Asymmetry induction by cooperative intermolecular hydrogen bonds in surface-anchored layers of achiral molecules

ChemPhysChem

Volumn 7, Issue 10, 2006, Pages 2197-2204

  Dmitriev, Alexandre ^a,f   Spillmann, Hannes ^a   Stepanow, Sebastian ^a   Strunskus, Thomas ^b   Wöll, Christof ^b   Seitsonen, Ari P ^c   Lingenfelder, Magali ^a   Lin, Nian ^a   Barth, Johannes V ^d,e   Kern, Klaus ^a,e  

^a MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

^b RUHR UNIVERSITY BOCHUM   (Germany)

^c CNRS   (France)

^d UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^e EPFL   (Switzerland)

^f CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

Chirality; Density functional calculations; Hydrogen bonds; Photoelectron spectroscopy; Scanning probe microscopy

Indexed keywords

ABSORPTION SPECTROSCOPY; CARBOXYLATION; CHIRALITY; COMPUTATION THEORY; COMPUTATIONAL GEOMETRY; DENSITY FUNCTIONAL THEORY; MOLECULES; MORPHOLOGY; PHOTOELECTRON SPECTROSCOPY; PHOTOELECTRONS; PHOTONS; SCANNING PROBE MICROSCOPY; SCANNING TUNNELING MICROSCOPY; STEREOCHEMISTRY; X RAY ABSORPTION; X RAY PHOTOELECTRON SPECTROSCOPY;

CARBOXYLATE GROUPS; CONFORMATIONAL RESTRICTIONS; ELEVATED TEMPERATURE; INTERMOLECULAR COUPLING; INTERMOLECULAR HYDROGEN BONDS; MOLECULAR ADSORPTION; NEAR EDGE X RAY ABSORPTION FINE STRUCTURE; SUPRAMOLECULAR CHIRALITY;

HYDROGEN BONDS;

EID: 33750277796     PISSN: 14394235     EISSN: 14397641     Source Type: Journal    
DOI: 10.1002/cphc.200600110     Document Type: Article

References (78)

