Multi-stimuli-responsive fluorescence of axially chiral 4-ene-β-Diketones

Dehua Wu ^a,1, Xinyi Fang ^b,c,1, Jintong Song ^a, Lang Qu ^a, Xiangge Zhou ^a, Haifeng Xiang ^a,*, Jun Wang ^b,**, Jin Liu ^c,***

Dyes and Pigments 184 (2021) 108851

A unique series of simple, smart, and chiral binaphthalene-substituted 4-ene-β-diketones molecules has been designed and prepared. Their optical properties, charge contribution, and transition process highly depend on their chemical structures. These π-conjugated materials are highly emissive in both solution and solid (emission quantum yield up to 68%), owing to the inhibition of enol-keto tautomerization and the effect of steric hindrance from binaphthalene. Through ethylenic bond hydrolysis, they can be used for not only cation/anion sensing but also chiral amino acids recognition. Moreover, at low concentrations, they have little cytotoxicity to living cells and can stain cytoplasm. Therefore, they afford a new platform in the design of multi-stimuli-responsive, smart, and chiral materials.