Skip to main content
SpringerLink
Log in

Chirality in Amino Acid Overlayers on Cu Surfaces

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

Abstract

Chirality at surfaces has become a strong focus within the surface science community. A particular motivation is the prospect of using heterogeneous catalysis over chiral solid surfaces for asymmetric synthesis, a prospect which has clear relevance to the pharmaceutical industry. Small amino acids adsorbed on Cu surfaces have emerged as important model systems for studying the interaction of chiral molecules with metal surfaces. In this article, we review the current state of knowledge of these systems, and present the results of new experimental studies of alanine overlayers on Cu{311} and {531} surfaces. Our work on Cu{311} helps us to understand the interplay between different manifestations of chirality, especially “footprint chirality”, in the overlayers. Cu{531} is an intrinsically chiral surface orientation; our data reveal strongly enantiospecific alanine-induced restructuring of this surface. This points the way towards a promising route for obtaining strongly enantiospecific interactions with chiral adsorbates.

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
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  2. Hazen RM, Sholl D (2003) Nat Mater 2:367

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  4. Sholl DS, Gellman AJ (2009) AIChE J 55:2484

    Article  CAS  Google Scholar 

  5. Gellman AJ (2010) ACS Nano 4:5

    Article  CAS  Google Scholar 

  6. Heitbaum M, Glorius F, Escher I (2006) Angew Chem Int Ed 45:4732

    Article  CAS  Google Scholar 

  7. Mallat T, Orglmeister E, Baiker A (2007) Chem Rev 107:4863

    Article  CAS  Google Scholar 

  8. Attard G, Ahmadi A, Feliu J, Rodes A, Herrero E, Blais S, Jerkiewicz G (1999) J Phys Chem B 103:1381

    Article  CAS  Google Scholar 

  9. Ahmadi A, Attard G, Feliu J, Rodes A (1999) Langmuir 15:2420

    Article  CAS  Google Scholar 

  10. Attard GA (2001) J Phys Chem B 105:3158

    Article  CAS  Google Scholar 

  11. Horvath JD, Gellman AJ (2001) J Am Chem Soc 123:7953

    Article  CAS  Google Scholar 

  12. Horvath JD, Gellman AJ (2002) J Am Chem Soc 124:2384

    Article  CAS  Google Scholar 

  13. Horvath JD, Koritnik A, Kamakoti P, Sholl DS, Gellman AJ (2004) J Am Chem Soc 126:14988

    Article  CAS  Google Scholar 

  14. Rampulla DM, Francis AJ, Knight KS, Gellman AJ (2006) J Phys Chem B 110:10411

    Article  CAS  Google Scholar 

  15. Huang Y, Gellman AJ (2008) Catal Lett 125:177

    Article  CAS  Google Scholar 

  16. Woodruff DP, Delchar TA (1994) Modern techniques of surface science, 2nd edn. Cambridge University Press, Cambridge

    Book  Google Scholar 

  17. Koch W, Holthausen MC (2001) A chemist’s guide to density functional theory, 2nd edn. Wiley, Hoboken

    Book  Google Scholar 

  18. Sholl DS, Steckel JA (2009) Density functional theory: a practical introduction. Wiley, Hoboken

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  21. Booth NA, Woodruff DP, Schaff O, Gießel T, Lindsay R, Baumgärtel P, Bradshaw AM (1998) Surf Sci 397:258

    Article  CAS  Google Scholar 

  22. Hasselström J, Karis O, Weinelt M, Wassdahl N, Nilsson A, Nyberg M, Pettersson LGM, Samant MG, Stöhr J (1998) Surf Sci 407:221

    Article  Google Scholar 

  23. Nyberg M, Hasselström J, Karis O, Wassdahl N, Weinelt M, Nilsson A, Pettersson LGM (2000) J Chem Phys 112:5420

    Article  CAS  Google Scholar 

  24. 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 

  25. Nyberg M, Odelius M, Nilsson A, Pettersson LGM (2003) J Chem Phys 119:12577

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  28. Chen Q, Frankel DJ, Richardson NV (2002) Surf Sci 497:37

    Article  CAS  Google Scholar 

  29. Toomes RL, Kang J-H, Woodruff DP, Polcik M, Kittel M, Hoeft J-T (2003) Surf Sci 522:L9

    Article  CAS  Google Scholar 

  30. Jones G, Jenkins SJ, King DA (2006) Surf Sci 600:L224

    Article  CAS  Google Scholar 

  31. Holland BW, Woodruff DP (1973) Surf Sci 36:488

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  34. Rankin RB, Sholl DS (2005) Surf Sci 574:L1

    Article  CAS  Google Scholar 

  35. Sayago DI, Polcik M, Nisbet G, Lamont CLA, Woodruff DP (2005) Surf Sci 590:76

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  41. Zhao X, Wang H, Zhao RG, Yang WS (2001) Mater Sci Eng C 16:41

