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Chiral Selective Chemistry Induced by Natural Selection of Spin‐Polarized Electrons
Author(s) -
Rosenberg Richard A.,
Mishra Debabrata,
Naaman Ron
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501678
Subject(s) - homochirality , chemistry , overlayer , electron , photochemistry , chemical physics , enantioselective synthesis , monolayer , adsorption , enantiomer , organic chemistry , physics , biochemistry , quantum mechanics , catalysis
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.