Skip to main content
SpringerLink
Log in

Supramolecular Surface Chirality

  • Chapter
  • First Online:
Supramolecular Chirality

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 265))

Abstract

Two-dimensional supramolecular chemistry on surfaces is strongly governed by directional forces, and expression of chirality in two dimensions is quite pronounced due to confinement to the plane. In particular the absence of certain symmetry elements has a strong influence on pattern formation. With the appearance of scanning tunneling microscopy, two-dimensional supramolecular chirality has become a popular issue in the field of surface self-assembly during the last decade. By using recent examples from literature, a conceptual overview on different aspects of surface chirality will be given. The main topics are adsorption-induced chirality, chiral recognition, transfer of chirality from single molecules into supramolecular structures, and cooperatively driven chiral amplification phenomena.

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

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

1D:

one-dimensional

2D:

two-dimensional

3D:

three-dimensional

[7]H:

heptahelicene

8CB:

4-cyano-4′-octibiphenyl

AA:

arachidic anhydride

AES:

Auger electron spectroscopy

AFM:

atomic force microscopy

bcc:

body centered cubic

CCW:

counterclockwise

CW:

clockwise

4′:

workfunction change

ee:

enantiomeric excess

fcc:

face-centered cubic

hcp:

hexagonal close-packed

hopg:

highly ordered pyrolytic graphite

HREELS:

high-resolution electron energy loss spectroscopy

ISA:

5-[10-(2-methylbutoxy)decyloxy] isophthalic acid

LC:

liquid crystal

LEED:

low-energy electron diffraction

MAA:

methylacetoacetate

ML:

monolayer

MMC:

molecular modeling calculations

NN:

1-nitronaphtalene

NP:

naphtho[2,3-a] pyrene

PVBA:

4-trans-2-(pyridyl-4-yl-vinyl) benzoic acid

RAIRS:

reflection–absorption infrared spectroscopy

RT:

room temperature

SDA:

4,4′-stilbene dicarboxylic acid

SIMS:

secondary ion mass spectrometry

STM:

scanning tunneling microscopy

SU:

succinic acid

SubPC:

chloro[subphthalocyaninato] boron(ii)

TA:

tartaric acid

TPD:

temperature programmed desorption

UHV:

ultra-high vacuum

XPS, XPD:

X-ray photoelectron spectroscopy, -diffraction

References

  1. Christmann K (1991) Introduction to Surface Physical Chemistry. Springer, Berlin Heidelberg New York (Steinkopf, Darmstadt)

    Google Scholar 

  2. Schipper PE, Harrowell PR (1983) J Am Chem Soc 105:723

    Article  CAS  Google Scholar 

  3. Ward M (2003) Nature 426:615

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  5. Nandi N, Vollhardt D (2003) Chem Rev 103:4033

    Article  CAS  Google Scholar 

  6. Kuzmenko I, Rapaport H, Kjaer K, Als-Nielsen J, Weissbuch I, Lahav M, Leiserowitz L (2001) Chem Rev 101:1659

    Article  CAS  Google Scholar 

  7. Weissbuch I, Kuzmenko I, Berfeld M, Leiserowitz L, Lahav M (2000) J Phys Org Chem 13:426

    Article  CAS  Google Scholar 

  8. Stine KJ (2002) Encyclopedia of Surface and Colloid Science. Marcel Dekker, New York, p 1017

    Google Scholar 

  9. Masel RI (1996) Principles of Adsorption and Reaction on Solid Surfaces. Wiley, New York

    Google Scholar 

  10. Wood EA (1964) J Appl Phys 35:1306

    Article  CAS  Google Scholar 

  11. Park RL, Madden HH Jr (1968) Surf Sci 11:188

    Article  CAS  Google Scholar 

  12. Unertl WN (1996) Physical structure. In: Holloway S, Richardson NV (eds) Surface crystallography, handbook of surface science 1. Elsevier, Amsterdam, chap. 1

    Google Scholar 

  13. Ertl G, Küppers J (1985) Low Energy Electrons and Surface Chemistry, 2nd ed. Wiley-VCH, Weinheim

    Google Scholar 

  14. Paparazzo E (2003) Nat Mater 2:351

    Article  CAS  Google Scholar 

  15. De Feyter S, De Schryver FC (2005) J Chem Phys B 109:4290

    Google Scholar 

  16. Tersoff J, Hamann DR (1985) Phys Rev B 31:805

    Article  CAS  Google Scholar 

  17. Jung TA, Schlittler RR, Gimzewski JK, Tang H, Joachim C (1996) Science 271:181

    CAS  Google Scholar 

  18. Hla SW, Bartels L, Meyer G, Rieder KH (2000) Phys Rev Lett 85:2777

    Article  CAS  Google Scholar 

  19. Atanasoska LL, Buchholz JC, Somorjai GA (1978) Surf Sci 72:189

    Article  CAS  Google Scholar 

  20. Pendry JB (1994) Surf Sci 299/300:375

    Article  Google Scholar 

  21. Barlow S, Raval R (2003) Surf Sci Rep 50:201

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  23. DeFeyter S, De Schryver (2003) Chem Soc Rev 32:139

