The synthesis and photochemical properties of amphiphilic phenylazonaphthalenes

Three novel amphiphilic phenylazonaphthalenes, namely, 6-(4-(4-octylphenyla zo)naphthoxy)hexanoic acid, 6-(4-(4-dodecylphenylazo)naphthoxy)hexanoic aci d, 6-(4-(4-hexadecylphenylazo)naphthoxy)hexanoic acid, were synthesized by diazo coupling, etherification and hydrolysis reactions successively. The k inetic studies of the trans-cis isomerization indicated that about 95% of t he trans isomers of these compounds in chloroform solutions were transforme d to cis isomers under the irradiation of near-ultraviolet light (380 +/- 3 0 nm) observed from UV-Vis spectra. In the dark condition, the cis isomers could reversibly convert to trans isomers following the first-order kinetic s at the rates of 4.9 x 10(-4), 5.7 x 10(-4), 7.7 x 10(-4) S-1, respectivel y. (C) 1998 Elsevier Science Limited. All rights reserved.