Host-guest assembly for highly sensitive probing of a chiral monoalcohol with a zinc trisporphyrinate
Cong-Cong Zhuo1, Li Li1, Chuan-Jiang Hu1,2 *（胡传江）& Jian-Ping Lang1*（郎建平）
1State 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.
2Applied Technology College of Soochow University, Suzhou, 215325, Jiangsu, P.R. China.
Scientific Reports ，2017，7: 3829
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 K1 is over 105 M−1, 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.
链接：http://www.nature.com/articles/s41598-017-03441-1
