Wang Qin, Chen Xi, Tao Lan, Wang Li, Xiao Dan, Yu Xiao-Qi, Pu Lin
Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), Sichuan University, Chengdu, Sichuan 610064, China.
J Org Chem. 2007 Jan 5;72(1):97-101. doi: 10.1021/jo061769i.
The tetrahydroxyl derivative of BINOL, (S)- or (R)-1, and its analogues are synthesized. (S)- or (R)-1 can be used to conduct the enantioselective recognition of chiral amino alcohols. In comparison with BINOL, the two additional hydroxyl groups of (S)- or (R)-1 have increased the binding of this compound with the amino alcohols and significantly improved the fluorescence quenching efficiency. The fluorescence responses of (S)- or (R)-1 toward amino alcohols are compared with those of its analogues (R)-4 and (R)-6. It shows that the interaction of the central naphthyl hydroxyl groups of (S)- or (R)-1 with the substrates is responsible for the observed fluorescence quenching, and the two additional alkyl hydroxyl groups increase the quenching efficiency.
合成了联萘酚的四羟基衍生物（S）-或（R）-1及其类似物。（S）-或（R）-1可用于对手性氨基醇进行对映选择性识别。与联萘酚相比，（S）-或（R）-1的两个额外羟基增加了该化合物与氨基醇的结合，并显著提高了荧光猝灭效率。将（S）-或（R）-1对氨基醇的荧光响应与其类似物（R）-4和（R）-6的荧光响应进行了比较。结果表明，（S）-或（R）-1的中心萘基羟基与底物的相互作用导致了观察到的荧光猝灭，而两个额外的烷基羟基提高了猝灭效率。
