Synthesis, Characterization, and Electrochemical Applications of Chiral Imprinted Mesoporous Ni Surfaces

• Published in: Journal of the American Chemical Society Vol. 141; no. 47; pp. 18870 - 18876
• Main Authors: Assavapanumat, Sunpet, Ketkaew, Marisa, Kuhn, Alexander, Wattanakit, Chularat
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 27.11.2019
• Subjects: Catalysis; Chemical Sciences; Material chemistry
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/jacs.9b10507

The enantioselective synthesis of chiral compounds is of crucial importance for a wide range of potential applications, especially in cosmetic and pharmaceutical industries. Recently, chiral imprinted mesoporous platinum films, produced by the electrodeposition of the metal, in the simultaneous presence of a lyotropic liquid crystalline phase of nonionic surfactants as mesoporogens and chiral templates, have been applied as electrocatalysts and selective stationary phases for the asymmetric synthesis and separation of chiral compounds, respectively. However, platinum is an expensive metal, and therefore it is mandatory to explore the possibility to apply this concept also to other metals. In this contribution, we propose mesoporous chiral imprinted nickel as an alternative cheap and earth-abundant metal. The designed surface layers not only demonstrate electrochemical discrimination between two enantiomers, but most importantly also allow stereospecific electroreduction of a prochiral compound, with very significant enantioselectivity of up to 80% ee. These results open up very promising perspectives for the development of low-cost non-noble-metal matrices for the synthesis of chiral compounds.