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

Ming Hu, Feng‐Ying Ye, Cong Du, Weizhou Wang, Wei Yu, Minghua Liu, Yan‐Song Zheng

2021Angewandte Chemie International Edition64 citationsDOI

Abstract

Abstract 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.

Topics & Concepts

TetraphenylethyleneFluorescenceLuminescenceEnantiomerEnantioselective synthesisMaterials scienceChemistryTartaric acidCombinatorial chemistryPhotochemistryStereochemistryAggregation-induced emissionOptoelectronicsOrganic chemistryPhysicsCatalysisCitric acidQuantum mechanicsLuminescence and Fluorescent MaterialsSynthesis and Properties of Aromatic CompoundsMolecular Sensors and Ion Detection
Hindered Tetraphenylethylene Helicates: Chiral Fluorophores with Deep‐Blue Emission, Multiple‐Color CPL, and Chiral Recognition Ability | Litcius