    Article  CAS  Google Scholar 

  24. Cai Y, Bernasek SL (2005) J Phys Chem B 109:6233

    Article  CAS  Google Scholar 

  25. Fasel R, Wider J, Quitmann C, Ernst KH, Greber T (2004) Angew Chem Int Ed 43:2853

    Article  CAS  Google Scholar 

  26. Barbosa LAMM, Sautet P (2001) J Am Chem Soc 123:6639

    Article  CAS  Google Scholar 

  27. Humblot V, Ortega Lorenzo M, Baddeley CJ, Haq S, Raval R (2004) J Am Chem Soc 126:6460

    Article  CAS  Google Scholar 

  28. Parschau M, Romer S, Ernst KH (2004) J Am Chem Soc 126:15398

    CAS  Google Scholar 

  29. Parschau M, Kampen T, Ernst KH (2005) Chem Phys Lett 407:433

    Article  CAS  Google Scholar 

  30. Lopinski G, Moffat DJ, Wayner DDM, Wolkow RA (1998) Nature 392:909

    Article  CAS  Google Scholar 

  31. Baiker A (2000) J Mol Catal A: Chemical 163:205

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  33. Kruchten F, Knorr K, Volkmann UG, Taub H, Hansen FY, Matthies B, Herwig KW (2005) Langmuir 21:7507

    Article  CAS  Google Scholar 

  34. Charra F, Cousty J (1998) Phys Rev Lett 80:1682

    Article  CAS  Google Scholar 

  35. Qiu X, Wang C, Zeng Q, Xu B, Yin S, Wang H, Xu S, Bai C (2000) J Am Chem Soc 122:5550

    Article  CAS  Google Scholar 

  36. Qiu X, Wang C, Yin S, Zeng Q, Xu B, Bai C (2000) J Phys Chem B 104:3570

    Article  CAS  Google Scholar 

  37. Steinrück HP, Huber W, Pache T, Menzel D (1989) Surf Sci 218:293

    Article  Google Scholar 

  38. Neuber M, Schneider F, Zubrägel C, Neumann M (1995) J Phys Chem 99:9160 and refs therein

    Article  CAS  Google Scholar 

  39. Weissbuch I, Addadi L, Lahav M, Leiserovitz L (1991) Science 253:637

    CAS  Google Scholar 

  40. Bouropoulos N, Weiner S, Addadi L (2001) Chem Eur J 7:1881

    Article  CAS  Google Scholar 

  41. Orme CA, Noy A, Wierzbicki A, McBride MT, Grantham M, Teng HH, Dove PM, DeYoreo JJ (2001) Nature 411:775

    Article  CAS  Google Scholar 

  42. Ahmadi A, Attard GA, Feliu J, Rodes A (1999) Langmuir 15:2420

    Article  CAS  Google Scholar 

  43. Horvath JD, Gellman A (2002) J Am Chem Soc 124:2384

    Article  CAS  Google Scholar 

  44. Fasel R, Parschau M, Ernst KH (2003) Angew Chem Int Ed 42:5178

    Article  CAS  Google Scholar 

  45. Stocker W, Schumacher M, Graff S, Thierry A, Wittmann JC, Lotz B (1998) Macromolecules 31:807

    Article  CAS  Google Scholar 

  46. De Rosa C (2003) Top Stereochem 24:71

    Google Scholar 

  47. De Feyter S, Grim PCM, Rücker M, Vanoppen P, Meiners C, Sieffert M, Valiyaveetitil S, Müllen K, De Schryver FC (1998) Angew Chem Int Ed Engl 37:1223

    Article  Google Scholar 

  48. Miura A, Jonkheijm P, De Feyter S, Schenning APHJ, Meijer EW, Schryver FC (2005) Small 1:131

    Article  CAS  Google Scholar 

  49. Yoo H, Fain SC Jr, Satija S, Passell L (1986) Phys Rev Lett 56:244

    Article  Google Scholar 

  50. Yoo H, Fain SC Jr (1985) Surf Sci 151:361

    Article  Google Scholar 

  51. de Wild M, Berner S, Suzuki H, Yanagi H, Schlettwein D, Ivan S, Baratoff A, Güntherodt H-J, Jung TA (2002) ChemPhysChem 3:881

