Diarylmaleic anhydrides: unusual organic luminescence, multi-stimuli response and photochromism

Abstract

Diarylmaleic anhydride derivatives containing benzene (BPMA), thiophene (BTMA) and indole (BIMA) exhibit diverse and distinct fluorescence: aggregation-caused quenching (ACQ) of red emission of BIMA, blue aggregation-induced emission (AIE) of BPMA, and green dual-state emission (DSE) of BTMA in both solution and the solid state. Theoretical calculation and crystal structure analysis indicate that intramolecular and intermolecular interactions are responsible for their different emission behavior. A series of DSE-active molecules with full-color emission could be developed for the first time, through modification of the structures of BPMA and BIMA. Interestingly, BTMA and BPMA display multi-stimuli-responsive luminescence with a high-contrast (Δλ_em > 100 nm) and an unusual photochromic phenomenon in dichloromethane, which were utilized to construct rewritable data storage and mimic molecular logic operation (4-to-2 encoder and 1 : 2 demultiplexer), respectively.