Cited by 79Surface Chemistry and CatalysisElectron and X-Ray Spectroscopy TechniquesMolecular Junctions and Nanostructures

Chiral Selective Chemistry Induced by Natural Selection of Spin‐Polarized Electrons

Rosenberg, Richard A., Mishra, Debabrata, Naaman, Ron·2015·Angewandte Chemie International Edition

Abstract

The search to understand the origin of homochirality in nature has been ongoing since the time of Pasteur. Previous work has shown that DNA can act as a spin filter for low‐energy electrons and that spin‐polarized secondary electrons produced by X‐ray irradiation of a magnetic substrate can induce chiral selective chemistry. In the present work it is demonstrated that secondary electrons from a substrate that are transmitted through a chiral overlayer cause enantiomeric selective chemistry in an adsorbed adlayer. We determine the quantum yields (QYs) for dissociation of (R)‐ or (S)‐epichlorohydrin adsorbed on a chiral self‐assembled layer of DNA on gold and on bare gold (for control). The results show that there is a significant difference in the QYs between the two enantiomers when adsorbed on DNA, but none when they are adsorbed on bare Au. We propose that the effect results from natural spin filtering effects cause by the chiral monolayer.

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Crossref · 10.1002/anie.201501678

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Authors
Rosenberg, R. A., Mishra, D., & Naaman, R.
Affiliations
  • Argonne National Laboratory (US)
  • Weizmann Institute of Science (IL)
Corresponding author
Rosenberg, Richard A.
Venue
Angewandte Chemie International Edition
Publisher
Wiley
Published
2015-05-07
Volume
54
Issue
25
Pages
7295-7298
ISSN
  • 1433-7851 (ISSN-L)
  • 1521-3773
OpenAlex
W2116570557
Cited by
79
References
27
Citations by year
2026: 1 · 2025: 13 · 2024: 5 · 2023: 7 · 2022: 9 · 2021: 11 · 2020: 6 · 2019: 11 · 2018: 3 · 2017: 8 · 2016: 5
FWCI
2.65
Type
journal article
Language
en
Open access
closed
Locations
  • Angewandte Chemie International Edition (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Engineering › Biomedical Engineering › Surface Chemistry and Catalysis
  • Physical Sciences › Materials Science › Surfaces, Coatings and Films › Electron and X-Ray Spectroscopy Techniques
  • Physical Sciences › Engineering › Electrical and Electronic Engineering › Molecular Junctions and Nanostructures
Keywords
origin of homochirality, chiral selectivity, polarized electrons, spin filtering, DNA, epichlorohydrin, enantioselectivity, quantum yield, gold substrate
MeSH terms
Adsorption, Chlorohydrins, Electrons, Gold, Models, Molecular, Stereoisomerism, Surface Properties, X-Rays, Photoelectron Spectroscopy, Immobilized Nucleic Acids

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