Abstract
<jats:p>While helicene derivatives have been widely recognized for their promise in advanced photonic technologies, their bioimaging applications are relatively unexplored. Herein, we report a three-step synthesis of aggregation-induced emission (AIE)-active azahelicenes, Aza[7]T, Aza[7]TM, and Aza[7]TOM, by combining a nitrogen-containing helical framework with triphenylamine derivatives. These molecules display red to deep-red emission and intense chiroptical responses, with dissymmetry factors reaching the 10-2 level. Among the series, Aza[7]TOM exhibited excellent lipid-droplet (LD) targeting specificity (Pearson’s colocalization coefficients R2 > 0.98), low cytotoxicity, high imaging brightness, and wash-free staining ability in living HeLa cells. Structure illumination microscopy super-resolution imaging further revealed well-defined intracellular LDs with sharp boundaries. Notably, Aza[7]TOM could also sense the maturation state of LDs, making it a valuable probe for studying LD dynamics and biogenesis.</jats:p>