Bisarylindenones and an acetal derivative, a novel thermally irreversible photochromic family based on 6pi-electrocyclization with three easily modifiable functional groups, have been synthesized. 2,3-Bis(5-methyl-2-phenyl-4-thiazolyl)indenone showed photochromic back-and-forth reactions with two different visible lights. Its ethylene acetal recorded 0.81 as the photocyclization quantum yield in hexane, which is the largest value known to date for 6pi-electrocyclization in solution.
Three new diarylethenes were synthesized from 1,2-bis(5-methyl-2-(4-substituted-phenyl)thiazol-4-yl)ethyne and benzyl azide through Ru(I)-catalyzed Huisgen cyclization reactions. The 4,5-bisthiazolyl-1,2,3-triazoles thus prepared, which belong to the terarylene family, showed thermally reversible photochromism. The absorption maximum wavelengths of the closed forms are longer than other terarylenes reported so far. The thermal back reactions are much faster when the substituents on the terminal phenyl groups are electron-withdrawing cyano groups than when they are electron-donating methoxy groups.
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