Xu Ming-Hua, Lin Jing, Hu Qiao-Sheng, Pu Lin
Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319, USA.
J Am Chem Soc. 2002 Nov 27;124(47):14239-46. doi: 10.1021/ja020989k.
Novel chiral bisbinaphthyl compounds have been synthesized for the enantioselective fluorescent recognition of mandelic acid. By introducing dendritic branches to the chiral receptor unit, the fluorescence signals of the receptors are significantly amplified because of the light-harvesting effect of the dendritic structure. This has greatly increased the sensitivity of the sensors in the fluorescent recognition. Study of the three generation sensors demonstrates that the generation zero sensor is the best choice for the recognition of mandelic acid because of its greatly increased fluorescence signal over the core and its high enantioselectivity. This sensor is potentially useful for the high throughput screening of chiral catalysts for the asymmetric synthesis of alpha-hydroxycarboxylic acids.
