Optically active BINOL core-based phenyleneethynylene dendrimers for the enantioselective fluorescent recognition of amino alcohols

被引:104
作者
Pugh, VJ
Hu, QS
Zuo, XB
Lewis, FD
Pu, L [1 ]
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA
[2] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
D O I
10.1021/jo010479t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A dramatic enhancement in fluorescence intensity from 1,1 ' -bi-2-naphthol (BINOL) to dendritic phenyleneethynylenes containing the BINOL core was observed. The strong fluorescence of the dendrimers allows a very small amount of the chiral materials to be used for sensing. The light harvesting antennas of the dendrimer funnel energy to the center BINOL unit, whose hydroxyl groups upon interaction with a quencher molecule lead to fluorescence quenching. This mechanism makes the dendrimers have much more sensitive fluorescence responses than corresponding small molecule sensors. The fluorescence of these dendrimers can be enantioselectively quenched by chiral amino alcohols. It is observed that the fluorescence lifetime of the generation two dendrimer does not change in the presence of various concentrations of 2-amino-3-phenyl-1-propanol. This demonstrates that the fluorescence quenching is entirely due to static quenching. Thus, formation of nonfluorescent ground-state hydrogen-bond complexes between the dendrimers and amino alcohols is proposed to account for the fluorescent quenching. A linear relationship has been established between the Stern-Volmer constant of the generation two dendrimer and the enantiomeric composition of 2-amino-3-phenyl-1-propanol. Such enantioselective fluorescent sensors may allow a rapid determination of the enantiomeric composition of chiral molecules and are potentially useful in the combinatorial search of asymmetric catalysts and reagents.
引用
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页码:6136 / 6140
页数:5
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