    Article  Google Scholar 

  42. Zhao X, Gai Z, Zhao RG, Yang WS, Sakurai T (1999) Surf Sci 424:L347

    Article  CAS  Google Scholar 

  43. Zhao X, Zhao RG, Yang WS (1999) Surf Sci 442:L995

    Article  CAS  Google Scholar 

  44. Efstathiou V, Woodruff DP (2003) Surf Sci 531:304

    Article  CAS  Google Scholar 

  45. Mae K, Morikawa Y (2004) Surf Sci 553:L63

    Article  CAS  Google Scholar 

  46. Egawa C, Iwai H, Kabutoya M, Oki S (2003) Surf Sci 532–535:233

    Article  Google Scholar 

  47. Iwai H, Tobisawa M, Emori A, Egawa C (2005) Surf Sci 574:214

    Article  CAS  Google Scholar 

  48. Iwai H, Egawa C (2010) Langmuir 26:2294

    Article  CAS  Google Scholar 

  49. Rankin RB, Sholl DS (2006) J Chem Phys 124:074703

    Article  Google Scholar 

  50. Rankin RB, Sholl DS (2006) Langmuir 22:8096

    Article  CAS  Google Scholar 

  51. Jenkins SJ, Pratt SJ (2007) Surf Sci Rep 62:373

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  53. Sholl DS (1998) Langmuir 14:862

    Article  CAS  Google Scholar 

  54. Sholl DS, Asthagiri A, Power TD (2001) J Phys Chem B 105:4771

    Article  CAS  Google Scholar 

  55. Power TD, Asthagiri A, Sholl DS (2002) Langmuir 18:3737

    Article  CAS  Google Scholar 

  56. Asthagiri A, Feibelman PJ, Sholl DS (2002) Top Catal 19:193

    Article  Google Scholar 

  57. Baber AE, Gellman AJ, Sholl DS, Sykes ECH (2008) J Phys Chem C 112:11086

    Article  CAS  Google Scholar 

  58. Eralp T, Shavorskiy A, Zheleva ZV, Dhanak VR, Held G (2010) Langmuir 26:10918

    Article  CAS  Google Scholar 

  59. Gladys MJ, Stevens AV, Scott NR, Jones G, Batchelor D, Held G (2007) J Phys Chem C 111:8331

    Article  CAS  Google Scholar 

  60. Thomsen L, Wharmby MT, Riley DP, Held G, Gladys MJ (2009) Surf Sci 603:1253

    Article  CAS  Google Scholar 

  61. Titmuss S (1999) A new approach to surface structure determination by low energy diffraction. PhD thesis. University of Cambridge, Cambridge

  62. Driver SM, King DA (2007) Surf Sci 601:510

    Article  CAS  Google Scholar 

  63. Kose R, King DA (1999) Chem Phys Lett 1–2:1

    Article  Google Scholar 

  64. Clegg ML, Driver SM, Blanco-Rey M, King DA (2010) J Phys Chem C 114:4114

    Article  CAS  Google Scholar 

  65. Puisto SR, Held G, King DA (2005) Phys Rev Lett 95:036102

    Article  CAS  Google Scholar 

  66. Puisto SR, Held G, Ranea V, Jenkins SJ, Mola EE, King DA (2005) J Phys Chem B 109:22456

    Article  CAS  Google Scholar 

  67. Houston JE, Park RL (1971) Surf Sci 26:269

    Article  CAS  Google Scholar 

  68. Laramore GE, Houston JE, Park RL (1973) J Vac Sci Technol 10:196

    Article  CAS  Google Scholar 

  69. Cowley JM, Shuman H (1973) Surf Sci 28:53

    Article  Google Scholar 

  70. Zhao X, Perry SS (2004) J Mol Catal A 216:257

    Article  CAS  Google Scholar 

  71. Giesen M, Dieluweit S (2004) J Mol Catal A 216:263

    Article  CAS  Google Scholar 

  72. Green MM, Reidy MP, Johnson RJ, Darling G, O’Leary DJ, Wilson G (1989) J Am Chem Soc 111:6452

    Article  Google Scholar 

  73. Wintterlin J, Schuster R, Coulman DJ, Ertl G, Behm RJ (1991) J Vac Sci Technol B 9:902

    Article  CAS  Google Scholar 

  74. Voet D, Voet JG (2004) Biochemisty, 3rd edn. Wiley, Hoboken

    Google Scholar 

Download references

Acknowledgments

The authors thank Dr. M. Blanco Rey, Prof. R. Raval and Drs. A. Mark, M. Forster and S. J. Jenkins for valuable discussions. The EPSRC is acknowledged for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK

    Marian L. Clegg, Sofia Karakatsani, David A. King & Stephen M. Driver

  2. Centro de Nanociencias y Nanotecnologia, Universidad Nacional Autonoma de Mexico, Apdo. Postal 356, Ensenada, 22800, Baja California, Mexico

    Leonardo Morales de la Garza

Authors
  1. Marian L. Clegg
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Leonardo Morales de la Garza
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sofia Karakatsani
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. David A. King
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Stephen M. Driver
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Stephen M. Driver.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Clegg, M.L., Morales de la Garza, L., Karakatsani, S. et al. Chirality in Amino Acid Overlayers on Cu Surfaces. Top Catal 54, 1429–1444 (2011). https://doi.org/10.1007/s11244-011-9758-y

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-011-9758-y

Keywords

Search

Navigation