Copper(I)-Mediated Cascade Annulation via Dual C–H/C–H Activation: Access to Benzo[a]carbazolic AEEgens

A Cu­(I)-mediated cascade cyclization/annulation of unprotected o-alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation of one C–N and two C–C bonds to deliver fused benzo­[a]­carbazoles having free NH skeletons. The annulated products display fluorescence emission in the range of 485–502 nm with a large Stokes shift and fluorescence lifetime of ∼17 ns. The annulated 3aa displays AEE behavior in the ethanol/hexane system and possesses marigold-flower-like morphology at the aggregated state. Cell viability assays enumerate biocompatible AEEgens, while their high intracellular fluorescence depicts cell imaging applicability.