Enantioselectivity on Surfaces

Rampulla, David M.; Gellman, Andrew J.

doi:10.1201/noe0849396397.ch109

Cited by 1 publication

(1 citation statement)

References 29 publications

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“…To separate enantiomers or to direct their stereoselective synthesis chiraly templated surfaces have been recently proposed. Those surfaces comprise a solid support on which chiral modifier molecules are preadsorbed, and due to the 2D self-assembly they form a homochiral matrix able to interact selectively with the complementary guest enantiomers (Zaera 2008;Rampulla and Gellman 2004). In fact, it has been demonstrated in numerous cases that to create homochiral adsorbed structures one does not to have to use chiral modifier-conversely, even achiral molecules have been found to be able to create chiral 2D assemblies (Kudernac et al 2009;Miyake et al 2008;Mu et al 2008).…”

Section: Introductionmentioning

confidence: 99%

Creation of chiral adsorbed structures using external inputs: results from lattice Monte Carlo simulations

Woszczyk

Szabelski

2015

Adsorption

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Patterning of solid surfaces with organic molecules has been recognized as a promising method to create functional 2D matrices with tunable structure and properties. In this work we use the lattice Monte Carlo simulations to study chiral pattern formation in adsorbed systems comprising simple molecular building blocks differing in shape. To that end we consider five-membered rigid isomers whose composite segments can occupy vertices of a triangular lattice and interact with short-range (nearest neighbors) forces. Our main focus is on those molecules which are prochiral, that is they can adopt mirror-image planar configurations when adsorbed. Moreover, the effect of orientational in-plane confinement of the molecules, which reflects their coupling with an external directional field, on the structure formation and chiral resolution in 2D is explored. The obtained results demonstrate that the confinement imposed on the surface enantiomers can induce their resolution and formation of extended homochiral domains. However, it is also shown that for certain molecular shapes the confinement can produce mixed racemic crystals instead of the homochiral assemblies. The insights from our simulation studies can be helpful in preliminary screening of molecular libraries to select optimal building blocks able to self-assembly into chiral 2D patterns with predefined architecture.

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