Conformational analysis of 1,3-benzenediol dibenzoate as a model of banana-shaped molecules forming chiral smectic phases

Banana-shaped molecules, e.g. 1,3-phenylene bis[4-(4-n-alkoxyphenyliminomethyl)benzoates] and 1,3-phenylene bis[4-(4-n-alkylphenyliminomethyl)benzoates], form ferroelectric and chiral smectic phases without a chiral carbon. C-13 NMR measurement suggested that 1,3-benzenediol dibenzoate (BD) moiety assumes asymmetrically twisted conformation which may be ascribed to the chirality of the phases. In this study, conformational analysis was carried out for ED by using the density functional theory (DFT) calculation. The results indicated that the asymmetrical twist conformation of the ED moiety is most stable. (C) 2001 Elsevier Science B.V. All rights reserved.