Difluorenyl carbo-Benzenes: Synthesis, Electronic Structure, and Two-Photon Absorption Properties of Hydrocarbon Quadrupolar Chromophores.
Identifieur interne : 001511 ( PubMed/Curation ); précédent : 001510; suivant : 001512Difluorenyl carbo-Benzenes: Synthesis, Electronic Structure, and Two-Photon Absorption Properties of Hydrocarbon Quadrupolar Chromophores.
Auteurs : Iaroslav Baglai ; Manuel De Anda-Villa ; Rodrigo M. Barba-Barba ; Corentin Poidevin ; Gabriel Ramos-Ortíz [Mexique] ; Valérie Maraval [France] ; Christine Lepetit ; Nathalie Saffon-Merceron ; José-Luis Maldonado ; Remi Chauvin [France]Source :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2015.
Abstract
The synthesis, crystal and electronic structures, and one- and two-photon absorption properties of two quadrupolar fluorenyl-substituted tetraphenyl carbo-benzenes are described. These all-hydrocarbon chromophores, differing in the nature of the linkers between the fluorenyl substituents and the carbo-benzene core (C-C bonds for 3 a, C-C=C-C expanders for 3 b), exhibit quasi-superimposable one-photon absorption (1PA) spectra but different two-photon absorption (2PA) cross-sections σ2PA. Z-scan measurements (under NIR femtosecond excitation) indeed showed that the C≡C expansion results in an approximately twofold increase in the σ2PA value, from 336 to 656 GM (1 GM = 10(-50) cm(4) s molecule(-1) photon(-1)) at λ = 800 nm. The first excited states of Au and Ag symmetry accounting for 1PA and 2PA, respectively, were calculated at the TDDFT level of theory and used for sum-over-state estimations of σ2PA(λi), in which λi = 2 hc/Ei, h is Planck's constant, c is the speed of light, and Ei is the energy of the 2PA-allowed transition. The calculated σ2PA values of 227 GM at 687 nm for 3 a and 349 GM at 708 nm for 3 b are in agreement with the Z-scan results.
DOI: 10.1002/chem.201500482
PubMed: 26267308
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Iaroslav Baglai<affiliation><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France).</nlm:affiliation><wicri:noCountry code="subField">31077 Toulouse CEDEX 4 (France)</wicri:noCountry></affiliation><affiliation><nlm:affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</nlm:affiliation><wicri:noCountry code="subField">Fax: (+33) 5-61-55-30-03</wicri:noCountry></affiliation><affiliation><nlm:affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</nlm:affiliation><wicri:noCountry code="subField">Fax: (+33) 5-61-55-30-03</wicri:noCountry></affiliation><affiliation><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France).</nlm:affiliation><wicri:noCountry code="subField">31077 Toulouse CEDEX 4 (France)</wicri:noCountry></affiliation><affiliation><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France).</nlm:affiliation><wicri:noCountry code="subField">31077 Toulouse CEDEX 4 (France)</wicri:noCountry></affiliation><affiliation><nlm:affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse CEDEX 9 (France).</nlm:affiliation><wicri:noCountry code="subField">31062 Toulouse CEDEX 9 (France)</wicri:noCountry></affiliation><affiliation><nlm:affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</nlm:affiliation><wicri:noCountry code="subField">Fax: (+33) 5-61-55-30-03</wicri:noCountry></affiliation>Le document en format XML
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(México), Fax: (+33) 5-61-55-30-03. garamoso@cio.mx.</nlm:affiliation><country wicri:rule="url">Mexique</country></affiliation></author><author><name sortKey="Maraval, Valerie" sort="Maraval, Valerie" uniqKey="Maraval V" first="Valérie" last="Maraval">Valérie Maraval</name><affiliation wicri:level="1"><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France). chauvin@lcc-toulouse.fr.</nlm:affiliation><country wicri:rule="url">France</country></affiliation></author><author><name sortKey="Lepetit, Christine" sort="Lepetit, Christine" uniqKey="Lepetit C" first="Christine" last="Lepetit">Christine Lepetit</name><affiliation><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France).</nlm:affiliation><wicri:noCountry code="subField">31077 Toulouse CEDEX 4 (France)</wicri:noCountry></affiliation></author><author><name sortKey="Saffon Merceron, Nathalie" sort="Saffon Merceron, Nathalie" uniqKey="Saffon Merceron N" first="Nathalie" last="Saffon-Merceron">Nathalie Saffon-Merceron</name><affiliation><nlm:affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse CEDEX 9 (France).</nlm:affiliation><wicri:noCountry code="subField">31062 Toulouse CEDEX 9 (France)</wicri:noCountry></affiliation></author><author><name sortKey="Maldonado, Jose Luis" sort="Maldonado, Jose Luis" uniqKey="Maldonado J" first="José-Luis" last="Maldonado">José-Luis Maldonado</name><affiliation><nlm:affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</nlm:affiliation><wicri:noCountry code="subField">Fax: (+33) 5-61-55-30-03</wicri:noCountry></affiliation></author><author><name sortKey="Chauvin, Remi" sort="Chauvin, Remi" uniqKey="Chauvin R" first="Remi" last="Chauvin">Remi Chauvin</name><affiliation wicri:level="1"><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France). valerie.maraval@lcc-toulouse.fr.