Host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate

Abstract 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 sub...

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Autores principales:	Cong-Cong Zhuo, Li Li, Chuan-Jiang Hu, Jian-Ping Lang
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/e30a7d005c884d7092e9910c6ffcb2d6
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spelling	oai:doaj.org-article:e30a7d005c884d7092e9910c6ffcb2d62021-12-02T12:32:07ZHost-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate10.1038/s41598-017-03441-12045-2322https://doaj.org/article/e30a7d005c884d7092e9910c6ffcb2d62017-06-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-03441-1https://doaj.org/toc/2045-2322Abstract 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.Cong-Cong ZhuoLi LiChuan-Jiang HuJian-Ping LangNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-7 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Cong-Cong Zhuo Li Li Chuan-Jiang Hu Jian-Ping Lang Host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate
description	Abstract 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.
format	article
author	Cong-Cong Zhuo Li Li Chuan-Jiang Hu Jian-Ping Lang
author_facet	Cong-Cong Zhuo Li Li Chuan-Jiang Hu Jian-Ping Lang
author_sort	Cong-Cong Zhuo
title	Host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate
title_short	Host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate
title_full	Host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate
title_fullStr	Host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate
title_full_unstemmed	Host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate
title_sort	host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/e30a7d005c884d7092e9910c6ffcb2d6
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_version_	1718394188738854912

Host-guest assembly for highly sensitive probing of a chiral mono-alcohol with a zinc trisporphyrinate

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