Physicochemical Properties of Derivatives of N, N-Dimethylamino-cyclic-chalcones: Experimental and Theoretical Study

摘要

A series of three N, N-dimethyl-amino-cyclic-chalcones chromophores of the D-p-A type (1-3) where, (Donor= N, N-dimethylaniline) and Acceptor= indan-1-one (1), 3,4-dihydro-2H-naphthalen-1-one (2) and 3,4,5-tetrahydro-benzocyclohepten-1one (3), were synthesized and their structural, optical and electronic properties were studied. The influence of fused cycling ring size on their properties was investigated using cyclic voltammetry, steady-state absorption, steady-state fluorescence and DFT theoretical calculations. Both experimental and theo-retical calculations have been used to explain the observed structural, energetic and spectral differences in these compounds. These compounds have almost similar E-(OX) (1/2.) However, the measured E-(Red) (1/2) vary. The fused cyclic ring has more impact on the HOMO energies than LUMO's. Protonation could be facilitated on two sites. However, our DFT and TD-DFT calculations reveal that carbonyl oxygen has the most-negative-surface electrostatic potential, thus the highest affinity toward accepting H+.