Building supramolecular nanostructures at surfaces by hydrogen bonding

Angewandte Chemie - International Edition

Volumn 39, Issue 7, 2000, Pages 1230-1234

  Barth, Johannes V ^a   Weckesser, Jens ^a   Cai, Chengzhi ^b   Günter, Peter ^b   Bürgi, Lukas ^a   Jeandupeux, Olivier ^a   Kern, Klaus ^a,c  

^a EPFL   (Switzerland)

^b ETH ZURICH   (Switzerland)

^c MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

Hydrogen bonds; Nanostructures; Scanning tunneling microscopy; Supramolecular chemistry; Surface chemistry

Indexed keywords

BENZOIC ACID DERIVATIVE;

ADSORPTION; ANISOTROPY; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL; GEOMETRY; HYDROGEN BOND; MOLECULAR INTERACTION; NANOPARTICLE; PROTEIN STRUCTURE; SCANNING TUNNELING MICROSCOPY;

EID: 0034599668     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000403)39:7<1230::AID-ANIE1230>3.0.CO;2-I     Document Type: Article

References (36)

1. G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 154, 1312-1319.
2. J. S. Lindsey, New J. Chem. 1991, 15, 153-180.
3. D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286;
4. Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
5. J. R. Fredericks, A. D. Hamilton in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, J.-M. Lehn), Pergamon, New York, 1996, pp. 565-594.
6. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997.
7. Comprehensive Supramolecular Chemistry (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, J.-M. Lehn), Pergamon, New York, 1996.
8. J. Veciana, J. Cirujeda, C. Rovira, E. Molins, J. J. Novoa, J. Phys. I 1996, 6, 1967.
9. K. Eichhorst-Gerner, A. Stabel, G. Moessner, D. Declerq, S. Valiyaveettil, V. Enkelmann, K. Müllen, P. Rabe, Angew. Chem. 1996, 108, 1599-1602;
10. Angew. Chem. Int. Ed. Engl. 1996, 35, 1492-1495.
11. R. P. Sijbesma, F. H. Beijer, L. Brunsveld, B. J. B. Folmer, J. H. K. K. Hirschberg, R. F. M. Lange, J. K. L. Lowe, E. W. Meijer, Science 1997, 278, 1601-1603.
12. K. A. Jolliffe, P. Timmermann, D. N. Reinhoudt, Angew. Chem. 1999, 111, 983-986;
13. Angew. Chem. Int. Ed. 1999, 38, 933-937.
14. C. Cai, M. Bösch, B. Müller, Y. Tao, A. Kündig, C. Bosshard, Z. Gan, I. Biaggio, I. Liakatas, M. Jäger, H. Schwer, P. Günter, Adv. Mater. 1999, 11, 745-749.
15. C. Cai, B. Müller, J. Weckesser, J. V. Barth, Y. Tao, M. M. Bösch, A. Kündig, C. Bosshard, I. Biaggio, P. Günter, Adv. Mater. 1999, 11, 750-754.
16. T. Kawai, H. Tanaka, T. Nakagawa, Surf. Sci. 1997, 386, 124-136.
17. J. K. Gimzewski, C. Joachim, Science 1999, 283, 1683-1688.
18. M. Böhringer, K. Morgenstern, W.-D. Schneider, R. Berndt, F. Mauri, A. D. Vita, R. Car, Phys. Rev. Lett. 1999, 83, 324-327.
19. P. Samorí, V. Francke, K. Müllen, J. P. Rabe, Chem.. Eur. J. 1999, 5, 2312-2317.
20. E. Umbach, M. Sokolowski, R. Fink, Appl. Phys. A 1996, 63, 565-576.
21. S. R. Forrest, Chem. Rev. 1997, 97, 1793-1896.
22. J. Weckesser, J. V. Barth, K. Kern, J. Chem. Phys. 1999, 110, 5351-5354.
23. J. Weckesser, J. V. Barth, C. Cai, B. Müller, K. Kern, Surf. Sci. 1999, 437, 268-173.
24. C. C. Perry, S. Haq, B. G. Frederick, N. V. Richardson, Surf. Sci. 1998, 409, 512-520.
25. The dark lines between the PVBA chains are an electron standing wave pattern.
26. A. Hirstein, PhD thesis, EPF Lausanne, 1998.
27. O. Jeandupeux, L. Bürgi, A. Hirstein, H. Brune, K. Kern, Phys. Rev. B 1999, 59, 15926-15934.
28. The geometry of the molecule was simulated with AM1 (implemented in the MOPAC program packet Cerius 2, BIOSYM/Molecular Simulations).
29. G. A. Jeffrey in Landolt-Börnstein Series, Vol. VII:1b (Ed.: W. Saenger), Springer, Berlin, 1989, pp. 277-348.
30. F. Takusagawa, A. Shimada, Acta Crystallogr. Sect. B 1976, 32, 1925-1927.
31. G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441.
32. This is believed to be the reason for the closer proximity of C-H ⋯ O with the β-pyridyl H-atom instead of the α-pyridyl H-atom, which could be expected for an unrestricted arrangement on an ideally flat surface. Calculations are currently being performed to elucidate the nature of the molecular interactions in more detail.
33. J. V. Barth, H. Brune, R. J. Behm, G. Ertl, Phys. Rev. B 1990, 42, 9307-9318.
34. K. Kern, H. Niehus, A. Schatz, P. Zeppenfeld, J. George, G. Comsa, Phys. Rev. Lett. 1991, 67, 855-858.
35. D. Vanderbilt, Surf. Sci. 1992, 268, L300-L304.
36. A. de Vita, J. Weckesser, J. V. Barth, K. Kern, unpublished results.