Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties.

Novel pyridine-based fluorescing compounds, viz. pyrido[1,2- a ]pyrrolo[3,4- d ]pyrimidines 3a , b and N -methyl-4-((pyridin-2-yl)amino)maleimides 4a - e , were selectively prepared by a one-pot reaction between a functionalized maleimide and 2-aminopyridines with electron-donating or electron-withdrawing groups at position 5 and were investigated photophysically and computationally. The photophysical studies revealed that all the synthesized compounds exhibited fluorescence in organic solvents, while N -methyl-4-((pyridin-2-yl)amino)-substituted maleimide derivatives 4a - e , which are based on an acceptor-donor-acceptor (A-D-A) system, exhibited aggregation-induced emission enhancement (AIEE) properties in aqueous media. Compounds 4a and 4e , bearing electron-withdrawing groups (Br and CF 3 , respectively) showed 7.0 and 15 times fluorescence enhancement. Time-dependent density functional theory (TD-DFT) calculations were performed to gain better insight into the electronic nature of the compounds with and without AIEE properties.