Synthesis and photochromism of catechol-containing symmetrical azobenzene compounds

Abstract

Symmetrical azobenzene derivatives with two catechol groups, 1d–4d, were synthesized as kinds of novel compounds, and the structures were confirmed using mass spectrometry and nuclear magnetic resonance spectroscopy. These compounds could attain photostationary state rapidly in solution upon UV irradiation, and their photochromism had good reversibility. Substituents and their positions on azobenzene chromophore had obvious influence on the maximum absorption and photochromic performances of these as-synthesized compounds. Electron-donating group on ortho positions could contribute to the redshift π–π* band. The sulfonamide group that is bonded to dopamine molecules and azobenzene rings caused a negligible n–π* transition of cis isomer, resulting in photobleaching upon UV irradiation. Among the four compounds, 4d had the strongest electron-donating ortho -methoxy substituents and lower planarity; thus its absorption could decrease more significantly upon UV irradiation of the same intensity, and its cis -to- trans conversion could be up to 63%. Furthermore, owing to the presence of catechol groups, 4d showed an effective affinity and adhesion to substrate, and on the surface of substrate, a weak colour change could be observed upon UV irradiation, but the reversibility was poorer than that in solution.