4.8 Article

Asymmetric Elimination Reaction on Chiral Metal Surfaces

期刊

ADVANCED MATERIALS
卷 34, 期 2, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adma.202104481

关键词

asymmetric catalysis; chiral materials; intermetallic compounds; surface chemistry; surface enantiomers

资金

  1. Swiss National Science Foundation [159690, 175923, 51NF40182892]
  2. ETH-Bereich Forschungsanstalten

向作者/读者索取更多资源

This study investigates the dehalogenation of prochiral 5-bromo-7-methylbenz(a)anthracene (BMA) on prototypical, chiral, intermetallic PdGa{111} surfaces under ultrahigh vacuum conditions, demonstrating asymmetric halogen elimination and a significant dependence on the atomic termination of the PdGa{111} surfaces for the dehalogenation temperature of the BMA surface enantiomers.
The production of enantiopure materials and molecules is of uttermost relevance in research and industry in numerous contexts, ranging from nonlinear optics to asymmetric synthesis. In the context of the latter, dehalogenation, which is an essential reaction step for a broad class of chemical reactions, is investigated; specifically, dehalogenation of prochiral 5-bromo-7-methylbenz(a)anthracene (BMA) on prototypical, chiral, intermetallic PdGa{111} surfaces under ultrahigh vacuum conditions. Asymmetric halogen elimination is demonstrated by combining temperature-programmed X-ray photoelectron spectroscopy, scanning probe microscopy, and density functional theory. On the PdGa{111} surfaces, the difference in debromination temperatures for the two BMA surface enantiomers amounts up to an unprecedented 46 K. The significant dependence of the dehalogenation temperature of the BMA surface enantiomers on the atomic termination of the PdGa{111} surfaces implies that the ensemble effect is pronounced in this reaction step. These findings evidence enantiospecific control and hence promote intrinsically chiral crystals for asymmetric on-surface synthesis.

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