Chiral Amplification of the Structure and Viscoelasticity of a Supramolecular Polymeric System Consisting of N,N‘,N‘‘-Tris(3,7-Dimethyloctyl)Benzene-1,3,5-Tricarboxamide and n-Decane

Abstract

The influence of a chiral gelator molecule, N,N‘,N‘‘-tris-(S)-(3,7-dimethyloctyl)benzene-1,3,5-tricarboxamide ((S)DO3B), on the structure in the formation of supramolecular polymers and viscoelasticity was examined in an organogel system consisting of a racemic mixture of the gelator molecule, N,N‘,N‘‘-tris(3,7-dimethyloctyl)benzene-1,3,5-tricarboxamide (DO3B), and n-decane. In the absence of the chiral gelator, equal amounts were observed of the right- and left-handed helicities of the formed columnar supramolecular polymers. Addition of (S)DO3B markedly induced one helicity in excess, due to the Majority Rule effect. Although there are two possibilities, (1) left- and right-handled helices within single supramolecular polymers and (2) mixtures of homochiral supramolecular helical polymers, the viscoelasticity of the system supports the former. Without (S)DO3B, 60% of the amide groups of the gelators formed hydrogen bonding in the system; upon increasing the relative (S)DO3B composition (relative to the ...