    Google Scholar 

  52. Böhringer M, Morgenstern K, Schneider WD, Berndt R (1999) Angew Chem Int Ed 38:821

    Article  Google Scholar 

  53. Barth JV, Brune H, Ertl G, Behm RJ (1990) Phys Rev B 42:9307

    Article  CAS  Google Scholar 

  54. Böhringer M, Morgenstern K, Schneider WD, Berndt R, Mauri F, De Vita A, Car R (1999) Phys Rev Lett 83:324

    Article  Google Scholar 

  55. Weckesser J, De Vita A, Barth JV, Cai C, Kern K (2001) Phys Rev Lett 87:096101

    Article  CAS  Google Scholar 

  56. Kim BI, Cai C, Deng X, Perry SS (2003) Surf Sci 538:45

    Article  CAS  Google Scholar 

  57. Chen Q, Frankel DJ, Richardson NV (2002) Langmuir 18:3219

    Article  CAS  Google Scholar 

  58. Kelly REA, Kantorovich LN (2005) Surf Sci 589:139

    Article  CAS  Google Scholar 

  59. Blüm M-C, Ćavar E, Pivetta M, Patthey F, Schneider WD (2005) Angew Chem Int Ed 44:5334

    Article  CAS  Google Scholar 

  60. Toomes RL, Kang JH, Woodruff DP, Polcik M, Kittel M, Hoeft JT (2003) Surf Sci Lett 522:L9

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  67. Rankin RB, Sholl DS (2005) J Phys Chem B 109:16764 and refs therein

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  70. Dmitriev A, Spillmann H, Lin N, Barth JV, Kern K (2003) Angew Chem Int Ed 42:2670

