Carbo-biphenyls and Carbo-terphenyls: Oligo(phenylene ethynylene) Ring Carbo-mers.
Identifieur interne : 000996 ( PubMed/Checkpoint ); précédent : 000995; suivant : 000997Carbo-biphenyls and Carbo-terphenyls: Oligo(phenylene ethynylene) Ring Carbo-mers.
Auteurs : Chongwei Zhu [France] ; Albert Poater [Espagne] ; Carine Duhayon [France] ; Brice Kauffmann [France] ; Alix Saquet [France] ; Valérie Maraval [France] ; Remi Chauvin [France]Source :
- Angewandte Chemie (International ed. in English) [ 1521-3773 ] ; 2018.
Abstract
Ring carbo-mers of oligo(phenylene ethynylene)s (OPEn, n=0-2), made of C2 -catenated C18 carbo-benzene rings, have been synthesized and characterized by NMR and UV-vis spectroscopy, crystallography and voltammetry. Analyses of crystal and DFT-optimized structures show that the C18 rings preserve their individual aromatic character according to structural and magnetic criteria (NICS indices). Carbo-terphenyls (n=2) are reversibly reduced at ca. -0.42 V/SCE, i.e. 0.41 V more readily than the corresponding carbo-benzene (-0.83 V/SCE), thus revealing efficient inter-ring π-conjugation. An accurate linear fit of E1/2red1 vs. the DFT LUMO energy suggests a notably higher value (-0.30 V/SCE) for a carbo-quaterphenyl congener (n=3). Increase with n of the effective π-conjugation is also evidenced by a red shift of two of the three main visible light absorption bands, all being assigned to TDDFT-calculated excited states, one of them restricting to a HOMO→LUMO main one-electron transition.
DOI: 10.1002/anie.201713411
PubMed: 29504656
Affiliations:
- Espagne, France
- Aquitaine, Midi-Pyrénées, Nouvelle-Aquitaine, Occitanie (région administrative)
- Pessac, Toulouse
- Université de Bordeaux
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Carbo-mers.</title><author><name sortKey="Zhu, Chongwei" sort="Zhu, Chongwei" uniqKey="Zhu C" first="Chongwei" last="Zhu">Chongwei Zhu</name><affiliation wicri:level="3"><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author><author><name sortKey="Poater, Albert" sort="Poater, Albert" uniqKey="Poater A" first="Albert" last="Poater">Albert Poater</name><affiliation wicri:level="1"><nlm:affiliation>Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, Campus 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wicri:level="3"><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author><author><name sortKey="Maraval, Valerie" sort="Maraval, Valerie" uniqKey="Maraval V" first="Valérie" last="Maraval">Valérie Maraval</name><affiliation wicri:level="3"><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author><author><name sortKey="Chauvin, Remi" sort="Chauvin, Remi" uniqKey="Chauvin R" first="Remi" last="Chauvin">Remi Chauvin</name><affiliation wicri:level="3"><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4</wicri:regionArea><placeName><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Midi-Pyrénées</region><settlement type="city">Toulouse</settlement></placeName></affiliation></author></analytic><series><title level="j">Angewandte Chemie (International ed. in English)</title><idno type="eISSN">1521-3773</idno><imprint><date when="2018" type="published">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Ring carbo-mers of oligo(phenylene ethynylene)s (OPEn, n=0-2), made of C<sub>2</sub> -catenated C<sub>18</sub> carbo-benzene rings, have been synthesized and characterized by NMR and UV-vis spectroscopy, crystallography and voltammetry. Analyses of crystal and DFT-optimized structures show that the C<sub>18</sub> rings preserve their individual aromatic character according to structural and magnetic criteria (NICS indices). Carbo-terphenyls (n=2) are reversibly reduced at ca. -0.42 V/SCE, i.e. 0.41 V more readily than the corresponding carbo-benzene (-0.83 V/SCE), thus revealing efficient inter-ring π-conjugation. An accurate linear fit of E<sub>1/2</sub><sup>red1</sup> vs. the DFT LUMO energy suggests a notably higher value (-0.30 V/SCE) for a carbo-quaterphenyl congener (n=3). Increase with n of the effective π-conjugation is also evidenced by a red shift of two of the three main visible light absorption bands, all being assigned to TDDFT-calculated excited states, one of them restricting to a HOMO→LUMO main one-electron transition.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">29504656</PMID><DateRevised><Year>2019</Year><Month>11</Month><Day>20</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3773</ISSN><JournalIssue CitedMedium="Internet"><Volume>57</Volume><Issue>20</Issue><PubDate><Year>2018</Year><Month>05</Month><Day>14</Day></PubDate></JournalIssue><Title>Angewandte Chemie (International ed. in English)</Title><ISOAbbreviation>Angew. Chem. Int. Ed. Engl.