Synthesis, structures and properties of two donor-acceptor acridone-based compounds.

Abstract

Two donor-acceptor acridone-based compounds, namely, 2-{10-[4-(diphenylamino)phenyl]acridin-9-ylidene}malononitrile (TPA-AD-DCN), C34H22N4, and 2-{10-[4-(9H-carbazol-9-yl)phenyl]acridin-9-ylidene}malononitrile (CzPh-AD-DCN), C34H20N4, have been synthesized in high yield and their structures determined. TPA-AD-DCN and CzPh-AD-DCN crystallized in the centrosymmetric space groups P\overline{1} and P21/c, respectively. Both molecules adopt a `butterfly-like' configuration of the common part of the structure and differences occur within the substituents on the acridine N atom. A Hirshfeld surface analysis showed that the H...H and C...H/H...C contacts constitute a high percentage of the intermolecular interactions. The optical and electrochemical properties, as well as theoretical calculations, of TPA-AD-DCN and CzPh-AD-DCN support the structural characterization of these materials. As crystallization-induced emission materials, TPA-AD-DCN and CzPh-AD-DCN are anticipated to be of potential use in the construction of promising optoelectronic materials.