Click chemistry towards thermally reversible photochromic 4,5-bisthiazolyl-1,2,3-triazoles

Abstract

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.

Keywords

• aromatic stabilization energy
• diarylethene
• ruthenium(i) catalysed huisgen cyclization
• terarylene
• thermally reversible photochromism