The synthesis of new 3,4-(bisaryl)-1,8-naphthalimide and 2,3-(bisaryl)-7 H -benzimidazo[2,1-a]benzo[d]isoquinolin-7-one compounds and an investigation of their photochromic properties

Authors : Ersin ORHAN, Mahmut KÖSE, Tolga YAZAN

Pages : 1086-1094

View : 15 | Download : 7

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :  Three new photochromic compounds, 3-insert ignore into journalissuearticles values(2,5-dimethyl-3-thienyl);-4-insert ignore into journalissuearticles values(2-phenyl-5-methyl-4-thiazolyl);-1,8-napht- halimide insert ignore into journalissuearticles values(1-O);, 2,3-bisinsert ignore into journalissuearticles values(2-phenyl-5-methyl-4-thiazolyl);-7 H H H H H -benzimidazo[2,1-a]benzo[de]isoquinolin-7-one insert ignore into journalissuearticles values(2-O);, and 2,5-dimethyl-3-thienyl);-7 H H -benzimidazo[2,1-a]benzo[de]isoquinolin-7-one insert ignore into journalissuearticles values(3-O);, were synthesized and their photochromic properties were studied. Compound 1-O was synthesized by two consecutive Suzuki coupling reactions using 2,5-dimethylthiophene-3-boronic acid and 5-methyl-2-phenylthiazole-4-boronic acid. Photochromic compounds 2-O and 3-O were prepared by multistep reactions starting with 3-iodo-4-bromo-1,8-naphthalic anhydride and 2,5-dimethylthiophene-3-boronic acid or 2-phenyl-5-methylthiazole-4-boronic acid. All photochromic compounds showed a color change from colorless insert ignore into journalissuearticles values(or light yellow); to blue-green, purple, or orange colors insert ignore into journalissuearticles values(depending on the nature of the structures); on exposure to UV light at 365 nm in ethyl acetate solutions. The colored solutions can be reversed to the original colorless insert ignore into journalissuearticles values(or light yellow); solution by exposure to visible light at 530 nm.
Keywords : Diarylethene, photochromism, 1, 8 naphthalimide, 8 naphthalic anhydride, 7 H benzimidazo, 2, 1 a, benz, de, isoquinolin 7 one