title: Enantioselective fluorescent recognition in the fluorous phase: enhanced reactivity and expanded chiral recognition.
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.
authors.affiliation: †Department of Chemistry, University of Virginia, Charlottesville, Virginia 2290, United States.
authors.forename: Chao
authors.initials: C
authors.lastname: Wang
authors.affiliation: †Department of Chemistry, University of Virginia, Charlottesville, Virginia 2290, United States.
authors.forename: Elaine
authors.initials: E
authors.lastname: Wu
authors.affiliation: †Department of Chemistry, University of Virginia, Charlottesville, Virginia 2290, United States.
authors.forename: Xuedan
authors.initials: X
authors.lastname: Wu
authors.affiliation: ‡CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
authors.forename: Xiangchuan
authors.initials: X
authors.lastname: Xu
authors.affiliation: ‡CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
authors.forename: Guoqing
authors.initials: G
authors.lastname: Zhang
authors.affiliation: †Department of Chemistry, University of Virginia, Charlottesville, Virginia 2290, United States.
authors.forename: Lin
authors.initials: L
authors.lastname: Pu