Chiral Macrocyclic AIEgens from BINOL and Tetraphenylethene via Tailoring Chirality of Luminescent Molecular Propellers

Abstract

Comprehensive SummaryHerein, a pair of chiral macrocyclic luminogens derived from chiral 1,1‐bi(2‐naphthol) (BINOL) and tetraphenylethenes (TPEs) have been prepared with high yield via intramolecular McMurry coupling, in which the preferential helicity of propeller‐shaped TPE units can be tuned via choosing proper chiral BINOL tethers. The preferential chiral geometry of the macrocyclic luminogen was unambiguously confirmed by X‐ray crystal crystallography and theoretical calculation, whereas the variable‐temperature NMR spectra and chiral HPLC analysis further verified the intramolecular motions. These two chiral macrocyclic luminogens both exhibit obvious aggregation‐induced emission behavior and mechanochromic luminescence properties. Furthermore, aggregation attenuated CD signals and circularly polarized luminescence were observed for these two chiral macrocylic luminogens in THF‐water mixture and PMMA matrix. These results had paved a new approach toward constructing chiral aggregation‐induced emission luminogens (AIEgens) and their structural engineering.