Hindered Tetraphenylethylene Helicates: Chiral Fluorophores with Deep-Blue Emission, Multiple-Color CPL, and Chiral Recognition Ability.

Angew Chem Int Ed Engl

Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, 430074, China.

Published: February 2022

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 -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.

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http://dx.doi.org/10.1002/anie.202115216DOI Listing

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