Tunable Aggregation-induced Emission and Emission Colors of Imidazolium and Pyridinium Based Hydrazones

Aggregation-induced emission (AIE) materials have drawn great attention for their wide applications as optical materials. The applications of AIE materials, however, are restricted by the complicated syntheses, hydrophobic properties and short emission wavelengths. Herein, an imidazolium based hydrazone ( E )-1-(4-methoxyphenyl)-2-((1-methyl-1H-imidazol-2-yl)methylene)hydrazine hydrochloride ( 1 ) and a pyridinium based hydrazone ( E)- 1-(4-methoxyphenyl)-2-(pyridin-4-ylmethylene)hydrazine hydrochloride ( 2 ) have been synthesized. Notably, 1 and 2 in crystals show distinct green and near-infrared (NIR) fluorescence, with emission peaks at 530 and 688 nm, and Stokes shifts of 176 and 308 nm, respectively. After grinding the crystals to powder, the absolute fluorescence quantum yield ( Φ F ) of 1 is increased from 4.2% to 10.6%, and the Φ F of 2 is increased from 0.2% to 0.7%. X-ray crystallography studies together with theoretical calculations indicate that the enhanced emission of 1 arises from hydrogen bonding induced rigid network, and the fluorescence in the NIR region and large Stokes shift of 2 are attributed to its twisted molecular structure and strong push–pull effect. Graphical Abstract