Ultrafast excited state proton transfer dynamics of 1,2-dihydroquinolines in methanol solution

Abstract

Femtosecond and picosecond dynamics of 2,2,4,6-tetramethyl-1,2-dihydroquinoline (1) and 1,2,2,4,6-pentamethyl-1,2-dihydroquinoline (2) were studied in MeOH, MeOD, and Pr(i)OH to probe the early events of the photoinduced proton transfer (PT) between 1,2-dihydroquinolines (DHQ) and a solvent. From studies in the two solvents MeOH and Pr(i)OH and by examining the effect of deuterium replacement of proton, it has been established that PT takes 150-200 fs in MeOH, but does not occur in Pr(i)OH. The formation of PT products in the ground state proceeds concurrently to the relaxation of the higher vibrational excited singlet state to the thermally equilibrated state S(1) of DHQ. The absorption spectrum of the S(1) state was registered, and the time constant of its decay in MeOH (ca. 1 ns) agrees well with the lifetime of fluorescence measured recently by single photon counting.