Mesoporous carbon materials with enantioselective surface obtained by nanocasting for selective adsorption of chiral molecules from solution and the gas phase. (December 2020)

• Record Type: Journal Article
• Authors: Perovic, Milena; Aloni, Sapir Shekef; Mastai, Yitzhak; Oschatz, Martin
• Is Part Of: Carbon. Volume 170(2020)
• Page Start: 550
• Page End: 557
• Publication Date: 2020-12
• Subjects: Mesoporous carbon -- Chiral carbon -- Porous materials -- Enantiomers separation -- Chiral recognition -- Adsorption; Carbon -- Periodicals; Carbone -- Périodiques; Koolstof; Toepassingen; Electronic journals; 546.681
• DOI: 10.1016/j.carbon.2020.08.010
• Languages: English
• ISSNs: 0008-6223

Abstract

Abstract: Separation of enantiomers is an everlasting challenge in chemistry, catalysis, and synthesis of pharmaceuticals. The design and fabrication of chiral adsorbent materials is a promising way to increase the surface area of chiral information, as well as to maximize the available surface for the adsorption of one enantiomer. Porous materials such as silica or metal-organic-frameworks are established compounds in this field, due to their well-defined surface structure and ease of functionalization with chiral groups. As another class of porous materials, carbons provide the advantages of high thermal and chemical stability, resistance against moisture, electrical conductivity, and widely tunable pore size. Although they are well established in many adsorption-related applications, carbons received far less attention in enantioselective adsorption processes because the controlled functionalization of their surface is rather difficult due to the chemically heterogeneous atoms in the network. A suitable approach to overcome this limitation is the synthesis of chiral carbons directly from chiral precursors. So far, chiral carbons synthesized from chiral precursors used salt-templating as a way of introducing porosity, which resulted in mainly microporous materials or materials with broad pore size distribution. In the present study, the possibility of combining nanocasting as an alternative templating approach with chiral ionic liquids as a carbon precursor is demonstrated. Chiral recognition is measured in the gas phase, by adsorption of chiral gas, as well as in the solution, by using isothermal titration calorimetry. Graphical abstract: Graphical presentation of mesoporous chiral L-m-carbon (down left), and D-m-carbon (down right), together with their precursors – chiral ionic liquids, N, N, N-trimethyl-l -Tyrosine methyl ester tetrafluoroborate (top left), and N, N, N-trimethyl-d -Tyrosine methyl ester tetrafluoroborate (top right). Image 1