    Article  CAS  Google Scholar 

  71. Ortega Lorenzo M, Haq S, Bertrams T, Murray P, Raval R, Baddeley CJ (1999) J Phys Chem B 103:10661

    Article  CAS  Google Scholar 

  72. Romer S, Behzadi B, Fasel R, Ernst KH (2005) Chem Eur J 11:4149

    Article  CAS  Google Scholar 

  73. Zhang J, Gesquière A, Sieffert M, Klapper M, Müllen K, De Schryver FC, De Feyter S (2005) Nano Lett 5:1395

    Article  CAS  Google Scholar 

  74. Fasel R, Cossy A, Ernst KH, Baumberger F, Greber T, Osterwalder J (2001) J Chem Phys 115:1020

    Article  CAS  Google Scholar 

  75. Kühnle A, Linderoth TR, Hammer B, Besenbacher F (2002) Nature 415:891

    Article  Google Scholar 

  76. Easson LH, Stedman E (1933) Biochem J 27:1257

    CAS  Google Scholar 

  77. Booth TD, Wahnon D, Wainer IW (1997) Chirality 9:96

    Article  CAS  Google Scholar 

  78. Kühnle A, Molina LM, Linderoth TR, Hammer B, Besenbacher F (2004) Phys Rev Lett 93:086101

    Article  CAS  Google Scholar 

  79. Arnett EM, Chao J, Kinzig B, Stewart MV, Thompson O, Verbiar RJ (1982) J Am Chem Soc 104:389

    Article  CAS  Google Scholar 

  80. Lahav M, Leiserowitz L (1999) Angew Chem Int Ed 38:2533

    Article  CAS  Google Scholar 

  81. Pérez-García L, Amabilino DB (2002) Chem Soc Rev 31:342

    Article  CAS  Google Scholar 

  82. De Feyter S, Gesquière A, Wurst K, Amabilino DB, Veciana J, De Schryver FC (2001) Angew Chem Int Ed 40:3217

    Article  Google Scholar 

  83. Böhringer M, Schneider WD, Berndt R (2000) Angew Chem Int Ed 39:795

    Article  Google Scholar 

  84. Cai Y, Bernasek SL (2003) J Am Chem Soc 125:1655

    Article  CAS  Google Scholar 

  85. Wie Y, Kannappan K, Flynn GW, Zimmt MB (2004) J Am Chem Soc 126:5318

    Article  CAS  Google Scholar 

  86. Vidal F, Delvigne E, Stepanow S, Lin N, Barth JV, Kern K (2005) J Am Chem Soc 127:10101

    Article  CAS  Google Scholar 

  87. Cai Y, Bernasek SL (2005) J Phys Chem B 109:4514

    Article  CAS  Google Scholar 

  88. Fasel R, Parschau M, Ernst KH (2006) Nature 439:449

    Article  CAS  Google Scholar 

  89. Chen Q, Lee CW, Frankel DJ, Richardson NV (1999) Phys Chem Comm 9

    Google Scholar 

  90. France CB, Parkinson BA (2003) J Am Chem Soc 125:12712

    Article  CAS  Google Scholar 

  91. France CB, Parkinson BA (2004) Langmuir 20:2713

    Article  CAS  Google Scholar 

  92. Ernst KH, Kuster Y, Fasel R, Müller M, Ellerbeck U (2001) Chirality 13:675

    Article  CAS  Google Scholar 

  93. Ernst KH, Parschau M, Fasel R (2004) J Surf Sci Nanotech 2:136

    Article  CAS  Google Scholar 

  94. Ortega Lorenzo M, Humblot V, Murray P, Baddeley CJ, Haq S, Raval R (2002) J Catal 205:123

    Article  CAS  Google Scholar 

  95. Stepanov S, Lin N, Vidal F, Landa A, Ruben M, Barth JV, Kern K (2005) Nano Lett 5:901

    Article  CAS  Google Scholar 

  96. Schönherr H, Crego-Calama M, Vansco JG, Reinhoudt DN (2004) Adv Mater 16:1416

    Article  CAS  Google Scholar 

  97. Ortega Lorenzo M, Baddeley CJ, Muryn C, Raval R (2000) Nature 404:376

    Article  Google Scholar 

  98. Jones TE, Baddeley CJ (2002) Surf Sci 519:237

    Article  CAS  Google Scholar 

  99. Bonello JM, Williams FJ, Lambert RM (2003) J Am Chem Soc 125:2723

    Article  CAS  Google Scholar 

  100. Behzadi B, Romer S, Fasel R, Ernst KH (2004) J Am Chem Soc 126:9176

    Article  CAS  Google Scholar 

  101. Falconer JL, Madix RJ (1974) Surf Sci 46:473

    Article  CAS  Google Scholar 

  102. Chen Q, Richardson NV (2003) Nat Mater 2:324

    Article  CAS  Google Scholar 

  103. Hermse CGM, van Bavel AP, Jansen APJ, Barbosa LAMM, Sautet P, van Santen RA (2004) J Phys Chem B 108:11035

    Article  CAS  Google Scholar 

  104. Lukas S, Witte G, Wöll C (2002) Phys Rev Lett 88:28301

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  106. Green MM, Garetz BA, Munoz B, Chang H, Hoke S, Cooks RG (1995) J Am Chem Soc 117:4181

    Article  CAS  Google Scholar 

  107. Green MM, Park JW, Sato T, Teramoto A, Lifson S, Selinger RLB, Selinger JV (1999) Angew Chem Int Ed 38:3138

    Article  Google Scholar 

  108. Selinger JV, Selinger RLB (1997) Phys Rev E 55:1728

    Article  CAS  Google Scholar 

  109. Selinger JV, Selinger RLB (1996) Phys Rev Lett 76:58

    Article  CAS  Google Scholar 

  110. Humblot V, Haq S, Muryn C, Hofer WA, Raval R (2002) J Am Chem Soc 124:503

    Article  CAS  Google Scholar 

  111. Mamdouh W, Uji-i H, Gesquière A, De Feyter S, Amabilino DB, Abdel-Mottaleb MMS, Veciana J, De Schryver FC (2004) Langmuir 20:9628

    Article  CAS  Google Scholar 

  112. Mougous JD, Brackley AJ, Foland K, Baker RT, Patrick DL (2000) Phys Rev Lett 84:2742

    Article  CAS  Google Scholar 

  113. Berg AM, Patrick DL (2005) Angew Chem Int Ed 44:1821

    Article  CAS  Google Scholar 

  114. Smith DPE (1991) J Vac Sci Technol B 9:1119

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Empa, Swiss Federal Laboratories for Materials Testing and Research, Überlandstrasse 129, 8600, Dübendorf, Switzerland

    Karl-Heinz Ernst

Authors
  1. Karl-Heinz Ernst
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Karl-Heinz Ernst .

Editor information

Mercedes Crego-Calama David N. Reinhoudt

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Ernst, KH. Supramolecular Surface Chirality. In: Crego-Calama, M., Reinhoudt, D.N. (eds) Supramolecular Chirality. Topics in Current Chemistry, vol 265. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_036

Download citation

Publish with us

Policies and ethics

Search

Navigation