</nlm:affiliation><country wicri:rule="url">France</country></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2015">2015</date><idno type="RBID">pubmed:26267308</idno><idno type="pmid">26267308</idno><idno type="doi">10.1002/chem.201500482</idno><idno type="wicri:Area/PubMed/Corpus">001511</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001511</idno><idno type="wicri:Area/PubMed/Curation">001511</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">001511</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Difluorenyl carbo-Benzenes: Synthesis, Electronic Structure, and Two-Photon Absorption Properties of Hydrocarbon Quadrupolar Chromophores.</title><author><name sortKey="Baglai, Iaroslav" sort="Baglai, Iaroslav" uniqKey="Baglai I" first="Iaroslav" last="Baglai">Iaroslav Baglai</name><affiliation><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France).</nlm:affiliation><wicri:noCountry code="subField">31077 Toulouse CEDEX 4 (France)</wicri:noCountry></affiliation></author><author><name sortKey="De Anda Villa, Manuel" sort="De Anda Villa, Manuel" uniqKey="De Anda Villa M" first="Manuel" last="De Anda-Villa">Manuel De Anda-Villa</name><affiliation><nlm:affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</nlm:affiliation><wicri:noCountry code="subField">Fax: (+33) 5-61-55-30-03</wicri:noCountry></affiliation></author><author><name sortKey="Barba Barba, Rodrigo M" sort="Barba Barba, Rodrigo M" uniqKey="Barba Barba R" first="Rodrigo M" last="Barba-Barba">Rodrigo M. Barba-Barba</name><affiliation><nlm:affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</nlm:affiliation><wicri:noCountry code="subField">Fax: (+33) 5-61-55-30-03</wicri:noCountry></affiliation></author><author><name sortKey="Poidevin, Corentin" sort="Poidevin, Corentin" uniqKey="Poidevin C" first="Corentin" last="Poidevin">Corentin Poidevin</name><affiliation><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France).</nlm:affiliation><wicri:noCountry code="subField">31077 Toulouse CEDEX 4 (France)</wicri:noCountry></affiliation></author><author><name sortKey="Ramos Ortiz, Gabriel" sort="Ramos Ortiz, Gabriel" uniqKey="Ramos Ortiz G" first="Gabriel" last="Ramos-Ortíz">Gabriel Ramos-Ortíz</name><affiliation wicri:level="1"><nlm:affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03. garamoso@cio.mx.</nlm:affiliation><country wicri:rule="url">Mexique</country></affiliation></author><author><name sortKey="Maraval, Valerie" sort="Maraval, Valerie" uniqKey="Maraval V" first="Valérie" last="Maraval">Valérie Maraval</name><affiliation wicri:level="1"><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France). chauvin@lcc-toulouse.fr.</nlm:affiliation><country wicri:rule="url">France</country></affiliation></author><author><name sortKey="Lepetit, Christine" sort="Lepetit, Christine" uniqKey="Lepetit C" first="Christine" last="Lepetit">Christine Lepetit</name><affiliation><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France).</nlm:affiliation><wicri:noCountry code="subField">31077 Toulouse CEDEX 4 (France)</wicri:noCountry></affiliation></author><author><name sortKey="Saffon Merceron, Nathalie" sort="Saffon Merceron, Nathalie" uniqKey="Saffon Merceron N" first="Nathalie" last="Saffon-Merceron">Nathalie Saffon-Merceron</name><affiliation><nlm:affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse CEDEX 9 (France).</nlm:affiliation><wicri:noCountry code="subField">31062 Toulouse CEDEX 9 (France)</wicri:noCountry></affiliation></author><author><name sortKey="Maldonado, Jose Luis" sort="Maldonado, Jose Luis" uniqKey="Maldonado J" first="José-Luis" last="Maldonado">José-Luis Maldonado</name><affiliation><nlm:affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</nlm:affiliation><wicri:noCountry code="subField">Fax: (+33) 5-61-55-30-03</wicri:noCountry></affiliation></author><author><name sortKey="Chauvin, Remi" sort="Chauvin, Remi" uniqKey="Chauvin R" first="Remi" last="Chauvin">Remi Chauvin</name><affiliation wicri:level="1"><nlm:affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France). valerie.maraval@lcc-toulouse.fr.</nlm:affiliation><country wicri:rule="url">France</country></affiliation></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="eISSN">1521-3765</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The synthesis, crystal and electronic structures, and one- and two-photon absorption properties of two quadrupolar fluorenyl-substituted tetraphenyl carbo-benzenes are described. These all-hydrocarbon chromophores, differing in the nature of the linkers between the fluorenyl substituents and the carbo-benzene core (C-C bonds for 3 a, C-C=C-C expanders for 3 b), exhibit quasi-superimposable one-photon absorption (1PA) spectra but different two-photon absorption (2PA) cross-sections σ2PA. Z-scan measurements (under NIR femtosecond excitation) indeed showed that the C≡C expansion results in an approximately twofold increase in the σ2PA value, from 336 to 656 GM (1 GM = 10(-50) cm(4) s molecule(-1) photon(-1)) at λ = 800 nm. The first excited states of Au and Ag symmetry accounting for 1PA and 2PA, respectively, were calculated at the TDDFT level of theory and used for sum-over-state estimations of σ2PA(λi), in which λi = 2 hc/Ei, h is Planck's constant, c is the speed of light, and Ei is the energy of the 2PA-allowed transition. The calculated σ2PA values of 227 GM at 687 nm for 3 a and 349 GM at 708 nm for 3 b are in agreement with the Z-scan results.