The synthesis and photochemical properties of amphiphilic phenylazonaphthalenes

Abstract

Three novel amphiphilic phenylazonaphthalenes, namely, 6-(4-(4-octylphenylazo)naphthoxy)hexanoic acid, 6-(4-(4-dodecylphenylazo)naphthoxy)hexanoic acid, 6-(4-(4-hexadecylphenylazo)naphthoxy)hexanoic acid, were synthesized by diazo coupling, etherification and hydrolysis reactions successively. The kinetic studies of the trans–cis isomerization indicated that about 95% of the trans isomers of these compounds in chloroform solutions were transformed to cis isomers under the irradiation of near-ultraviolet light (380±30 nm) observed from UV–Vis spectra. In the dark condition, the cis isomers could reversibly convert to trans isomers following the first-order kinetics at the rates of 4.9×10^-4, 5.7×10^-4, 7.7×10^-4 S^-1, respectively.