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

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 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. [ABSTRACT FROM AUTHOR]