1. A. Ahmadi, G. Attard, Langmuir 1999, 15, 2420.
2. J. D. Horvath, A. J. Gellman, J. Am. Chem. Soc. 2002, 124, 2384.
3. D. S. Sholl, A. Asthagiri, T. D. Power, J. Phys. Chem. B 2001, 105, 4771.
4. R. Fasel, M. Parschau, K.-H. Ernst, Angew. Chem. 2003, 115, 5336;
5. Angew. Chem. Int. Ed. 2003, 42, 5178.
6. V. Humblot, S. Haq, C. Muryn, W. A. Hofer, R. Raval, J. Am. Chem. Soc. 2002, 124, 503.
7. A. Kühnle, T. R. Linderoth, B. Hammer, F. Besenbacher, Nature 2002, 415, 891.
8. G. P. Lopinski, D. D. Wayner, R. A. Wolkow, Nature 2000, 406, 48.
9. M. O. Lorenzo, C. J. Baddeley, C. Muryn, R. Raval, Nature 2000, 404, 376.
10. P. Nassoy, M. Goldmann, O. Bouloussa, F. Rondelez, Phys. Rev. Lett. 1995, 75, 457.
11. D. Stacchiola, L. Burkholder, W. T. Tysoe, J. Am. Chem. Soc. 2002, 124, 8984.
12. R. Fasel, J. Wider, C. Quitmann, K.-H. Ernst, T. Greber, Angew. Chem. 2004, 116, 2913;
13. Angew. Chem. Int. Ed. 2004, 43, 2853.
14. Q. Chen, N. V. Richardson, Nat. Mater. 2003, 2, 324.
15. J. V. Barth, J. Weckesser, G. Trimarchi, M. Vladimirova, A. D. Vita, C. Cai, H. Brune, P. Günter, K. Kern, J. Am. Chem. Soc. 2002, 124, 7991.
16. S. D. Feyter, P. C. M. Grim, M. Rücker, P. Vanoppen, C. Meiners, M. Sieffert, S. Valiyaveettil, K. Müllen, F. C. D. Schryver, Angew. Chem. 1998, 110, 1281;
17. Angew. Chem. Int. Ed. 1998, 37, 1223.
18. S. d. Feyter, A. Gesquiere, K. Wurst, D. B. Amabilino, J. Veciana, F. C. d. Schryver, Angew. Chem. 2001, 113, 3317;
19. Angew. Chem. Int. Ed. 2001, 40, 3217.
20. C. B. France, B. A. Parkinson, J. Am. Chem. Soc. 2003, 125, 12 712.
21. R. Viswanathan, J. A. Zasadzinski, D. K. Schwartz, Nature 1994, 368, 440.
22. J. Weckesser, A. D. Vita, J. V. Barth, C. Cai, K. Kern, Phys. Rev. Lett. 2001, 87, 096101.
23. D. G. Yablon, D. Wintgens, G. W. Flynn, J. Phys. Chem. B 2002, 106, 5470.
24. M. Schunack, E. Laegsgaard, I. Stensgaard, I. Johannsen, F. Besenbacher, Angew. Chem. 2001, 113, 2693;
25. Angew. Chem. Int. Ed. 2001, 40, 2623.
26. J. I. Pascual, J. V. Barth, G. Ceballos, G. Trimarchi, A. D. Vita, K. Kern, H.-P. Rust, J. Chem. Phys. 2003, 120, 11 367.
27. M. Parschau, S. Romer, K.-H. Ernst, J. Am. Chem. Soc. 2004, 126, 15 398.
28. J. A. Switzer, H. M. Kothari, P. Poizot, S. Nakanishi, E. W. Bohannan, Nature 2003, 425, 490.
29. L. Pérez-Garcìa, D. B. Amabilino, Chem. Soc., Rev. 2002, 31, 342.
30. V. Humblot, S. M. Barlow, R. Raval, Prog Surf. Sci. 2004, 76, 1.
31. S. Stepanow, N. Lin, F. Vidal, A. Landa, M. Ruben, J. V. Barth, K. Kern, Nano Lett. 2005, 5, 901.
32. K. Biradha, D. Dennis, V. MacKinnon, C. V. K. Sharma, M. J. Zaworotko, J. Am. Chem. Soc. 1998, 120, 11 894.
33. S. Clair, S. Pons, A. P. Seitsonen, H. Brune, K. Kern, J. V. Barth, J. Phys. Chem. B 2004, 108, 14 585.
34. M. Lackinger, S. Griessl, T. Markert, F. Jamitzky, W. M. Heckl, J. Phys. Chem. B 2004, 108, 13 652.
35. M. Lingenfelder, H. Spillmann, A. Dmitriev, S. Stepanow, N. Lin, J. V. Barth, K. Kern, Chem. Eur. J. 2004, 10, 1913.
36. S. Stepanow, T. Strunskus, M. Lingenfelder, A. Dmitriev, H. Spillmann, N. Lin, J. V. Barth, C. Wöll, K. Kern, J. Phys. Chem. B 2004, 108, 19 392.
37. P. Messina, A. Dmitriev, N. Lin, H. Spillmann, M. Abel, J. V. Barth, K. Kern, J. Am. Chem. Soc. 2002, 124, 14 000.
38. H. Spillmann, A. Dmitriev, N. Lin, P. Messina, J. V. Barth, K. Kern, J. Am. Chem. Soc. 2003, 125, 10 725.
