Imprinting chirality in silica nanotubes by N-stearoyl-serine template

Gila Levi; Yosef Scolnik; Yitzhak Mastai

doi:10.1021/acsami.6b06540

Imprinting chirality in silica nanotubes by N-stearoyl-serine template

Gila Levi, Yosef Scolnik, Yitzhak Mastai

Department of Chemistry

Iyar

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

In this article, we describe the synthesis of imprinted chiral silica nanotubes based on the use of a chiral N-stearoyl l-serine (C₁₈Ser) anionic surfactant as the chiral template. The resulting chiral silica nanotube structures were characterized by electronic microscopy (transmission electron microscopy (TEM) and scanning electron microscopy (SEM)) and nitrogen isotherms that proved the formation of well-ordered silica nanotubes. A C₁₈Ser surfactant template was used for the preparation of the silica nanotubes, due to its effective molecular organization within the silica network. After chemical extraction of the chiral template, the enantioselectivity feature of the silica nanotubes was confirmed by selective adsorption of the enantiomers using circular dichroism (CD) and isothermal titration calorimetry (ITC) measurements. Although these measurements show a relatively low chiral selectivity of the silica nanotubes (ca. 6% enantiomeric excess), the system described here offers new approaches for the application of chiral porous materials in chirality.

Original language	English
Pages (from-to)	23356-23361
Number of pages	6
Journal	ACS applied materials & interfaces
Volume	8
Issue number	35
DOIs	https://doi.org/10.1021/acsami.6b06540
State	Published - 7 Sep 2016

Bibliographical note

Publisher Copyright:
© 2016 American Chemical Society.

Funding

G.L. would like to acknowledge Dr. Yochai Basel for his help and support during the research project. G.L. acknowledges the Bar-Ilan Department of Chemistry for funding. This research was supported by the Israel Science Foundation (grant No. 660/07) and by the Ministry of Science, Technology and Space. The authors dedicate this article in memory of our colleague, Prof. Meir Shinitzky, Weizmann Institute of Science, who passed away in December 2015.

Funders	Funder number
Bar-Ilan Department of Chemistry
Weizmann Institute of Science
Ministry of Science, Technology and Space
Israel Science Foundation	660/07

Keywords

chiral surfactant
chirality
enantioselectivity
porous materials
silica nanomaterials

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abstract = "In this article, we describe the synthesis of imprinted chiral silica nanotubes based on the use of a chiral N-stearoyl l-serine (C18Ser) anionic surfactant as the chiral template. The resulting chiral silica nanotube structures were characterized by electronic microscopy (transmission electron microscopy (TEM) and scanning electron microscopy (SEM)) and nitrogen isotherms that proved the formation of well-ordered silica nanotubes. A C18Ser surfactant template was used for the preparation of the silica nanotubes, due to its effective molecular organization within the silica network. After chemical extraction of the chiral template, the enantioselectivity feature of the silica nanotubes was confirmed by selective adsorption of the enantiomers using circular dichroism (CD) and isothermal titration calorimetry (ITC) measurements. Although these measurements show a relatively low chiral selectivity of the silica nanotubes (ca. 6% enantiomeric excess), the system described here offers new approaches for the application of chiral porous materials in chirality.",

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Imprinting chirality in silica nanotubes by N-stearoyl-serine template

Abstract

Bibliographical note

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Keywords

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