Chiral imprinting of palladium with cinchona alkaloids

Pachón, Laura Durán; Yosef, Itzik; Markus, Tal Z.; Naaman, Ron; Avnir, David; Rothenberg, Gadi

doi:10.1038/nchem.180

Cited by 92 publications

(52 citation statements)

References 18 publications

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“…With this respect, very interesting approaches have been put forward in the literature, mostly based on the concept of molecular imprinting of polymers (MIPs)21222324 or other materials252627, and some authors could extend the concept even to metals282930. As the matrices obtained by such an imprinting approach have cavities with a shape similar to the used template, this confined reaction space might be used to direct the product formation.…”

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confidence: 99%

Asymmetric synthesis using chiral-encoded metal

et al. 2016

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The synthesis of chiral compounds is of crucial importance in many areas of society and science, including medicine, biology, chemistry, biotechnology and agriculture. Thus, there is a fundamental interest in developing new approaches for the selective production of enantiomers. Here we report the use of mesoporous metal structures with encoded geometric chiral information for inducing asymmetry in the electrochemical synthesis of mandelic acid as a model molecule. The chiral-encoded mesoporous metal, obtained by the electrochemical reduction of platinum salts in the presence of a liquid crystal phase and the chiral template molecule, perfectly retains the chiral information after removal of the template. Starting from a prochiral compound we demonstrate enantiomeric excess of the (R)-enantiomer when using (R)-imprinted electrodes and vice versa for the (S)-imprinted ones. Moreover, changing the amount of chiral cavities in the material allows tuning the enantioselectivity.

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confidence: 99%

Asymmetric synthesis using chiral-encoded metal

et al. 2016

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“…They exhibit moderate enantioselective recognition properties when used for the oxidation of tartrate enantiomers29. To date, the synthesis of such intrinsically chiral metal structures by the imprinting approach is still in an early stage of development3031. Engineering of chiral Pd, Au, Pt and Ag has been reported303132; however, the imprinted chirality could not be used for enantioselective recognition after removal of the template.…”

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Enantioselective recognition at mesoporous chiral metal surfaces

et al. 2014

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Chirality is widespread in natural systems, and artificial reproduction of chiral recognition is a major scientific challenge, especially owing to various potential applications ranging from catalysis to sensing and separation science. In this context, molecular imprinting is a well-known approach for generating materials with enantioselective properties, and it has been successfully employed using polymers. However, it is particularly difficult to synthesize chiral metal matrices by this method. Here we report the fabrication of a chirally imprinted mesoporous metal, obtained by the electrochemical reduction of platinum salts in the presence of a liquid crystal phase and chiral template molecules. The porous platinum retains a chiral character after removal of the template molecules. A matrix obtained in this way exhibits a large active surface area due to its mesoporosity, and also shows a significant discrimination between two enantiomers, when they are probed using such materials as electrodes.

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“…35 In order to improve the surface area, porous chiral metal matrices have been prepared with combination of imprinting technique. 36,37 In a study by Kuhn and co-workers, chiral imprinted porous Pt films were obtained by the electrochemical reduction of Pt salts on gold electrodes. 37 …”

Section: Restructured Achiral Metal Surfacesmentioning

confidence: 99%

Emerging enantiomeric resolution materials with homochiral nano-fabrications

Wang

Wei

2015

Nanoscale

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The major scientific challenge of enantiomeric separation is to develop simple, rapid, and sensitive routine analytical methods. Generally, enantio-resolution is still based on "three-point interaction" theory, which indicates that homochiral sites are needed for enantio-selective interaction. However, in recent years, advanced materials with precise homochiral fabrication at the nanoscale have been synthesized, and have shown great potential in development of high-throughput enantio-resolution methods. This tutorial review summarizes fabrication and applications of homochiral materials for enantio-selective recognition and separation. These materials, which include intrinsic and restructured chiral metal surfaces, plasmonic nanostructures, coordination polymers, organic polymer sensors, and molecularly imprinted polymers, have been applied as sensors or chiral stationary phases (CSPs) for efficient enantio-resolution.

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Chiral imprinting of palladium with cinchona alkaloids

Cited by 92 publications

References 18 publications

Asymmetric synthesis using chiral-encoded metal

Asymmetric synthesis using chiral-encoded metal

Enantioselective recognition at mesoporous chiral metal surfaces

Emerging enantiomeric resolution materials with homochiral nano-fabrications

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