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">26267308</PMID><DateCompleted><Year>2015</Year><Month>12</Month><Day>03</Day></DateCompleted><DateRevised><Year>2015</Year><Month>09</Month><Day>17</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3765</ISSN><JournalIssue CitedMedium="Internet"><Volume>21</Volume><Issue>40</Issue><PubDate><Year>2015</Year><Month>Sep</Month><Day>28</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Difluorenyl carbo-Benzenes: Synthesis, Electronic Structure, and Two-Photon Absorption Properties of Hydrocarbon Quadrupolar Chromophores.</ArticleTitle><Pagination><MedlinePgn>14186-95</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/chem.201500482</ELocationID><Abstract><AbstractText>The synthesis, crystal and electronic structures, and one- and two-photon absorption properties of two quadrupolar fluorenyl-substituted tetraphenyl carbo-benzenes are described. These all-hydrocarbon chromophores, differing in the nature of the linkers between the fluorenyl substituents and the carbo-benzene core (C-C bonds for 3 a, C-C=C-C expanders for 3 b), exhibit quasi-superimposable one-photon absorption (1PA) spectra but different two-photon absorption (2PA) cross-sections σ2PA. Z-scan measurements (under NIR femtosecond excitation) indeed showed that the C≡C expansion results in an approximately twofold increase in the σ2PA value, from 336 to 656 GM (1 GM = 10(-50) cm(4) s molecule(-1) photon(-1)) at λ = 800 nm. The first excited states of Au and Ag symmetry accounting for 1PA and 2PA, respectively, were calculated at the TDDFT level of theory and used for sum-over-state estimations of σ2PA(λi), in which λi = 2 hc/Ei, h is Planck's constant, c is the speed of light, and Ei is the energy of the 2PA-allowed transition. The calculated σ2PA values of 227 GM at 687 nm for 3 a and 349 GM at 708 nm for 3 b are in agreement with the Z-scan results.</AbstractText><CopyrightInformation>© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Baglai</LastName><ForeName>Iaroslav</ForeName><Initials>I</Initials><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France).</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse CEDEX 9 (France).</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Kiev National Taras Shevchenko University, 60 Volodymyrska Str., 01033 Kiev (Ukraine).</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>de Anda-Villa</LastName><ForeName>Manuel</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Barba-Barba</LastName><ForeName>Rodrigo M</ForeName><Initials>RM</Initials><AffiliationInfo><Affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Poidevin</LastName><ForeName>Corentin</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 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>Ramos-Ortíz</LastName><ForeName>Gabriel</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03. garamoso@cio.mx.</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, BP 44099, 31077 Toulouse CEDEX 4 (France). chauvin@lcc-toulouse.fr.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse CEDEX 9 (France). chauvin@lcc-toulouse.fr.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lepetit</LastName><ForeName>Christine</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 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>Saffon-Merceron</LastName><ForeName>Nathalie</ForeName><Initials>N</Initials><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse CEDEX 9 (France).</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Maldonado</LastName><ForeName>José-Luis</ForeName><Initials>JL</Initials><AffiliationInfo><Affiliation>Centro de Investigaciones en Óptica A.P. 1-948, 37000 León, Gto. (México), Fax: (+33) 5-61-55-30-03.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chauvin</LastName><ForeName>Remi</ForeName><Initials>R</Initials><AffiliationInfo><Affiliation>CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, BP 44099, 31077 Toulouse CEDEX 4 (France). valerie.maraval@lcc-toulouse.fr.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse CEDEX 9 (France). valerie.maraval@lcc-toulouse.fr.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>08</Month><Day>12</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">carbo-mers</Keyword><Keyword MajorTopicYN="N">charge transfer</Keyword><Keyword MajorTopicYN="N">chromophores</Keyword><Keyword MajorTopicYN="N">density functional calculations</Keyword><Keyword MajorTopicYN="N">nonlinear optics</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year><Month>02</Month><Day>05</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>8</Month><Day>13</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>8</Month><Day>13</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>8</Month><Day>13</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">26267308</ArticleId><ArticleId IdType="doi">10.1002/chem.201500482</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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