SYNTHESES OF AMPHIPHILIC PHOTOCHROMIC COMPOUNDS AND THEIR PHOTOCHROMISM IN LANGMUIR-BLODGETT-FILMS

Amphiphilic spiropyrans and fulgides for Langmuir-Blodgett (LB) films were prepared, and their photochromism was studied. 8-Methoxy-6-nitro-r-petadeeylspiropyran 4a, 6-methoxy-8-nitro-r-octadeeylspiropyran 4b, S-docosanoyloxymethyl-G-nitro-l'-octadecylspiropyran 4 c, and their derivatives, amphiphilic Nitrospitopyrans 5a-c and bromspiropyrans 6b-c, were synthesized. Amphiphilic furylfulgides 9 a-c having a long alkyl chain on furan ring, apposition of the side chain, and on N-position of a nitrogen analog were also synthesized. An amphiphilic thienyl-substituted fulgide was synthesized by a similar procedure. Those compounds underwent photochromic reaction in LB film as similar as in solutions. The colored forms of spiropyran 4a, 4c and 6e in LB film were found to form J-aggregation. LB films of fulgides showed thermal decomposition reaction by the ring opening at the anhydride part. © 1990, The Chemical Society of Japan. All rights reserved.