Insights into a novel class of azobenzenes incorporating 4,6-O-protected sugars as photo-responsive organogelators

Abstract

A novel class of 4,6-O-butylidene/ethylidene/benzylidene β-D-glucopyranose gelator functionalized with photo-responsive azobenzene moieties were designed and synthesized and also characterized using different spectral techniques. These azobenzene-based organogelators can gel even at lower concentrations (critical gelation concentration – 0.5% and 1%). A morphological study of the gels shows one-dimensional aggregated bundles and helical fibres. The main driving force for the self-assembly is through cooperative interactions exhibited by the different groups viz., sugar hydroxyl (hydrogen bonding interaction), azobenzene (aromatic π–π interaction) and alkyl chain of the protecting group (van der Waals interaction).