Abstract
Abstract Fluorescence solvatochromic shifts of 4,4′-diaminobiphenyl (DABP) were found to be less than those of 4-aminobiphenyl and the difference mainly occured in hydrogen bonding solvents. This shows that the net effect of hydrogen bonding interactions of two amino groups is less than that of one amino group. The unusual fluorescence red-shift observed for the monocation of DABP relative to the neutral form is not because of the amino group becoming more basic, but because of a large solvent relaxation in aqueous media. As the entire molecule becomes planar upon excitation, its behavior is found to be similar to that of 2,7-diaminofluorene in the S1 state. pKa values for various prototropic reactions in the S0 and S1 states were determined and are discussed.
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