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

Gila Levi, Yosef Scolnik, Yitzhak Mastai

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15 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 languageEnglish
Pages (from-to)23356-23361
Number of pages6
JournalACS applied materials & interfaces
Volume8
Issue number35
DOIs
StatePublished - 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.

FundersFunder number
Bar-Ilan Department of Chemistry
Weizmann Institute of Science
Ministry of Science, Technology and Space
Israel Science Foundation660/07

    Keywords

    • chiral surfactant
    • chirality
    • enantioselectivity
    • porous materials
    • silica nanomaterials

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