Carbo-biphenyls and Carbo-terphenyls: Oligo(phenylene ethynylene) Ring Carbo-mers.
Identifieur interne : 001D48 ( Ncbi/Curation ); précédent : 001D47; suivant : 001D49Carbo-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
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<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>
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