Supramolecular liquid crystals formed by hydrogen bonding between a benzocrown-bearing stilbazole and carboxylic acids

The mesomorphism of hydrogen bonded complexes formed between 4'-carboxybenzo-15-crown-5 stilbazolyl ester (CBCSE) as proton acceptor and carboxylic acids as proton donors is discussed. CBCSE is a monotropic mesogen, forming a nematic phase upon quench cooling. A total of 32 hydrogen bonded complexes has been studied. Hydrogen bonding with carboxylic acids stabilizes the nematic phase, and/or induces a smectic A (SmA) phase. CBCSE forms 1:1 complexes (molar ratio) with alkanoic acids (fatty acids) and 2:1 complexes with alkanedioic acids. None of these proton donors is a mesogen itself, but the hydrogen bonded complexes are. The influence of the chain or spacer length on the transition temperatures is discussed. Besides the homologous series of the alkanoic and alkanedioic acids, the following carboxylic acids were used in this study: diglycolic acid, pyridine-2,6-dicarboxylic acid, 4-dodecyloxybenzoic acid, 3,4-bis(dodecyloxy)benzoic acid, 2,3,4-tris(dodecyloxy)benzoic acid and 3,4,5-tris(dodecyloxy)benzoic acid, phthalic acid, isophthalic acid and terephthalic acid.