 kJ mol−1. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011</abstract><abstract type="graphical" lang="en">The synthesis and the characterization of new polyimides containing pentamethylated norbornadiene (NBD) moieties in the main chain from a new synthesized dianhydride monomer and various aromatic diamines are described. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement. The photochemical behavior of these novel polyimides under visible sunlight irradiation shows that they have both photoreactivity and capacity for heat storage.</abstract><note type="funding">French‐Tunisian CMCU (Comité Mixte de Coopération Universitaire Franco‐tunisien)</note><note type="funding">CNRS</note><subject lang="en"><genre>keywords</genre><topic>irradiation</topic><topic>isomerization</topic><topic>norbornadiene</topic><topic>polyimides</topic><topic>quadricyclane</topic></subject><relatedItem type="host"><titleInfo><title>Journal of Polymer Science Part A: Polymer Chemistry</title></titleInfo><titleInfo type="abbreviated"><title>J. Polym. Sci. A Polym. Chem.</title></titleInfo><genre type="journal">journal</genre><subject><genre>article-category</genre><topic>Article</topic></subject><identifier type="ISSN">0887-624X</identifier><identifier type="eISSN">1099-0518</identifier><identifier type="DOI">10.1002/(ISSN)1099-0518</identifier><identifier type="PublisherID">POLA</identifier><part><date>2011</date><detail type="volume"><caption>vol.</caption><number>49</number></detail><detail type="issue"><caption>no.</caption><number>9</number></detail><extent unit="pages"><start>1988</start><end>1998</end><total>11</total></extent></part></relatedItem><identifier type="istex">039BCCA6650FDBCF267F94BBCB4E4B85943576F4</identifier><identifier type="DOI">10.1002/pola.24626</identifier><identifier type="ArticleID">POLA24626</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2011 Wiley Periodicals, Inc.</accessCondition><recordInfo><recordContentSource>WILEY</recordContentSource><recordOrigin>Wiley Subscription Services, Inc., A Wiley Company</recordOrigin></recordInfo></mods></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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