Donor-substituted phenyl-π-chromones: electrochemiluminescence and intriguing electronic properties

Abstract

Phenylethynylchromones bearing different donor groups at the phenyl moiety have been prepared and their photophysical and electrogenerated chemiluminescence (ECL) properties have been studied with respect to their structural features. Intriguingly, the presence and variation of donor groups do not much influence the absorption spectra, which can be compared with the spectrum of unsubstituted chromone, whereas the photoluminescence (PL) spectra show pronounced changes. Density functional theory (DFT) calculations indicate enhancement of HOMO energy levels upon increasing the donor strength. The photophysical properties have also been studied in various solvents, and the PL spectra in particular show the anticipated trend. The introduction of π-extension imparts ECL to the new molecules and the electronic coupling between the donor and the acceptor moieties through C–C triple bond influences ECL emission maxima. Weaker donors impart excimer ECL while stronger donors impart monomeric intramolecular charge transfer (ICT) ECL.