Development of highly fluorescent photochromic material with high fatigue resistance

Efficient and reversible fluorescence modulation with excellent photo-stability was achieved from a sulfone form of diacetyl diarylethene, 1,2-bis(6-acetyl-2-methyl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentene (DABTFO4). The DABTFO4 emits strong fluorescence in the closed-ring isomer even in the absence of extra fluorophores. The fluorescence quantum yield, fatigue resistance, and photo-cyclization yield of DABTFO4 were significantly improved compared with the unsubstituted 1,2-bis(2-methyl-1-benzothiophene-1, 1-dioxide-3-yl)perfluorocyclopentene (BTFO4) and the sulfide analogue, 1,2-bis(6-acetyl-2-methyl-l-benzothiophene-3-yl)perfluorocyclopentene (DABTF6). (c) 2006 Elsevier Ltd. All rights reserved.