Self-assembly of photochromic diarylethenes with amphiphilic side chains: reversible thermal and photochemical control

Diarylethene derivatives with hexaethylene glycol side chains were synthesized and their self-assembling and photochromic reactivity were investigated. The diarylethenes showed photochromism in organic solvents and even in water. The aqueous solution of the compounds turned turbid quickly upon heating. The clouding behavior was investigated using H-1 NMR spectroscopy, dynamic light scattering, and absorption spectroscopy. It was revealed that, in the aqueous solution, the compounds self-assembled into aggregates, and the aggregates were loosened by raising the temperature. The cloud-point temperature of the closed-ring isomer was 5-7 degrees C lower than that of the open-ring isomer. When asymmetric methyl groups were introduced in the amphiphilic side chains, induced circular dichroism (ICD) was observed upon irradiation with UV light in water. This ICD was explained by the difference in the self-assembling behavior between the open- and the closed-ring isomers. It was suggested that the closed-ring isomers assembled into a chiral nanostructure.