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Comparison of CC triple and double bonds as spacers in push-pull chromophores

Frank, BB, Laporta, PR, Breiten, B, Kuzyk, MC, Jarowski, PD, Schweizer, WB, Seiler, P, Biaggio, I, Boudon, C, Gisselbrecht, J-P and Diederich, F (2011) Comparison of CC triple and double bonds as spacers in push-pull chromophores European Journal of Organic Chemistry, 2011 (23). pp. 4307-4317.

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Abstract

We report the synthesis and properties of two series of homologous donor–acceptor (D–A) chromophores in which N,N-dimethylanilino (DMA) or N,N-dihexylanilino (DHA) donors and dicyanovinyl acceptors are separated by up to four C≡C triple-bond spacers or up to three C=C double-bond spacers. The intramolecular charge-transfer (CT) interactions of the new D–A oligoynes and the known all-trans D–A oligoenes were investigated by X-ray crystallography, electrochemistry, UV/Vis spectroscopy, and theoretical calculations. In both series, the optical and electrochemical HOMO–LUMO gaps decrease with increasing spacer length. The HOMO–LUMO gaps for the D–A oligoynes and oligoenes with a given spacer length are nearly identical. The effect of the spacer length was found to level-off for spacers with more than six carbon atoms. The third-order optical nonlinearity of both series of molecules was determined by measuring the rotational averages of the third-order polarizabilities rot by degenerate four-wave mixing.

Item Type: Article
Authors :
NameEmailORCID
Frank, BBUNSPECIFIEDUNSPECIFIED
Laporta, PRUNSPECIFIEDUNSPECIFIED
Breiten, BUNSPECIFIEDUNSPECIFIED
Kuzyk, MCUNSPECIFIEDUNSPECIFIED
Jarowski, PDUNSPECIFIEDUNSPECIFIED
Schweizer, WBUNSPECIFIEDUNSPECIFIED
Seiler, PUNSPECIFIEDUNSPECIFIED
Biaggio, IUNSPECIFIEDUNSPECIFIED
Boudon, CUNSPECIFIEDUNSPECIFIED
Gisselbrecht, J-PUNSPECIFIEDUNSPECIFIED
Diederich, FUNSPECIFIEDUNSPECIFIED
Date : 2011
Identification Number : 10.1002/ejoc.201100378
Depositing User : Symplectic Elements
Date Deposited : 28 Mar 2017 13:10
Last Modified : 31 Oct 2017 16:47
URI: http://epubs.surrey.ac.uk/id/eprint/805650

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