Fluorescence and photocycl1zation of N-naphthyl-substituted pyridinium cations

Autor: Tymyanskii, Ya. R., Feingel'man, V. M., Knyazhanskii, M. I., Kholodova, N. V.
Zdroj: Chemistry of Heterocyclic Compounds; November 1984, Vol. 20 Issue: 11 p1262-1266, 5p
Abstrakt: The spectral-fluorescent and photochemical properties of 1-naphthyl-2,4-di- and 2,4,6-triphenylpyridinium perchlorates were investigated in solutions at 293 and 77 °K. The anomalously large Stokes shift of the fluorescence was due to the adiabatic change in the structure of the molecules as a result of rotations of the C- or N-aryl substituents. The observed phosphorescence arises as a result of intramolecular T-T transfer of energy to the N-naphthyl radical. 1-Naphthyl-2,4-diphenylpyridinium cations are capable of photocyclization with the formation of intensely fluorescent derivatives of benzo[b or c]pyrldo[1,2-f]phenanthridinium, isolated with high yields in preparative photolysis.
Databáze: Supplemental Index