Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid

Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines from alpha-bromocinnamaldehyde and 2-substituted benzimidazoles. The reaction promoted by a simple inorganic base displays moderate to good yields and good functional group tolerance. The optical properties of some typical products have been investigated. We found that, due to the presence of the benzene ring at the C1-position of benzo[4,5]imidazo[1,2-a]pyridines which restricts intramolecular motion, as a new type of aggregation-induced emission (AIE) luminogen (AIEgen), they show very good solid-state fluorescence with quantum yields up to 88.80%. Importantly, the AIE performance of compound 3b can be useful to detect the nitroaromatic explosive picric acid (PA) with a detection limit and quenching constant of 42.5 nM and 7.27 x 10(4) M-M, respectively.

Automated summary

Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines, showing good yields and functional group tolerance. The newly synthesized compounds exhibit excellent solid-state fluorescence as aggregation-induced emission luminogens (AIEgens), with some products capable of detecting nitroaromatic explosives like picric acid.