Skip to main content
SpringerLink
Log in

Assembly of Chiral Amino-Acids at Surfaces from a Single Molecule Perspective: Proline on Cu(110)

  • Original Paper
  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

We present a molecule-by-molecule mapping of an amino-acid monolayer on a Cu(110) surface in which individual molecular configuration, bonding and adsorption footprints are identified. This detailed mapping provides direct evidence that the (4 × 2) structures of enantiopure and racemic proline are governed by a strict heterochiral adsorption footprint template. For the racemic system this has an interesting consequence, namely that it leads to a 2-D random solid solution, a situation that is rarely encountered in 3-D.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Sheldon RA (1993) Industrial synthesis of optically active compounds. Chirotechnology Dekker, New York

  2. Dubois V, Jannes G (eds) (1995) Chiral reactions in heterogeneous catalysis. Plenum, New York, p. 33

  3. Baiker A, Blaser HU (1997) In: Ertl GH, Knoezinger H, Weinheim J (eds) Handbook of heterogeneous catalysis, vol 5. VHC, New York, p 2442

  4. McFadden CF, Cremer PS, Gellman AJ (1996) Langmuir 12:2483

    Article  CAS  Google Scholar 

  5. Besson M, Debleqc F, Gallezot P, Neto S, Pinel C (2000) Chem Eur J 6:949

    Article  CAS  Google Scholar 

  6. Izumi Y (1983) Adv Catal 32:215

    Article  CAS  Google Scholar 

  7. Tai A, Harada T (1986) Asymmetrically modified nickel catalysts. In: Iwasawa Y (ed) Tailored metal catalysts, Reidel, Tokyo, p 265

  8. Orito Y, Imai S, Niwa S (1980) J Chem Soc Jpn 670

  9. Webb G, Wells PB (1992) Catal Today 12:319

    Article  CAS  Google Scholar 

  10. Blaser HU, Jalett HP, Muller M, Studer M (1997) Catal Today 37:441

    Article  CAS  Google Scholar 

  11. Tungler A, Kajtar M, Mathe T, Toth G, Fogassy E, Petro J (1989) Catal Today 5:159

    Article  CAS  Google Scholar 

  12. Baiker A (1997) J Mol Catal A 115:473

    Article  CAS  Google Scholar 

  13. Wells PB, Wilkinson AG (1998) Top Catal 5:39

    Article  CAS  Google Scholar 

  14. Besson M, Blanc B, Champelet M, Gallezot P, Nasar K, Pinel C (1997) J Catal 170:254

    Article  CAS  Google Scholar 

  15. Ranade VS, Consilglio G, Prins R (1999) Catal Lett 58:71

    Article  CAS  Google Scholar 

  16. Tungler A, Mathe T, Petro J, Tarnai T (1990) J Mol Catal A 61:259

    Article  CAS  Google Scholar 

  17. McIntosh AI, Watson DJ, Burton JW, Lambert RM (2006) J Am Chem Soc 128:7329

    Article  CAS  Google Scholar 

  18. Raval R (2001) Cattech 5:1

    Article  Google Scholar 

  19. Ma Z, Zaera F (2007) In: Ozkan US (ed) Design of heterogeneous catalysis: new approaches based on synthesis, characterization, and modelling, Wiley-VCH, Weinheim

  20. Tysoe WT (2007) Nanotoday 2:53

    Google Scholar 

  21. Raval R (2009) Chem Soc Rev 38:707

    Article  CAS  Google Scholar 

  22. Perez-Garcia L, Amabilino DB (2007) Chem Soc Rev 36:941

    Article  CAS  Google Scholar 

  23. Barlow SM, Raval R (2003) Surf Sci Rep 50:201

    Article  CAS  Google Scholar 

  24. Ernst K-H (2006) Supramolecular surface chirality. Top Curr Chem 265:209

    Article  CAS  Google Scholar 

  25. Barlow SM, Raval R (2008) Curr Opin Colloid Inter Sci 13:65

    Article  CAS  Google Scholar 

  26. Humblot V, Barlow SM, Raval R (2004) Prog Surf Sci 76:1

    Article  CAS  Google Scholar 

  27. Forster M, Raval R (2009) Chiral expression by organic architectures at metal surfaces: the role of both adsorbate and surface in inducing asymmetry. In Rioux R (ed) Model systems in catalysis: single crystals to supported enzyme mimics, Springer, New York, p 97

