Synthesis, Electronic Properties, and Electrochemiluminescence of Donor-Substituted Phenylethynylanthronitriles

A new series of π-conjugated donor−acceptor compounds (1−6) with inherent redox centers have
been prepared and studied with respect to their electronic properties. The photophysical
characteristics of these compounds have been studied in relation to their structures. Cyclic
voltammetry and UV−vis spectroelectrochemistry were used to probe the ground-state electronic
properties of the neutral and charged species. The observed electronic absorption properties of the
neutral and charged molecules are explained with the help of frontier orbital structures and
electrostatic potential maps obtained from density functional theory (DFT, B3LYP/6-31G*)
calculations. Electrochemiluminescence (ECL) of this series of donor-substituted phenylethynylanthronitriles with different donors was also studied. The structure−property relationship of all
of the compounds is discussed.