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Viewing and Inducing Symmetry Breaking at the Single‐Molecule Limit
Author(s) -
Tierney Heather L.,
Jewell April D.,
Baber Ashleigh E.,
Iski Erin V.,
Sykes E. Charles H.
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22096
Subject(s) - chirality (physics) , chemistry , enantiomer , symmetry breaking , enantioselective synthesis , chiral symmetry breaking , chemical physics , scanning tunneling microscope , molecule , nanotechnology , stereochemistry , physics , nambu–jona lasinio model , quantum mechanics , organic chemistry , catalysis , materials science
Symmetry breaking by photons, electrons, and molecular interactions lies at the heart of many important problems as varied as the origin of homochiral life to enantioselective drug production. Herein we report a system in which symmetry breaking can be induced and measured in situ at the single‐molecule level using scanning tunneling microscopy. We demonstrate that electrical excitation of a prochiral molecule on an achiral surface produces large enantiomeric excesses in the chiral adsorbed state of up to 39%. The degree of symmetry breaking was monitored as a function of scanning probe tip state, and the results revealed that enantiomeric excesses are correlated with the intrinsic chirality in scanning probe tips themselves, as evidenced by height differences between single molecule enantiomers. While this work has consequences for the study of two‐dimensional chirality, more importantly, it offers a new method for interrogating the coupling of photons, electrons, and combinations of physical fields to achiral starting systems in a reproducible manner. This will allow the mechanism of chirality transfer to be studied in a system in which enantiomeric excesses are quantified accurately by counting individual molecules. Chirality 24:1051–1054, 2012 . © 2012 Wiley Periodicals, Inc.