39. A. Dmitriev, H. Spillmann, N. Lin, J. V. Barth, K. Kern, Angew. Chem. Int. Ed. 2003, 115, 2774;
40. Angew. Chem. Int. Ed. 2003, 42, 2670.
41. A. Dmitriev, H. Spillmann, M. Lingenfelder, N. Lin, J. V. Barth, K. Kern, Langmuir 2004, 20, 4799.
42. S. Stepanow, M. Lingenfelder, A. Dmitriev, H. Spillmann, E. Delvigne, N. Lin, X. Deng, C. Cai, J. V. Barth, K. Kern, Nat. Mater. 2004, 3, 229.
43. D. S. Martin, R. J. Cole, S. Haq, Phys. Rev. B 2002, 66, 155 427.
44. A. Dmitriev, N. Lin, J. Weckesser, J. V. Barth, K. Kern, J. Phys. Chem. B 2002, 106, 6907.
45. L. H. Dubois, B. R. Zegarski, R. G. Nuzzo, Langmuir 1986, 2, 412.
46. C. A. Fustin, R. Gouttebaron, C. D. Nadai, R. Caudano, F. Zerbetto, D. A. Leigh, P. Rudolf, Surf. Sci. 2001, 474, 37.
47. S. W. Han, S. W. Joo, T. H. Ha, Y. Kim, K. Kim, J. Phys. Chem. B 2000, 104, 11 987.
48. A. D. Vogt, T. Han, J. T. P. Beebe, Langmuir 1997, 13, 3397.
49. M. Wühn, J. Weckesser, C Wöll, Langmuir 2001, 17, 7605.
50. J. M. Rynkowski, S. Affrossman, J. M. R. MacAllister, R. A. Pethrick, Surf. Sci. 1987, 182, 1.
51. F. Takusagawa, K. Hirotsu, A. Shimada, Bull. Chem. Soc., Jap. 1973, 46, 2960.
52. G. Iucci, V. Carravetta, P. Altamura, M. V. Russo, G. Paolucci, A. Goldoni, Chem. Phys. 2004, 302, 43.
53. T. Bitzer, N. V. Richardson, S. Reiss, M. Wühn, C. Wöll, Surf. Sci. 2000, 458, 173.
54. B. Immaraporn, P. Ye, A. J. Gellman, J. Phys. Chem. B 2004, 108, 3504.
55. B. Parker, B. Immaraporn, A. J. Gellman, Langmuir 2001, 17, 6638.
56. K. Weiss, S. Gebert, M. Wühn, H. Wadepohl, C. Wöll, J. Vac. Sci. Technol. 1998, 16, 1017.
57. S. Haq, F. M. Leibsle, Surf. Sci. 1996, 355, L345.
58. F. Rosei, M. Schunack, P. Jiang, A. Gourdon, E. Laegsgaard, I. Stensgaard, C. Joachim, F. Besenbacher, Science 2002, 296, 328.
59. X. Zhao, J. Am. Chem. Soc. 2000, 122, 12 584.
60. F. S. Tautz, M. Eremtchenko, J. A. Schaefer, M. Sokolowski, V. Shklover, K. Glöckler, E. Umbach, Surf. Sci. 2002, 502-503, 176.
61. X. Zhao, Z. Gai, R. G. Zhao, W. S. Yang, T. Sakurai, Surf. Sci. 1999, 424, L347.
62. Q. Chen, N. V. Richardson, Prog Surf. Sci. 2003, 73, 59.
63. P. Sautet, Chem. Rev. 1997, 97, 1097.
64. A. P. Seitsonen, Y. J. Zhu, K. Beduerftig, H. Over, J. Am. Chem. Soc. 2001, 123, 7347.
65. R. C. Mehrotra, R. Bohra, Metal Carboxylates, Academic Press, London, 1983.
66. B. G. Frederick, Q. Chen, F. M. Leibsle, M. B. Lee, K. J. Kitching, N. V. Richardson, Surf. Sci. 1997, 394, 1.
67. T. Steiner, Angew. Chem. 2002, 114, 50;
68. Angew. Chem. Int. Ed. 2002, 41, 48.
69. G. Desiraju, Acc. Chem. Res. 1996, 29, 441.
70. V. Humblot, M. O. Lorenzo, C. J. Baddeley, S. Haq, R. Raval, J. Am. Chem. Soc. 2004, 126, 6460.
71. A. Mulligan, I. Lane, G. B. D. Rousseau, S. M. Johnston, D. Lennon, M. Kadodwala, Angew. Chem. 2005, 117, 1864;
72. Angew. Chem. Int. Ed. 2005, 44, 1830.
73. J. Stöhr, NEXAFS Spectroscopy, Springer-Verlag, Berlin, Heidelberg, 1992.
74. J. P. Perdew, J. A. Chevary, S. H. Vosko, K. A. Jackson, M. R. Pederson, D. J. Singh, C. Fiolhais, Phys. Rev. B 1992, 46, 6671.
75. The calculations were performed with the program VASP: G. Kresse, J. Furthmüller, Comput. Mater. Sci. 1996, 6, 15;
76. G. Kresse, J. Furthmüller, Phys. Rev. B 1996, 54, 11 169.
77. D. Vanderbilt, Phys. Rev. B 1990, 41, 7892.
78. H. J. Monkhorst, J. D. Pack, Phys. Rev. B 1976, 13, 5188.