Nanoscale insights in the creation and transfer of chirality in amino acid monolayers at defined metal surfaces

Current Opinion in Colloid and Interface Science

Volumn 13, Issue 1-2, 2008, Pages 65-73

  Barlow, S M ^a   Raval, R ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Chirality; Surfaces

Indexed keywords

ADSORPTION; AMINO ACIDS; BIOMOLECULES; BIOPOLYMERS; CELL IMMOBILIZATION; MONOLAYERS;

DIPEPTIDE ADSORPTION; METAL SURFACES; NANOSCALE INSIGHTS;

CHIRALITY;

AMINO ACID; BIOPOLYMER; DIPEPTIDE; METAL; NANOMATERIAL;

ADSORPTION; CHIRALITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NANOANALYSIS; REVIEW; SURFACE PROPERTY; THERMODYNAMICS;

EID: 37249093950     PISSN: 13590294     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cocis.2007.08.006     Document Type: Review

References (39)

1. Barlow S.M., and Raval R. Complex organic molecules at metal surfaces: bonding, organisation and chirality. Surf Sci Rep 50 (2003) 201-341. A comprehensive review of the adsorption of complex organic molecules at metal surfaces together with a classification of various chiral systems.
2. Barlow S.M., Louafi S., Le Roux D., Williams J., Muryn C., Haq S., et al. Polymorphism in supramolecular chiral structures of R- and S-alanine on Cu(110). Surf Sci 590 (2005) 243-263. The first detailed study of the various local and supramolecular adsorption structures created by the simplest chiral amino acid on an achiral metal surface with particular reference to the polymorphic nature of the organisational behaviour.
3. Raval R. Chiral expression at metal surfaces. Curr Opin Solid State Mater Sci 7 (2003) 67-74
4. Kühnle A., Linderoth T.R., and Besenbacher F. Self-assembly of monodispersed, chiral nanoclusters of cysteine on the Au(110)-(1 × 2) surface. J Am Chem Soc 125 (2003) 14680-14681. STM study showing the formation of local chiral clusters.
5. Humblot V., Methivier C., and Pradier C.-M. Adsorption of l-lysine on Cu(110): a RAIRS study from UHV to the liquid phase. Langmuir 22 (2006) 3089-3096
6. Humblot V., Methivier C., Raval R., and Pradier C.-M. Amino acid and peptides on Cu(110) surfaces: chemical and structural analyses of l-lysine. Surf Sci (May 4 2007) on-line from
7. Jones T.E., and Baddeley C.J. Molecular ordering and adsorbate induced faceting in the Ag{110}-S-glutamic acid system. Langmuir 21 (2005) 9468-9475
8. Jones T.E., Urquhart M.E., and Baddeley C.J. An investigation of the influence of temperature on the adsorption of the chiral modifier, (S)-glutamic acid, on Ni{111}. Surf Sci 587 (2005) 69-77
9. Williams J., Haq S., and Raval R. Surf Sci 368 (1996) 303
10. Barlow S.M., Louafi S., Le Roux D., Williams J., Muryn C., Haq S., et al. Supramolecular assembly of strongly chemisorbed size- and shape-defined chiral clusters: S- and R-alanine on Cu(110). Langmuir 20 (2004) 7171-7176. The first example of a system that forms both chiral clusters and a single chiral domain.
11. Booth N.A., Woodruff D.P., Schaff O., Giessel T., Lindsay R., Baumngartel P., et al. Determination of the local structure of glycine adsorbed on Cu(110). Surf Sci 397 (1998) 258-269
12. Hasselstrom J., Karis O., Weinelt M., Wassdahl N., Nilsson A., Nyberg M., et al. The adsorption structure of glycine adsorbed upon Cu(110); comparison with formate and acetate/Cu(110). Surf Sci 407 (1998) 221-236
13. Kang J.H., Toomes R.L., Polcik M., Kittel M., Hoeft J.T., Efstathiou V., et al. Structural investigation of glycine on Cu(100) and comparison to glycine on Cu(110). J Chem Phys 118 (2003) 6059-6071
14. Nyberg M., Hasselstrom J., Karis O., Wasdahl N., Weinelt M., Nilsson A., et al. The electronic structure and surface chemistry of glycine adsorbed on Cu(110). J Chem Phys 112 (2000) 5420-5427
15. Nyberg M., Odelius M., Nilsson A., and Pettersson L.G.M. Hydrogen bonding between adsorbed deprotonated glycine molecules on Cu(110). J Chem Phys 119 (2003) 12577-12585
16. Jones G., Jones L.B., Thibault-Starzyk F., Seddon E.A., Raval R., Jenkins S.J., et al. The local adsorption geometry and electronic structure of alanine on Cu{110}. Surf Sci 600 (2006) 1924-1935
17. Rankin R.B., and Sholl D.S. Assessment of heterochiral and homochiral glycine adlayers on Cu(110) using density functional theory. Surf Sci 548 (2004) 301-308
