Chiral surfaces: Accomplishments and challenges

ACS Nano

Volumn 4, Issue 1, 2010, Pages 5-10

  Gellman, Andrew J ^a,b  

^a CARNEGIE MELLON UNIVERSITY   (United States)

^b NATIONAL ENERGY TECHNOLOGY LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORBED SPECIES; CHEMICAL PROCESS; CHIRAL METAL SURFACES; CHIRAL MOLECULE; CHIRAL SURFACE; ENANTIOSELECTIVE; ENANTIOSPECIFIC; INTERMOLECULAR INTERACTIONS; MOLECULAR LEVELS; TEMPLATED; TEMPLATING;

ADSORPTION; ELECTRON TRANSITIONS; STEREOCHEMISTRY; SURFACE CHEMISTRY;

ENANTIOSELECTIVITY;

EID: 75749095618     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn901885n     Document Type: Review

References (34)

1. Pirkle, W. H.; Finn, J. M.; Schreiner, J. L.; Hamper, B. C. A Widely Useful Chiral Stationary Phase for the High-Performance Liquid-Chromatography Separation of Enantiomers. J. Am. Chem. Soc. 1981, 103, 3964-3966.
2. Orito, Y.; Niwa, S.; Imai, S. Asymmetric Hydrogenation of Methyl Acetoacetate Using Nickel-Platinum Metal-Kieselguhr Catalysts Modified with Tartaric Acid. J. Synth. Org. Chem. Jpn. 1976, 34, 236-239.
3. Blaser, H. U. Heterogeneous Catalysis for Fine Chemicals Production. Catal. Today 2000, 60, 161-165.
4. Mallat, T.; Orglmeister, E.; Baiker, A. Asymmetric Catalysis at Chiral Metal Surfaces. Chem. Rev. 2007, 107, 4863-4890.
5. Hazen, R. M.; Sholl, D. S. Chiral Selection on Inorganic Crystalline Surfaces. Nat. Mater. 2003, 2, 367-374.
6. Kuhnle, A.; Linderoth, T. R.; Hammer, B.; Besenbacher, F. Chiral Recognition in Dimerization of Adsorbed Cysteine Observed by Scanning Tunnelling Microscopy. Nature 2002, 415, 891-893.
7. Kuhnle, A.; Linderoth, T. R.; Besenbacher, F. Self-Assembly of Monodispersed, Chiral Nanoclusters of Cysteine on the Au(110)-(1 × 2) Surface. J. Am. Chem. Soc. 2003, 125, 14680-14681.
8. Ernst, K. H. In Supramolecular Chirality; Crego-Calama, M., Reinhoudt, D. N., Eds.; Springer-Verlag GmbH: Heidelberg, Germany, 2006; Vol. 265, pp 209-252.
9. Humblot, V.; Barlow, S. M.; Raval, R. Two-Dimensional Organisational Chirality through Supramolecular Assembly of Molecules at Metal Surfaces. Prog. Surf. Sci. 2004, 76, 1-19.
10. Bombis, C.; Weigelt, S.; Knudsen, M. M.; Nørgaard, M.; Busse, C.; Lægsgaard, E.; Besenbacher, F.; Gothelf, K. V.; Linderoth, T. R. Steering Organizational and Conformational Surface Chirality by Controlling Molecular Chemical Functionality. ACS Nano 2010, 4, 297-311.
11. Lorenzo, M. O.; Baddeley, C. J.; Muryn, C.; Raval, R. Extended Surface Chirality from Supramolecular Assemblies of Adsorbed Chiral Molecules. Nature 2000, 404, 376-378.
12. Forbes, J. G.; Gellman, A. J.; Dunphy, J. C.; Salmeron, M. Imaging of Sulfur Overlayer Structures on the Pd(111) Surface. Surf. Sci. 1992, 279, 68-78.
13. McFadden, C. F.; Cremer, P. S.; Gellman, A. J. Adsorption of Chiral Alcohols on "Chiral" Metal Surfaces. Langmuir 1996, 12, 2483-2487.
14. Jenkins, S. J.; Pratt, S. J. Beyond the Surface Atlas: A Roadmap and Gazetteer for Surface Symmetry and Structure. Surf. Sci. Rep. 2007, 62, 373-429.
