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Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation

[Image: see text] Chiral separation and asymmetric synthesis and catalysis are crucial processes for obtaining enantiopure compounds, which are especially important in the pharmaceutical industry. The efficiency of the separation processes is readily increased by using porous materials as the active...

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Autores principales: Perovic, Milena, Aloni, Sapir Shekef, Zhang, Wuyong, Mastai, Yitzhak, Antonietti, Markus, Oschatz, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8289191/
https://www.ncbi.nlm.nih.gov/pubmed/33977720
http://dx.doi.org/10.1021/acsami.1c02673
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author Perovic, Milena
Aloni, Sapir Shekef
Zhang, Wuyong
Mastai, Yitzhak
Antonietti, Markus
Oschatz, Martin
author_facet Perovic, Milena
Aloni, Sapir Shekef
Zhang, Wuyong
Mastai, Yitzhak
Antonietti, Markus
Oschatz, Martin
author_sort Perovic, Milena
collection PubMed
description [Image: see text] Chiral separation and asymmetric synthesis and catalysis are crucial processes for obtaining enantiopure compounds, which are especially important in the pharmaceutical industry. The efficiency of the separation processes is readily increased by using porous materials as the active material can interact with a larger surface area. Silica, metal–organic frameworks, or chiral polymers are versatile porous materials that are established in chiral applications, but their instability under certain conditions in some cases requires the use of more stable porous materials such as carbons. In addition to their stability, porous carbon materials can be tailored for their ability to adsorb and catalytically activate different chemical compounds from the liquid and the gas phase. The difficulties imposed by the functionalization of carbons with chiral species were tackled in the past by carbonizing chiral ionic liquids (CILs) together with a template to create pores, which results in the entire body of a material that is built up from the precursor. To increase the atomic efficiency of ionic liquids for better economic utilization of CILs, the approach presented here is based on the formation of a composite between CIL-derived chiral carbon and a pristine carbon material obtained from carbohydrate precursors. Two novel enantioselective carbon composite materials are applied for the chiral recognition of molecules in the gas phase, as well as in solution. The enantiomeric ratio of the l-composite for phenylalanine from the solution was (L/D) = 8.4, and for 2-butanol from the gas phase, it was (S/R) = 1.3. The d-composite showed an opposite behavior, where the enantiomeric ratio for phenylalanine was (D/L) = 2.7, and for 2-butanol from the gas phase, it was (R/S) = 1.3.
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spelling pubmed-82891912021-07-20 Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation Perovic, Milena Aloni, Sapir Shekef Zhang, Wuyong Mastai, Yitzhak Antonietti, Markus Oschatz, Martin ACS Appl Mater Interfaces [Image: see text] Chiral separation and asymmetric synthesis and catalysis are crucial processes for obtaining enantiopure compounds, which are especially important in the pharmaceutical industry. The efficiency of the separation processes is readily increased by using porous materials as the active material can interact with a larger surface area. Silica, metal–organic frameworks, or chiral polymers are versatile porous materials that are established in chiral applications, but their instability under certain conditions in some cases requires the use of more stable porous materials such as carbons. In addition to their stability, porous carbon materials can be tailored for their ability to adsorb and catalytically activate different chemical compounds from the liquid and the gas phase. The difficulties imposed by the functionalization of carbons with chiral species were tackled in the past by carbonizing chiral ionic liquids (CILs) together with a template to create pores, which results in the entire body of a material that is built up from the precursor. To increase the atomic efficiency of ionic liquids for better economic utilization of CILs, the approach presented here is based on the formation of a composite between CIL-derived chiral carbon and a pristine carbon material obtained from carbohydrate precursors. Two novel enantioselective carbon composite materials are applied for the chiral recognition of molecules in the gas phase, as well as in solution. The enantiomeric ratio of the l-composite for phenylalanine from the solution was (L/D) = 8.4, and for 2-butanol from the gas phase, it was (S/R) = 1.3. The d-composite showed an opposite behavior, where the enantiomeric ratio for phenylalanine was (D/L) = 2.7, and for 2-butanol from the gas phase, it was (R/S) = 1.3. American Chemical Society 2021-05-12 2021-05-26 /pmc/articles/PMC8289191/ /pubmed/33977720 http://dx.doi.org/10.1021/acsami.1c02673 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Perovic, Milena
Aloni, Sapir Shekef
Zhang, Wuyong
Mastai, Yitzhak
Antonietti, Markus
Oschatz, Martin
Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation
title Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation
title_full Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation
title_fullStr Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation
title_full_unstemmed Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation
title_short Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation
title_sort toward efficient synthesis of porous all-carbon-based nanocomposites for enantiospecific separation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8289191/
https://www.ncbi.nlm.nih.gov/pubmed/33977720
http://dx.doi.org/10.1021/acsami.1c02673
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