An Expanded EDA Complex Profile: Construction of Aza-arenes and Their Synthetic Application as Fluorescence Probes.

ABSTRACT

We developed a visible-light-driven expanded EDA complex profile for the synthesis of aza-arenes via aza-6π electrocyclization of 2-styrylanilines with aromatic aldehydes. This protocol relies on the EDA complexes of AlCl3 with imine to induce the absorption red-shift to visible light from ultraviolet light. An array of 2,3-disubstituted quinolines were constructed smoothly after excitation with blue-light-emitting diodes at room temperature. In addition, the resultant product, used as a cell permeable lipid droplet-specific probe, shows a low working concentration, a short staining time, and functionality in living and fixed cells.