Dual fluorescence in a Schiff base derived from an acridinedione dye. excited state intramolecular proton transfer

Newly synthesized nonconjugated, but covalently linked, bichromophoric systems (ADDSA) contain a salicylideneaniline (SA) moiety linked to an acridinedione (ADD) fluorophore via a covalent bond. The absorption and fluorescence characteristics of the ADDSA systems in various solvents reveal that the dual fluorescence originates from two different chromophores in the same molecule. The solvent polarity independent, long wavelength anomalous emission originates from the keto form of SA moiety via excited state intramolecular proton transfer (ESIPT). The ESIPT pathway was further confirmed by the benzylideneaniline (BA) and ADD moieties coupled non-proton transfer model system (ADDBA). Absence of the longer wavelength anomalous emission in the steady state as well as the shorter lifetime component in the time-resolved study for ADDBA system supports ESIPT mechanism for long wavelength anomalous emission in ADDSA system.