Hindered Tetraphenylethylene Helicates: Chiral Fluorophores with Deep-Blue Emission, Multiple-Color CPL, and Chiral Recognition Ability.
Ming HuFeng-Ying YeCong DuWeizhou WangWei YuMinghua LiuYan-Song ZhengPublished in: Angewandte Chemie (International ed. in English) (2021)
New hindered tetraphenylethylene (TPE) helicates with substitution at 2,6-position of phenyl rings were designed and synthesized. Due to the increased hindrance, the TPE helicates emit strong deep-blue to violet fluorescence both in the solid state and in solution, and could be resolved into enantiomers that emit strong and multicolor circularly polarized luminescence (CPL), and exhibit a high enantioselective recognition of chiral tartaric acid and its derivatives. Surprisingly, the derived helicate tetramines possess amino groups with an unpredented planar structure and sp 2 -hybridized nitrogen, arousing the change between AIE effect and ACQ phenomenon through photoinduced electron transfer (PET). With advantages of short synthetic route, many modification positions, deep-blue to violet emission, wide CPL tuning, and high chiral recognition ability, the hindered TPE helicates show broad prospects as chiral materials.