State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, Jiangsu, P.R. China.
Applied Technology College of Soochow University, Suzhou, 215325, Jiangsu, P.R. China.
Sci Rep. 2017 Jun 19;7(1):3829. doi: 10.1038/s41598-017-03441-1.
A zinc trisporphyrinate has been developed as a chirality sensor for chiral mono-alcohols. In its structure, there are two "spaces" surrounded by three porphyrin moieties, which allow guests to fill in. It has shown extremely high CD sensitivity for a chiral mono-alcohol with a naphthyl substituent, 1-(1-naphthyl)ethanol, at μM level, which is at least three orders of magnitude lower concentration than previous reports. A crystallographic study of the host-guest complex reveals the binding of 1-(1-naphthyl)ethanol to the zinc trisporphyrinate is greatly enhanced by multipoint interactions, such as coordination interactions, hydrogen bonding, π-π and CH···π interactions etc. Spectroscopic studies suggest the corresponding binding constant K is over 10 M, which is two or three orders of magnitude larger than other mono-alcohols. Among porphyrin systems, this trisporphyrin have the strongest binding affinity for 1-(1-naphthyl)ethanol, which leads to the highest CD sensitivity.
一种锌三吡咯啉已被开发为手性单醇的手性传感器。在其结构中，有两个“空间”被三个卟啉部分包围，允许客体填充。它对具有萘基取代基的手性单醇，1-（1-萘基）乙醇，在μM 水平表现出极高的 CD 灵敏度，比以前的报道至少低三个数量级。对主体-客体配合物的晶体学研究表明，1-（1-萘基）乙醇与锌三吡咯啉的结合通过多点相互作用（如配位相互作用、氢键、π-π 和 CH···π 相互作用等）得到极大增强。光谱研究表明，相应的结合常数 K 超过 10 M，比其他单醇大两个或三个数量级。在卟啉体系中，这种三吡咯啉对 1-（1-萘基）乙醇具有最强的结合亲和力，从而导致最高的 CD 灵敏度。
