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

Abstract

Three new photochromic compounds, 3-(2,5-dimethyl-3-thienyl)-4-(2-phenyl-5-methyl-4-thiazolyl)-1,8-napht-were synthesized and their photochromic properties were studied. Compound 1-O was synthesized by two consecutive Suzuki coupling reactions using 2,5dimethylthiophene-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 (or light yellow) to blue-green, purple, or orange colors (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 (or light yellow) solution by exposure to visible light at 530 nm.

Investigation of Photochromic Fluorescence Features and Synthesis of Diarylethene Type Naphthalimide Compounds

“…Photochromic fluorescent diarylethenes have attracted attention in the development and use of possible opticalelectronic devices in recent years as molecular switches and optical memory systems (1)(2)(3)(4)(5)(6).…”

Fluorescent photochromic complex of 1,8-naphthalimide derivative and benzopyrane containing benzo-18-crown-6 ether

“…19 A series of naphthalimides containing dithienylethene fragments in different position of fluorophore molecules was synthesized and their photochromic properties were studied. [20][21][22] When thienyl fragments are in the 3 rd and 4 th positions of the naphthalene ring of the naphthalimide derivative, the photochromic conversion to the cyclic form does not affect the fluorescence characteristics of naphthlimide. 20 In the next research, the two prepared photochromic bisthienylethene derivatives with a six-membered aryl ring of the fluorescent naphthalimide moiety as the center ethene bridging unit differ from the previous one by OMe group in thienyl heterocycles.…”

“…[20][21][22] When thienyl fragments are in the 3 rd and 4 th positions of the naphthalene ring of the naphthalimide derivative, the photochromic conversion to the cyclic form does not affect the fluorescence characteristics of naphthlimide. 20 In the next research, the two prepared photochromic bisthienylethene derivatives with a six-membered aryl ring of the fluorescent naphthalimide moiety as the center ethene bridging unit differ from the previous one by OMe group in thienyl heterocycles. 21 They exhibit considerably high cyclization quantum yield and good fatigue resistance.…”