ISSN:
0947-3440
Keywords:
Thermal and photochemical electrocyclization reactions
;
Photochromism
;
Molecular switching
;
Luminescent properties
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199509227