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>
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</affiliation>
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<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>
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<wicri:noCountry code="subField">31062 Toulouse CEDEX 9 (France)</wicri:noCountry>
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<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>
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<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>
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<Author ValidYN="Y"><LastName>de Anda-Villa</LastName>
<ForeName>Manuel</ForeName>
<Initials>M</Initials>
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<Author ValidYN="Y"><LastName>Barba-Barba</LastName>
<ForeName>Rodrigo M</ForeName>
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<Author ValidYN="Y"><LastName>Poidevin</LastName>
<ForeName>Corentin</ForeName>
<Initials>C</Initials>
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</AffiliationInfo>
<AffiliationInfo><Affiliation>Université de Toulouse, UPS, ICT-FR 2599, 31062 Toulouse CEDEX 9 (France).</Affiliation>
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<Author ValidYN="Y"><LastName>Ramos-Ortíz</LastName>
<ForeName>Gabriel</ForeName>
<Initials>G</Initials>
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</AffiliationInfo>
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<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>
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</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>
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<Author ValidYN="Y"><LastName>Maldonado</LastName>
<ForeName>José-Luis</ForeName>
<Initials>JL</Initials>
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</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>
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<Month>08</Month>
<Day>12</Day>
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<ISSNLinking>0947-6539</ISSNLinking>
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<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>
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