Multifunctional 3-cyanopyridine compounds: synthesis based on a tandem reaction with 100% atom economy and their applications

Abstract

Employing a tandem reaction with 100% atom economy, a series of novel 3-cyanopyridine derivatives were synthesized from benzopyranonitriles and pyrrolidines under mild and metal-free conditions, promoted by sodium hydroxide, achieving yields up to 97%. The mechanism of this novel tandem reaction was confirmed by DFT calculations. These products exhibit aggregation-induced emission (AIE) and dual-state emission (DSE) effects due to restricted intramolecular motion (RIM) and a distorted structure resulting from the existence of a dihedral angle in the molecular structure. Notably, different 3-cyanopyridine compounds can be applicable for the “turn-off” detection of Fe³⁺/Cu²⁺ and various nitroaromatic compounds (NACs). Furthermore, these molecules have good antibacterial activity against Escherichia coli and Staphylococcus aureus, providing a novel strategy for the synthesis of new antimicrobial agents.