Spectroscopy and photophysics of monoazaphenanthrenes I. Absorption and fluorescence spectra of phenanthridine and 7,8-benzoquinoline

The absorption and fluorescence spectra of phenaentridine and 7,8-benzoquinoline have been measured in liquid solutions of non-polar, aprotic hydrocarbon solvents (n-hexane and cyclohexane) and in strongly polar (and hydrogen-bonding) methanol. The analysis of the Stokes' shift between absorption and fluorescence spectra has shown that for both molecules the observed solvent effects on their absorption and fluorescence spectra can be described in terms of universal solvent-solute interactions (no evidence of specific solvent-solute interactions, of the type of hydrogen bond formation with participation of lone-pair electrons of nitrogen atom, has been found). On the other hand, the measured decay time profiles of fluorescence are visibly longer in methanol solution than in non-polar, aprotic solvents and these observations are consistent with the observed increase in fluorescence intensity of both molecules in strongly polar methanol solution. The radiative lifetimes of the first excited singlet state do not differ noticeably for both molecules, but it has turned out that in the case of phenanthridine the nonradiative processes are getting less effective in methanol solution than in the case of 7,8-benzoquinoline, which can presumably be related to the role of different position of the substitution of nitrogen atom in these two molecules.