Influence of inter- and intramolecular H-bonding on the mesomorphic and photoswitching behaviour of (E)-4-((4-(hexyloxy)phenyl)diazenyl)-N-phenyl benzamides

Abstract

We report on the synthesis, phase behaviour and photoswitching studies of new azo linked rod-shaped molecules. These novel materials consist of three phenyl rings separated by a diazo, amide linkage with a hexyloxy tail and 2,4-substituents at either end of the phenyl ring. The mesomorphic behaviours, phase transition temperature including the enthalpies were characterized by polarizing optical microscope (POM) and differential scanning calorimetry (DSC). The influence of inter- and intramolecular hydrogen bonding on mesomorphic and photoisomerization was studied. Photoisomerization studies carried out both in the solid and liquid phase show the quick E–Z transition with prolonged thermal back relaxation (Z–E) by using UV-Visible spectroscopy. This interesting behaviour could be attributed to the presence of the hexyloxy tail, lateral electron withdrawing group and the influence of inter- or intramolecular hydrogen bonding. Excellent bright and dark states were accomplished using one of these materials in optical storage device. Further tuning is necessary to employ them for real applications.