15. Sholl, D. S.; Asthagiri, A.; Power, T. D. Naturally Chiral Metal Surfaces as Enantiospecific Adsorbents. J. Phys. Chem. B 2001, 105, 4771-4782.
16. Baber, A. E.; Gellman, A. J.; Sholl, D. S.; Sykes, E. C. H. The Real Structure of Naturally Chiral Cu{643}. J. Phys. Chem. C 2008, 112, 11086-11089.
17. Kuhnle, A.; Linderoth, T. R.; Besenbacher, F. Enantiospecific Adsorption of Cysteine at Chiral Kink Sites on Au(110)-(1 × 2). J. Am. Chem. Soc. 2006, 128, 1076-1077.
18. Attard, G. A. Electrochemical Studies of Enantioselectivity at Chiral Metal Surfaces. J. Phys. Chem. B 2001, 105, 3158-3167.
19. Ahmadi, A.; Attard, G.; Feliu, J.; Rodes, A. Surface Reactivity at "Chiral" Platinum Surfaces. Langmuir 1999, 15, 2420-2424.
20. Attard, G. A.; Ahmadi, A.; Feliu, J.; Rodes, A.; Herrero, E.; Blais, S.; Jerkiewicz, G. Temperature Effects in the Enantiomeric Electro-Oxidation of D- and L-Glucose on Pt{643}(S). J. Phys. Chem. B 1999, 103, 1381-1385.
21. Horvath, J. D.; Gellman, A. J. Enantiospecific Desorption of Chiral Compounds from Chiral Cu(643) and Achiral Cu(111) Surfaces. J. Am. Chem. Soc. 2002, 124, 2384-2392.
22. Horvath, J.; Kamakoti, P.; Koritnik, A.; Sholl, D. S.; Gellman, A. J. Enantioselective Separation on a Naturally Chiral Surface. J. Am. Chem. Soc. 2004, 126, 14998-14994.
23. Horvath, J. D.; Baker, L.; Gellman, A. J. Enantiospecific Orientation of (R)-3-Methylcyclohexanone on the Chiral Cu(643) (R/S) Surfaces. J. Phys. Chem. C 2008, 112, 7637-7643.
24. Sholl, D. S.; Gellman, A. J. Developing Chiral Surfaces for Enantioselective Chemical Processing. AIChE J. 2009, 55, 2484-2490.
25. Huang, Y.; Gellman, A. J. Enantiospecific Adsorption of (R)-3- Methylcyclohexanone on Naturally Chiral Cu(531) (R&S) Surfaces. Catal. Lett. 2008, 125, 177-182.
26. Rampulla, D. M.; Francis, A. J.; Knight, K. S.; Gellman, A. J. Enantioselective Surface Chemistry of R-2-Bromobutane on Cu(643) (R&S) and Cu(531) (R&S) . J. Phys. Chem. B 2006, 110, 10411-10420.
27. Stacchiola, D.; Burkholder, L.; Tysoe, W. T. Enantioselective Chemisorption on a Chirally Modified Surface in Ultrahigh Vacuum: Adsorption of Propylene Oxide on 2-Butoxide-Covered Palladium(111). J. Am. Chem. Soc. 2002, 124, 8984-8989.
28. Stacchiola, D.; Burkholder, L.; Tysoe, W. T. Probing Enantio Selective Chemisorption in Ultrahigh Vacuum. J. Mol. Catal. A 2004, 216, 215-221.
29. Zaera, F. Regio-, Stereo-, and Enantioselectivity in Hydrocarbon Conversion on Metal Surfaces. Acc. Chem. Res. 2009, 42, 1152-1160.
30. Sholl, D. S.; Steckel, J. A. Density Functional Theory: A Practical Introduction; John Wiley and Sons, Inc.: Hoboken, NJ, 2009.
31. Schunack, M.; Laegsgaard, E.; Stensgaard, I.; Johannsen, I.; Besenbacher, F. A Chiral Metal Surface. Angew. Chem., Int. Ed. 2001, 40, 2623-2626.
32. Zhao, X. Y. Fabricating Homochiral Facets on Cu(001) with L-Lysine. J. Am. Chem. Soc. 2000, 122, 12584-12585.
33. Switzer, J. A.; Kothari, H. M.; Poizot, P.; Nakanishi, S.; Bohannan, E. W. Enantiospecific Electrodeposition of a Chiral Catalyst. Nature 2003, 425, 490-493.
34. 3(621) System. Surf. Sci. 2007, 601, 1930-1936.