Emerging Solvent‐Induced Homochirality by the Confinement of Achiral Molecules Against a Solid Surface

Katsonis, Nathalie; Xu, Hong; Haak, Robert M.; Kudernác, Tibor; Tomović, Željko; George, Subi J.; Auweraer, Mark Van der; Schenning, Albert P. H. J.; Meijer, E. W.; Feringa, Ben L.; Feyter, Steven De

doi:10.1002/anie.200800255

Cited by 95 publications

(67 citation statements)

References 39 publications

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“…Using chiral solvents, excess of CW or CCW pinwheels in monolayers of achiral oligophenylene derivatives, similar to those shown in Fig. 19, was reported [164]. Using these achiral oligophenylenes and dibenzoyl tartaric acid as chiral auxiliaries in the achiral solvent, the same effect was observed [165].…”

Section: Diastereomers and Diastereomeric Recognitionsupporting

confidence: 70%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

223

264

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With the adsorption of larger molecules being increasingly tackled by surface scientists, the aspect of chirality often plays a role. This paper gives a topical review of molecular chirality at surfaces and gives a phenomenological overview of different aspects of adsorption and self‐assembly of chiral and prochiral molecules and the principles of mirror‐symmetry breaking at a surface. After a brief introduction into the history of molecular chirality and the important role it played for understanding the spatial structure of molecules, definitions of chirality are presented. Topics treated here are principle ways to create single chiral adsorbates, chiral ensembles, and monolayers by achiral molecules, adsorption of intrinsically chiral molecules at achiral and chiral surfaces, long‐range symmetry breaking in two‐dimensional (2D) crystals due to additional chiral bias, chiral restructuring of solid surfaces under the influence of chiral molecules, switching the handedness of adsorbates, and chirality at the liquid/air interface. An outlook onto further potential research directions and recommendations for further reading, including nonsurface‐related sources of chiral topics completes this paper.

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Section: Diastereomers and Diastereomeric Recognitionsupporting

confidence: 70%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

223

264

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“…Finally, the formation of global homochirality assembly of BIC is supposed to be related to the strong supramolecular interactions between BIC aggregates and chiral 2-octanol, as well as the participation of the co-absorber in the assembly process. De Feyter’s group reported the chiral solvent and chiral auxiliary-biased formation of 2D enantiomeric assembly of achiral molecules2936, although with relatively low ee. Coincidently, the chiral solvent or chiral auxiliary is not indispensible for the formation of the assembly.…”

Section: Discussionmentioning

confidence: 99%

“…However, the nonlinear chirality amplification in molecular assemblies on solid surfaces consisting of achiral molecules has not been demonstrated. In addition, few examples have shown that 2D homochirality can be achieved by external means such as magnetic field and chiral solvent3233343536. For example, De Feyter et al have shown that the formation of 2D molecular rosettes can be biased towards being either right-handed or left-handed by using a chiral solvent36.…”

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confidence: 99%

Globally homochiral assembly of two-dimensional molecular networks triggered by co-absorbers

et al. 2013

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Understanding the chirality induction and amplification processes, and the construction of globally homochiral surfaces, represent essential challenges in surface chirality studies. Here we report the induction of global homochirality in two-dimensional enantiomorphous networks of achiral molecules via co-assembly with chiral co-absorbers. The scanning tunnelling microscopy investigations and molecular mechanics simulations demonstrate that the point chirality of the co-absorbers transfers to organizational chirality of the assembly units via enantioselective supramolecular interactions, and is then hierarchically amplified to the global homochirality of two-dimensional networks. The global homochirality of the network assembly shows nonlinear dependence on the enantiomeric excess of chiral co-absorber in the solution phase, demonstrating, for the first time, the validation of the ‘majority rules’ for the homochirality control of achiral molecules at the liquid/solid interface. Such an induction and nonlinear chirality amplification effect promises a new approach towards two-dimensional homochirality control and may reveal important insights into asymmetric heterogeneous catalysis, chiral separation and chiral crystallization.

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“…the ability to steer the chirality of molecules or assemblies towards one specific handedness, have been performed [42,43]. Chiral symmetry on surfaces may be broken by the use of external agents in the form of a chiral solvent [44] or a magnetic field [45]. A related approach is the ''sergeants and soldiers'' effect where a homochiral seed induces a chiral response in target molecules as has been demonstrated in surface assemblies in a couple of instances [46][47][48].…”

Section: Introductionmentioning

confidence: 99%

Chiral Symmetry Breaking Observed for Cysteine on the Au(110)-(1×2) Surface

2011

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A pronounced enantiomeric excess of LL-cysteine dimers is observed by scanning tunneling microscopy (STM) on the Au (110)- (192) surface after partial thermal desorption/decomposition of racemic cysteine. We systematically examine several possible origins for this intriguing observation of chiral symmetry breaking, including a chiral bias of the substrate, but remain unable to identify the source.

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Emerging Solvent‐Induced Homochirality by the Confinement of Achiral Molecules Against a Solid Surface

Cited by 95 publications

References 39 publications

Molecular chirality at surfaces

Molecular chirality at surfaces

Globally homochiral assembly of two-dimensional molecular networks triggered by co-absorbers

Chiral Symmetry Breaking Observed for Cysteine on the Au(110)-(1×2) Surface

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