  28. Forster M, Dyer MS, Persson M, Raval R (2009) J Am Chem Soc 131:10173

    Article  CAS  Google Scholar 

  29. Forster M, Dyer MS, Persson M, Raval R (2010) Angew Chem Int Ed 49:2344

    CAS  Google Scholar 

  30. Mateo Marti E, Barlow SM, Haq S, Raval R (2002) Surf Sci 501:191

    Article  CAS  Google Scholar 

  31. Rankin RB, Sholl DS (2005) J Phys Chem B 109:16764

    Article  CAS  Google Scholar 

  32. Rankin RB, Sholl DS (2004) Surf Sci 548:301

    Article  CAS  Google Scholar 

  33. Jones G, Jones LB, Thibault-Starzyk F, Seddon EA, Raval R, Jenkins SJ, Held G (2006) Surf Sci 600:1924

    Article  CAS  Google Scholar 

  34. Barlow SM, Louafi S, Le Roux D, Williams J, Muryn C, Haq S, Raval R (2005) Surf Sci 590:243

    Article  CAS  Google Scholar 

  35. Barlow SM, Louafi S, LeRoux D, Williams J, Muryn C, Haq S, Raval R (2004) Langmuir 20:7171

    Article  CAS  Google Scholar 

  36. Haq S, Massey A, Moslemzadeh N, Robin A, Barlow SM, Raval R (2007) Langmuir 23:10694

    Article  CAS  Google Scholar 

  37. Williams J, Haq S, Raval R (1996) Surf Sci 368:303

    Article  CAS  Google Scholar 

  38. Barlow SM, Kitching KJ, Haq S, Richardson NV (1998) Surf Sci 401:322

    Article  CAS  Google Scholar 

  39. Booth NA, Woodruff DP, Schaff O, Giessel T, Lindsay R, Baumgartel P, Bradshaw AM (1998) Surf Sci 397:258

    Article  CAS  Google Scholar 

  40. Kang J-H, Toomes RL, Polcik M, Kittel M, Hoeft J-T, Efstathiou V, Woodruff DP, Bradshaw AM (2003) J Chem Phys 118:6059

    Article  CAS  Google Scholar 

  41. Unac RC, GilRabaza AV, Vidales AM, Zgrablich G (2007) App Surf Sci 254:125

    Article  CAS  Google Scholar 

  42. Lopez RH, Roma F, Gargiulo V, Sales JL, Zgrablich G (2008) J Phys Chem B 112:8619

    Article  CAS  Google Scholar 

Download references

Acknowledgments

R.R and M.F acknowledge the Engineering and Physical Sciences Research Council (EPSRC), EU seventh framework small scale collaborative project RESOLVE (NMP4-SL-2008-214340) and the University of Liverpool for equipment grants, funding and a studentship for M.F. M.P acknowledges the Swedish Research Council (VR) and the Marie Curie Research Training Network PRAIRIES, contract MRTN-CT-2006-035810. M.S.D acknowledges the University of Liverpool for funding of a postdoctoral fellowship and computational resources.

Author information

Authors and Affiliations

  1. Surface Science Research Centre and Department of Chemistry, University of Liverpool, Liverpool, L69 3BX, UK

    M. Forster, M. S. Dyer, M. Persson & R. Raval

  2. Department of Applied Physics, Chalmers University of Technology, SE-412 96, Göteborg, Sweden

    M. Persson

Authors
  1. M. Forster
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. S. Dyer
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Persson
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. Raval
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. Raval.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Forster, M., Dyer, M.S., Persson, M. et al. Assembly of Chiral Amino-Acids at Surfaces from a Single Molecule Perspective: Proline on Cu(110). Top Catal 54, 13–19 (2011). https://doi.org/10.1007/s11244-011-9634-9

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-011-9634-9

Keywords

Search

Navigation