On the Relationship between Molecular Geometry and Excited-State Properties of 9-Anthrylalkenes

Article abstract of DOI:10.1021/jo00172a020

The excited-state properties of a series of 1-substituted and 1,1-disubstituted 2-(9-anthryl)alkenes have been investigated in terms of their fluorescence spectra and photochemical isomerizations.Large Stokes shifts of up to 10000 cm^-1 between absorption and emission maxima are attributed to geometrical differences between the ground state and the emitting excited state.The : ratio of the photostationary state was found to depend markedly on the nature of the 1-substituent.Photochemical isomerization of 1,3- and 1,5-bis(9-anthryl)-substituted trans olefins results in the formation of intramolecular <4? + 4?> or <4? + 2?> cycloaddition products.The cycloaddition reactions of carbonyl-substituted anthracenes are suggested to involve the triplet excited state.