Enantioselective fluorescent recognition in the fluorous phase: enhanced reactivity and expanded chiral recognition

Journal of the American Chemical Society
Chao WangLin Pu

Abstract

A novel perfluoroalkyl-BINOL-based chiral diketone is found to be the first highly enantioselective fluorescent sensor in the fluorous phase. One enantiomer of a chiral amino alcohol or diamine at a concentration greater than 1 mM can cause an up to 1200-2000-fold fluorescent enhancement of the sensor (0.08 mM), while the other enantiomer gives only a 10-50-fold enhancement. The fluorous-phase-based sensor is found to enhance the reactivity of the previously reported fluorous insoluble sensor with amino alcohols and expand its chiral recognition ability. Dynamic light scattering studies show the formation of aggregates of very different particle sizes when two enantiomers of a substrate interact with the sensor in perfluorohexane (FC-12). This substantial difference enables easy discrimination of the enantiomers with UV-lamps or even the naked eye. NMR, IR, and mass spectroscopic studies indicate that the fluorescent enhancement and enantioselectivity should originate from the fluorous solvent-promoted nucleophilic addition of the amino alcohols to the carbonyl groups of the sensor.

References

Mar 7, 2002·Journal of the American Chemical Society·Jing LinLin Pu
Mar 11, 2004·Chemical Reviews·Lin Pu
Jun 29, 2004·Angewandte Chemie·Jianzhang ZhaoTony D James
Nov 13, 2004·Journal of the American Chemical Society·Xuefeng Mei, Christian Wolf
Apr 26, 2011·Topics in Current Chemistry·Alessandro AccettaRosangela Marchelli
Jul 30, 2011·Chemical Society Reviews·Yuning HongBen Zhong Tang
Aug 13, 2011·Accounts of Chemical Research·Lin Pu
Sep 6, 2011·Chemical Society Reviews·Diana LeungEric V Anslyn
Feb 7, 2014·Chemical Reviews·Xin ZhangJuyoung Yoon

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Citations

Jul 5, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Yuying JiangJianzhuang Jiang
May 29, 2018·Chemistry : a European Journal·Xiaojing LiYixiang Cheng
Sep 25, 2018·Chemical Communications : Chem Comm·Diksha GambhirRik Rani Koner
Sep 15, 2018·Chemical Communications : Chem Comm·Aditya N Khanvilkar, Ashutosh V Bedekar
Mar 21, 2019·Chemistry : a European Journal·Yuan-Yuan ZhuLin Pu
Jun 28, 2019·Organic & Biomolecular Chemistry·Samantha L PilicerChristian Wolf
Nov 2, 2019·Journal of Separation Science·Datong WuYong Kong
Jun 4, 2016·Chemistry, an Asian Journal·Li ZhangMinghua Liu
Sep 4, 2020·Angewandte Chemie·Johnny HuHenri-Pierre Jacquot de Rouville
Jul 31, 2018·Journal of the American Chemical Society·Brenden T HerreraChristian Wolf
Oct 3, 2018·ACS Applied Materials & Interfaces·Xiaobo ShangJoon Hak Oh

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