Access to a Phthalazine Derivative Through an Angular -Quinacridone.

Intramolecular electrophilic cyclization of a bisanthranilate afforded an angular -quinacridone compound, which condensed with hydrazine to give a phthalazine derivative. A [2+2+2] cyclization reaction occurred at the C-N double bond position of phthalazine when reacted with dimethyl acetylenedicarboxylate. The structures of these novel compounds were confirmed by crystallographic analysis.

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

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.