Issue 17, 2011

Effects of alkoxy substitution on the crystal structure of 2,3-bis[(E)-4-(diethylamino)-2-alkoxybenzylideneamino]fumaronitrile derivatives

Abstract

The bisazomethine dyes derived from diaminomaleonitrile and aminobenzaldehydes, 2,3-bis[(E)-4-(dialkylamino)benzylideneamino]fumaronitrile derivatives, are known to have potential as dyes for forming J-aggregate vapour-deposited films, even though appropriate conditions for preparation of their pure J-aggregate films are unknown. In this study, an attempt was made to investigate the effects of alkoxy substitution on the crystal structures of eight bisazomethine dyes; our final goal was to obtain pure J-aggregates of bisazomethine dyes in a crystalline state. The focus of this study is on the relationship between changes in the molecular structure and the crystal structure, characterized by a two-dimensional molecular stacking layer and its alignment. We found that the interlayer distance between adjacent two-dimensional stacking layers can be controlled by alkoxy substitution, when the substituent chain length is less than C10, without any significant structural changes in the stacking layer. Our observation was confirmed by lattice energy calculations from an energetic perspective.

Graphical abstract: Effects of alkoxy substitution on the crystal structure of 2,3-bis[(E)-4-(diethylamino)-2-alkoxybenzylideneamino]fumaronitrile derivatives

Supplementary files

Article information

Article type
Paper
Submitted
12 Feb 2011
Accepted
24 May 2011
First published
04 Jul 2011

CrystEngComm, 2011,13, 5374-5383

Effects of alkoxy substitution on the crystal structure of 2,3-bis[(E)-4-(diethylamino)-2-alkoxybenzylideneamino]fumaronitrile derivatives

B. Kim, T. Jindo, R. Eto, Y. Shinohara, Y. Son, S. Kim and S. Matsumoto, CrystEngComm, 2011, 13, 5374 DOI: 10.1039/C1CE05198A

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