</ISOAbbreviation></Journal><ArticleTitle>Carbo-biphenyls and Carbo-terphenyls: Oligo(phenylene ethynylene) Ring Carbo-mers.</ArticleTitle><Pagination><MedlinePgn>5640-5644</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/anie.201713411</ELocationID><Abstract><AbstractText>Ring carbo-mers of oligo(phenylene ethynylene)s (OPEn, n=0-2), made of C<sub>2</sub> -catenated C<sub>18</sub> carbo-benzene rings, have been synthesized and characterized by NMR and UV-vis spectroscopy, crystallography and voltammetry. Analyses of crystal and DFT-optimized structures show that the C<sub>18</sub> rings preserve their individual aromatic character according to structural and magnetic criteria (NICS indices). Carbo-terphenyls (n=2) are reversibly reduced at ca. -0.42 V/SCE, i.e. 0.41 V more readily than the corresponding carbo-benzene (-0.83 V/SCE), thus revealing efficient inter-ring π-conjugation. An accurate linear fit of E<sub>1/2</sub><sup>red1</sup> vs. the DFT LUMO energy suggests a notably higher value (-0.30 V/SCE) for a carbo-quaterphenyl congener (n=3). Increase with n of the effective π-conjugation is also evidenced by a red shift of two of the three main visible light absorption bands, all being assigned to TDDFT-calculated excited states, one of them restricting to a HOMO→LUMO main one-electron transition.</AbstractText><CopyrightInformation>© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Zhu</LastName><ForeName>Chongwei</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062, Toulouse Cedex 9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Poater</LastName><ForeName>Albert</ForeName><Initials>A</Initials><Identifier Source="ORCID">0000-0002-8997-2599</Identifier><AffiliationInfo><Affiliation>Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, Campus Montilivi, 17003, Girona, Catalonia, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Duhayon</LastName><ForeName>Carine</ForeName><Initials>C</Initials><Identifier Source="ORCID">0000-0001-7345-8782</Identifier><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062, Toulouse Cedex 9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kauffmann</LastName><ForeName>Brice</ForeName><Initials>B</Initials><Identifier Source="ORCID">0000-0002-2932-3255</Identifier><AffiliationInfo><Affiliation>Université de Bordeaux, CNRS, INSERM, UMS3033/US001, Institut Européen de Chimie et Biologie, 33607, Pessac, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Saquet</LastName><ForeName>Alix</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062, Toulouse Cedex 9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Maraval</LastName><ForeName>Valérie</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062, Toulouse Cedex 9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chauvin</LastName><ForeName>Remi</ForeName><Initials>R</Initials><Identifier Source="ORCID">0000-0002-4491-6390</Identifier><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP44099, 31077, Toulouse Cedex 4, France.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062, Toulouse Cedex 9, France.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2018</Year><Month>04</Month><Day>23</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Angew Chem Int Ed Engl</MedlineTA><NlmUniqueID>0370543</NlmUniqueID><ISSNLinking>1433-7851</ISSNLinking></MedlineJournalInfo><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">OPEs</Keyword><Keyword MajorTopicYN="Y">alkynes</Keyword><Keyword MajorTopicYN="Y">aromaticity</Keyword><Keyword MajorTopicYN="Y">bi-/terphenyl</Keyword><Keyword MajorTopicYN="Y">carbo-benzenes</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate 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Bordeaux</li></orgName></list><tree><country name="France"><region name="Occitanie (région administrative)"><name sortKey="Zhu, Chongwei" sort="Zhu, Chongwei" uniqKey="Zhu C" first="Chongwei" last="Zhu">Chongwei Zhu</name></region><name sortKey="Chauvin, Remi" sort="Chauvin, Remi" uniqKey="Chauvin R" first="Remi" last="Chauvin">Remi Chauvin</name><name sortKey="Duhayon, Carine" sort="Duhayon, Carine" uniqKey="Duhayon C" first="Carine" last="Duhayon">Carine Duhayon</name><name sortKey="Kauffmann, Brice" sort="Kauffmann, Brice" uniqKey="Kauffmann B" first="Brice" last="Kauffmann">Brice Kauffmann</name><name sortKey="Maraval, Valerie" sort="Maraval, Valerie" uniqKey="Maraval V" first="Valérie" last="Maraval">Valérie Maraval</name><name sortKey="Saquet, Alix" sort="Saquet, Alix" uniqKey="Saquet A" first="Alix" last="Saquet">Alix Saquet</name></country><country name="Espagne"><noRegion><name sortKey="Poater, Albert" sort="Poater, Albert" uniqKey="Poater A" first="Albert" 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