Synthesis and study of binaphthyl-based chiral dendrimers

1,1-Binaphthyl and bisbinaphthyl core-based optically active dendrimers containing phenylene or phenyleneethynylene dendrons have been synthesized and characterized. These materials have exhibited efficient light-harvesting properties with greatly increased fluorescence intensity as the dendritic generation increases. The fluorescent responses of these materials in the presence of chiral substrates such as amino alcohols and mandelic acid have been studied. Good enantioselective fluorescent recognitions have been observed. The light-harvesting effects of the dendrimers are found to greatly amplify their fluorescence responses towards both the fluorescent quenchers and enhancers. Thus, highly sensitive as well as enantioselective fluorescent sensors have been obtained. These sensors will be useful in the high throughput combinatorial chiral catalyst screening.