Photoresponsive Organogel Based on Supramolecular Assembly of Tris(phenylisoxazolyl)benzene

Azobenzene-substituted tris(phenylisoxazolyl)benzene 1 was developed as a photoresponsive gelator. A detailed study of the self-assembly of the trans- and cis-isomers in solution revealed that the planar trans-isomer assembled to form molecular stacks along its C3 axis, whereas the cis-isomer did not owing to steric requirements. Based on diffusion ordered spectroscopy experiments, the size of the aggregates formed from the trans-isomer were roughly four times as large as those of the cis-isomer. The photoinduced gel-to-sol transition was achieved by irradiation with UV light at 360 nm. Solid-state morphologies of the trans- and cis-isomers were quite contrastive; the trans-isomer created fibrous supramolecular networks with a lot of voids in which solvent molecules could be immobilized, whereas the cis-isomer never created such fibrous morphologies. The trans–cis structural change of the azobenzene moieties obviously regulates the gelation ability of 1.