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Functional dyes for molecular switching . Dihydroazulene/vinylheptafulvene photochromism: Effect of π‐arylenes on the switching behavior
Author(s) -
Spreitzer Hubert,
Daub Jörg
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199509227
Subject(s) - photochromism , chemistry , molecular switch , chromophore , fluorescence , photochemistry , luminescence , kinetics , covalent bond , optical switch , cycloaddition , sequence (biology) , optoelectronics , organic chemistry , molecule , materials science , physics , quantum mechanics , biochemistry , catalysis
The reversible interconversion of dihydroazulene (DHA) and vinylheptafulvene (VHF) can be utilized to switch a number of physical properties. This communication reports on a fluorescent switch. By a multistep sequence involving an [8 + 2] cycloaddition route 9‐anthracenyl‐1,4‐phenylene was covalently attached to C‐2 of the DHA chromophore affording DHA‐1 which undergoes complete and clean photochemical ring opening to vinylheptafulvene VHF‐1 . The latter is thermally reverted to DHA‐1 . The kinetics and the energetics of the thermal back reaction are discussed. On/off switching of luminescence was investigated: DHA‐1 displays fluorescence whereas VHF‐1 is nonfluorescent at ambient temperature.