ArticleLangmuir : the ACS journal of surfaces and colloids2021
Influence of N-Substituents on the Adsorption Geometry of OH-Functionalized Chiral N-Heterocyclic Carbenes.
Article in Langmuir : the ACS journal of surfaces and colloids, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- N-Heterocyclic carbenes on copper: a dynamic and sensitive interplay between surface functionalization and etching.Chemical science · 2026Article
- Seed-mediated synthesis of NHC-stabilised Cu@Au core-shell nanoparticles from an NHC-Au(I) complex.Nanoscale · 2026Article
- Article
- Heterobinuclear Molecular Precursors Direct the Formation of Supported Subnanometer Cu-M Clusters with Tunable Catalytic Behavior.ACS applied materials & interfaces · 2025Article
- Self-Assembled Monolayer of N-Heterocyclic Carbene as a Primer in a Dual-Layer Coating for Corrosion Protection on Iron.Angewandte Chemie (International ed. in English) · 2025Article
- N-Heterocyclic Carbene Monolayers on Metal-Oxide Films: Correlations between Adsorption Mode and Surface Functionality.Langmuir : the ACS journal of surfaces and colloids · 2024Article
- Nanoimaging of Facet-Dependent Adsorption, Diffusion, and Reactivity of Surface Ligands on Au Nanocrystals.Nano letters · 2023Article
- The influence of adsorption geometry on the reduction affinity of nitroaromatics on Au(111).Physical chemistry chemical physics : PCCP · 2022Article
- N-Heterocyclic Carbene Based Nanolayer for Copper Film Oxidation Mitigation.Angewandte Chemie (International ed. in English) · 2022Article
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10 authors.
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Abstract
Adsorption of chiral molecules on heterogeneous catalysts is a simple approach for inducing an asymmetric environment to enable enantioselective reactivity. Although the concept of chiral induction is straightforward, its practical utilization is far from simple, and only a few examples toward the successful chiral induction by surface anchoring of asymmetric modifiers have been demonstrated so far. Elucidating the factors that lead to successful chiral induction is therefore a crucial step for understanding the mechanism by which chirality is transferred. Herein, we identify the adsorption geometry of OH-functionalized N-heterocyclic carbenes (NHCs), which are chemical analogues to chiral modifiers that successfully promoted α-arylation reactions once anchored on Pd nanoparticles. Polarized near-edge X-ray absorption fine structure (NEXAFS) measurements on Pd(111) revealed that NHCs that were associated with low enantioselectivity were characterized with a well-ordered structure, in which the imidazole ring was vertically positioned and the OH-functionalized side arms were flat-lying. OH-functionalized NHCs that were associated with high enantioselectivity revealed a disordered/flexible adsorption geometry, which potentially enabled better interaction between the OH group and the prochiral reactant.
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