Chiral Separation via Molecular Sieving: A Computational Screening of Suitable Functionalizations for Nanoporous Graphene

Samuel M. Fruehwirth, Ralf Meyer, Andreas W. Hauser

Research output: Contribution to journalArticleResearchpeer-review

Abstract

In a recent study [Angew. Chem. Int. Ed., 2014, 53, 9957–9960] a new concept of chiral separation has been suggested, which is based on functionalized, nanoporous sheets of graphene. In this follow-up article we discuss the underlying principle in greater detail and make suggestions for suitable pore functionalizations with respect to a selection of chiral prototype molecules. Considering drug molecules as future targets for a chiral separation via membranes, the necessary pore sizes represent a big challenge for standard methods of computational chemistry. Therefore, we test two common force fields (GAFF, CGenFF) as well as a semiempirical tight-binding approach recently developed by the Grimme group (GFN-xTB) against the computationally much more expensive density functional theory. We identify the GFN-xTB method as the most suitable approach for future simulations of functionalized pores for the given purpose, as it is able to produce reaction pathways in very good agreement with density functional theory, even in cases where force fields tend to an extreme overestimation of barrier heights.

Original languageEnglish
Pages (from-to)2331-2339
Number of pages9
JournalChemPhysChem
Volume19
Issue number18
DOIs
Publication statusPublished - 18 Sep 2018

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Graphite
Density functional theory
Screening
graphene
screening
Computational chemistry
porosity
field theory (physics)
Molecules
density functional theory
Pore size
computational chemistry
Membranes
suggestion
molecules
drugs
prototypes
Pharmaceutical Preparations
membranes
simulation

Keywords

  • chiral separation
  • force fields
  • molecular sieving
  • nanoporous materials
  • porous graphene
  • racemic mixtures
  • tight-binding method

ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics
  • Physical and Theoretical Chemistry

Fields of Expertise

  • Advanced Materials Science

Cite this

Chiral Separation via Molecular Sieving : A Computational Screening of Suitable Functionalizations for Nanoporous Graphene. / Fruehwirth, Samuel M.; Meyer, Ralf; Hauser, Andreas W.

In: ChemPhysChem, Vol. 19, No. 18, 18.09.2018, p. 2331-2339.

Research output: Contribution to journalArticleResearchpeer-review

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