MersV1, Main, Exploration, bibRecord, 001C48

Functional carbo-butadienes: nonaromatic conjugation effects through a 14-carbon, 24-π-electron backbone.

Identifieur interne : 001C48 ( Main/Exploration ); précédent : 001C47; suivant : 001C49

Functional carbo-butadienes: nonaromatic conjugation effects through a 14-carbon, 24-π-electron backbone.

Auteurs : Arnaud Rives ; Valérie Maraval ; Nathalie Saffon-Merceron ; Remi Chauvin

Source :

Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2014.

RBID : pubmed:24311108

Abstract

A systematic study of carbo-butadiene motifs not embedded in an aromatic carbo-benzene ring is described. Dibutatrienylacetylene (DBA) targets R(1) C(R)CCC(Ph)C≡CC(Ph)CCC(R)R(2) are devised, in which R is C≡CSiiPr3 and R(1) and R(2) are R, H, or 4-X-C6 H4 , with the latter including three known representatives (X: H, NMe2 , or NH2 ). The synthesis method is based on the SnCl2 -mediated reduction of pentaynediols prepared by early or late divergent strategies; the latter allows access to a OMe-NO2 push-pull diaryl-DBA. If R(1) and R(2) are H, an over-reduced dialkynylbutatriene (DAB) with two allenyl caps was isolated instead of the unsubstituted DBA. If R(1) =R(2) =R, the tetraalkynyl-DBA target was obtained, along with an over-reduced DBA product with a 12-membered 1,2-alkylidene-1H2 ,2H2 -carbo-cyclobutadiene ring. X-ray crystallography shows that all of the acyclic DBAs adopt a planar trans-transoid-trans configuration. The maximum UV/Vis absorption wavelength is found to vary consistently with the overall π-conjugation extent and, more intriguingly, with the π-donor character of the aryl X substituents, which varies consistently with the first (reversible) reduction potential and first (irreversible) oxidation peak, as determined by voltammetry.

DOI: 10.1002/chem.201303169
PubMed: 24311108

Affiliations:

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<front><div type="abstract" xml:lang="en">A systematic study of carbo-butadiene motifs not embedded in an aromatic carbo-benzene ring is described. Dibutatrienylacetylene (DBA) targets R(1) C(R)CCC(Ph)C≡CC(Ph)CCC(R)R(2) are devised, in which R is C≡CSiiPr3 and R(1) and R(2) are R, H, or 4-X-C6 H4 , with the latter including three known representatives (X: H, NMe2 , or NH2 ). The synthesis method is based on the SnCl2 -mediated reduction of pentaynediols prepared by early or late divergent strategies; the latter allows access to a OMe-NO2 push-pull diaryl-DBA. If R(1) and R(2) are H, an over-reduced dialkynylbutatriene (DAB) with two allenyl caps was isolated instead of the unsubstituted DBA. If R(1) =R(2) =R, the tetraalkynyl-DBA target was obtained, along with an over-reduced DBA product with a 12-membered 1,2-alkylidene-1H2 ,2H2 -carbo-cyclobutadiene ring. X-ray crystallography shows that all of the acyclic DBAs adopt a planar trans-transoid-trans configuration. The maximum UV/Vis absorption wavelength is found to vary consistently with the overall π-conjugation extent and, more intriguingly, with the π-donor character of the aryl X substituents, which varies consistently with the first (reversible) reduction potential and first (irreversible) oxidation peak, as determined by voltammetry. </div>
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Functional carbo-butadienes: nonaromatic conjugation effects through a 14-carbon, 24-π-electron backbone.

Functional carbo-butadienes: nonaromatic conjugation effects through a 14-carbon, 24-π-electron backbone.

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Abstract

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