The fluorescence properties of hypocrellin B and its amino-substituted derivative: photoinduced intramolecular proton transfer and photoinduced intramolecular electron transfer.

Abstract

We report on the emission spectra and emission quantum yields of a newly synthesized hypocrellin dye, 2-demethoxy-2,3-ethylenediamino hypocrellin B (EDAHB), and its parent HB in different solvents of varying polarity. Our results demonstrate that EDAHB is one of the few dyes that exhibit highly solvent polarity-dependent fluorescence in the useful region (680-730 nm). Therefore, it offers some applications in the biomedical field as a fluorescent probe molecule. The solvatochromic effect of EDAHB is proposed to be due to a distinct change in the dipole moment of the dye on excitation. A photoinduced intramolecular proton transfer and a photoinduced intramolecular electron transfer process are considered relevant for the fluorescence properties of HB and EDAHB, respectively.