N-Substitution of acridone with electron-donating groups: crystal packing, intramolecular charge transfer and tuneable aggregation induced emission

Abstract

Acridone derivatives with electron-rich triphenylamine functionalized at the amino position were synthesized and their properties were experimentally and computationally investigated. The single crystal structure analysis revealed that the π–π interaction of acridone and the formation of hydrogen bonds of carbonyl and the hydrogen atoms of the pending phenyl ring were crucial in the determination of molecular packing in the crystalline state. An intramolecular charge transfer (ICT) process was observed between acridone and triphenylamine even with reduced conjugation by the nitrogen atom of acridone. Tuneable aggregation induced emissions with blue and green fluorescence were found due to the different aggregation state and particle size, which varied according to the water content in THF. Furthermore, the size of the spacer between acridone and the appended amine was also important in adjusting the property of aggregation induced emission or aggregation caused quenching in the solid state.