Tetraphenylethylene dicycle helicates: circularly polarized luminescence and chiral recognition based on emission wavelength change  

作　　者：Zhi-Rong Xu Miao-Li Gao Ming Hu Wei Yu Yan-Song Zheng 

机构地区：[1]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

出　　处：《Science China Chemistry》2024年第11期3817-3824,共8页中国科学（化学英文版）

基　　金：the National Natural Science Foundation of China (22072050 and 22372066) for financial support。

摘　　要：Chiral tetraphenylethylene(TPE) dicycle tetraaldehyde and TPE dicycle tetraacids bearing optically pure groups on the cycles were designed and synthesized. Due to the propeller-like conformation immobilization of TPE unit, this new class of TPE dicycle was resolved into M-and P-enantiomers, which could emit strong circular polarized luminescence(CPL). Interestingly,these TPE helicates displayed exceptional ability of molecule recognition. While the TPE dicycle tetraaldehyde could detect the microscale water in anhydrous tetrahydrofuran, the chiral TPE dicycle tetraacid could display different fluorescent color after interacting with two enantiomers of a wide variety of chiral amines including monoamines, diamines, and aminols, which could be applied to chiral recognition of these chiral amines. Furthermore, the emission wavelength of TPE dicycle tetraacid was found to change linearly with the enantiomer purity of chiral amine from enantiomer excess(ee) percent-100% to +100%, for the first time showing the potential for quantitative chiral analysis of chiral amines based on emission wavelength change. The emission wavelength was affected less by environmental factors than fluorescence intensity, which would enable the chiral analysis based on wavelength change with higher accuracy and repeatability.

关 键 词：TPE dicycle helicate CPL chiral recognition enantiomer excess analysis emission wavelength change 

分 类 号：O436.3[机械工程—光学工程] TQ207[理学—光学]