18. Rankin R.B., and Sholl D.S. Structures of glycine, enantiopure alanine, and racemic alanine adlayers on Cu(110) and Cu(100) surfaces. J Phys Chem B 109 (2005) 16764-16773. A highly comprehensive study of dense adlayers of amino acids at copper surfaces using Density Functional Theory. Systems with homo and heterochiral adsorption footprints are compared and the energetically preferred structures determined.
19. Rankin R.B., and Sholl D.S. Structure of enantiopure and racemic alanine adlayers on Cu(110). Surf Sci 574 (2005) L1-L8
20. Sayago D.I., Polcik M., Nisbet G., Lamont C.L.A., and Woodruff D.P. Local structure determination of a chiral adsorbate: alanine on Cu(110). Surf Sci 590 (2005) 76-87
21. Barlow S.M., Kitching K.J., Haq S., and Richardson N.V. A study of glycine adsorption on a Cu{110} surface using reflection absorption infrared spectroscopy. Surf Sci 401 (1998) 322
22. Chen Q., Frankel D.J., and Richardson N.V. Chemisorption induced chirality: glycine on Cu{110}. Surf Sci 497 (2002) 37-46
23. Toomes R.L., Kang J.H., Woodruff D.P., Polcik M., Kittel M., and Hoeft J.T. Can glycine form homochiral structural domains on low-index copper surfaces?. Surf Sci 522 (2003) L9
24. Haq S., Massey A., Moslemzadeh N., Robin A., Barlow S.M., and Raval R. Racemic versus enantiopure alanine on Cu(110): an experimental study. Langmuir 23 (2007) 10694-10700
25. Zhao X., Gai Z., Zhao R.G., Yang W.S., and Sakurai T. Adsorption of glycine on Cu(001) and related step faceting and bunching. Surf Sci 424 (1999) L347-L351
26. Zhao X., Zhao R.G., and Yang W.S. Adsorption of alanine on Cu(001) studied by scanning tunneling microscopy. Surf Sci 442 (1999) L995-L1000
27. Iwai H., Tobisawa M., Emori A., and Egawa C. STM study of d-alanine adsorption on Cu(001). Surf Sci 574 (2005) 214-218
28. Mae K., and Morikawa Y. Stability of homochiral and heterochiral phases of glycinate on Cu(0 0 1): a first principles theoretical study. Surf Sci 553 (2004) L63
29. Mateo Marti E., Barlow S.M., Haq S., and Raval R. Bonding and assembly of the chiral amino acid S-proline on Cu(110): the influence of structural sensitivity. Surf Sci 501 (2002) 191-202
30. Kühnle A., Linderoth T.R., Hammer B., and Besenbacher F. Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy. Nature 415 (2002) 891-893. STM images that provided the first evidence of two-dimensional chiral recognition.
31. Lingenfelder M., Tomba G., Constantini G., Ciachchi L.C., De Vita A., and Kern K. Tracking the chiral recognition of adsorbed dipeptides at the single-molecule level. Angew Chem Int Ed 46 (2007) 4492-4495. An important paper using STM imaging and DFT theory that demonstrates that chiral recognition at a surface is a dynamic process.
32. Kühnle A., Linderoth T.R., and Besenbacher F. Enantiospecific adsorption of cysteine at chiral kink sites on Au(110)-(1 × 2). J Am Chem Soc 128 (2006) 1076-1077
33. Greber T., Sljivancanin Z., Schillinger R., Wider J., and Hammer B. Chiral recognition or organic molecules by atomic kinks on surfaces. Phys Rev Lett 96 (2006) 056103-056101-056104. X-ray photoelectron diffraction measurements and DFT calculations showing chiral heterorecognition on the adsorption of cysteine to a vicinal Au(111) surface.
34. Schillinger R., Sljivancanin Z., Hammer B., and Greber T. Probing enantioselectivity with X-ray photoelectron spectroscopy and density functional theory. Phys Rev Lett 98 (2007) 136102-136101-136104
35. Zhao X., Zhao R.G., and Yang W.S. Scanning tunneling microscopy investigation of l-lysine adsorbed on Cu(001). Langmuir 16 (2000) 9812-9818
36. Zhao X. Fabricating homochiral facets on Cu(001) with l-lysine. J Am Chem Soc 122 (2000) 12584-12585. STM demonstration of severe faceting upon adsorption, which is constrained to creating facets of one chirality only.
37. McFadden C.F., Cremer P.S., and Gellman A.J. Langmuir 12 (1996)
38. Rankin R.B., and Sholl D.S. First-principles studies of chiral step reconstructions of Cu(100) by adsorbed glycine and alanine. J Chem Phys 124 (2006) 074703-074701-074706
39. Rankin R.B., and Sholl D.S. Structures of dense glycine and alanine adlayers on chiral Cu(3,1,17) surfaces. Langmuir 22 (2006) 8096-8103