A. Spalletti et al., Spectral characterization, photophysics, and photochemistry of the four stereoisomers of 1-(2-anthryl)-4-phenyl-1,3-butadiene, J PHYS CH A, 103(45), 1999, pp. 8994-9002
Using a synthetic strategy, based on retention of stereochemistry in the re
agent cinnamaldehyde, the four geometrical isomers of 1-(2-anthryl)-4-pheny
l-1,3-butadiene were obtained and chromatographically purified. Their struc
tures were established by optical and nuclear magnetic spectrometry and con
firmed by their photochemical behavior. Their excited state properties were
investigated by stationary and pulsed fluorimetric techniques and by laser
Bash photolysis. This paper reports the spectral characterization of the f
our isomers and the photophysical and photochemical parameters obtained by
irradiation in a nonpolar solvent at different temperatures. The important
contribution of adiabatic pathways in the photoisomerization mechanism and
the role of an upper excited singlet state in the relaxation properties are
discussed. Indication of the presence of at least two conformers was obtai
ned only when exciting at the extreme red onset region of the absorption sp
ectrum.