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Induction of Homochirality in Achiral Enantiomorphous Monolayers
Abstract
We report the induction of homochirality in enantiomorphous layers of achiral succinic acid on a Cu(110) surface after doping with tartaric acid (TA) enantiomers. Succinic acid becomes chiral upon adsorption due to symmetry-breaking interactions with the Cu(110) surface. The doubly deprotonated bisuccinate forms mirror domains on the surface, which leads to a superposition of (11,-90) and (90,-11) patterns observed by low-energy electron diffraction (LEED). On average, however, the surface layer is racemic. An amount of 2 mol % of (R,R)- or (S,S)-tartaric acid in the monolayer, corresponding to an absolute coverage of 0.001 tartaric acid molecule per surface copper atom, is sufficient to make the LEED spots of one enantiomorphous lattice disappear. After thermally induced desorption of TA, the succinic acid lattice turns racemic again. In analogy to the "sergeants-and-soldiers" principle described for helical polymers, this effect is explained by a lateral cooperative interaction within the two-dimensional lattice.
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Citations
Cited by
Park, J.-W., & Shumaker-Parry, J. S. (2014) · Journal of the American Chemical Society · doi:10.1021/ja4097384 · Cited by 708
Crystalline Architectures as Templates of Relevance to the Origins of Homochirality
Weissbuch, I., & Lahav, M. (2011) · Chemical Reviews · doi:10.1021/cr1002479 · Cited by 284
Molecular chirality at surfaces
Ernst, K. (2012) · physica status solidi (b) · doi:10.1002/pssb.201248188 · Cited by 260
Self-citationChirality in adsorption on solid surfaces
Zaera, F. (2017) · Chemical Society Reviews · doi:10.1039/c7cs00367f · Cited by 172
Adsorption-induced auto-amplification of enantiomeric excess on an achiral surface
Yun, Y., & Gellman, A. J. (2015) · Nature Chemistry · doi:10.1038/nchem.2250 · Cited by 81
Metadata
- Authors
- Parschau, M., Romer, S., & Ernst, K.-H.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-11-04
- Volume
- 126
- Issue
- 47
- Pages
- 15398-15399
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2039556503
- Cited by
- 167
- References
- 0
- FWCI
- 4.04
- Type
- journal article
- Language
- en
- Open access
- closed
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- Parschau, M., Romer, S., & Ernst, K.-H. (2004). Induction of Homochirality in Achiral Enantiomorphous Monolayers. Journal of the American Chemical Society. https://doi.org/10.1021/ja044136z
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