Protecting-group-controlled surface chemistry-organization and heat-induced coupling of 4,4′-di(tert-butoxycarbonylamino)biphenyl on metal surfaces

Angewandte Chemie - International Edition

Volumn 48, Issue 17, 2009, Pages 3179-3183

  Boz, Serpil ^a   Stöhr, Meike ^a   Soydaner, Umut ^a   Mayor, Marcel ^a,b  

^a UNIVERSITY OF BASEL   (Switzerland)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

METAL SURFACES; MOLECULAR BUILDING BLOCKS; PROTECTING GROUP; STM IMAGES; SUPRAMOLECULAR SELF-ASSEMBLIES; THERMAL ACTIVATION;

SURFACE CHEMISTRY;

EID: 70349900191     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804845     Document Type: Article

References (29)

1. J.-M. Lehn, Supramolecular chemistry: concepts and perspectives, Wiley-VCH, Weinheim, 1995.
2. S. De Feyter, F. C. De Schryver, Chem. Soc. Rev. 2003, 32, 139.
3. J. V. Barth, Annu. Rev. Phys. Chem. 2007, 58, 375.
4. N. Lin, A. Dmitriev, J. Weckesser, J. V. Barth, K. Kern, Angew. Chem. 2002, 114, 4973; Angew. Chem. Int. Ed. 2002, 41, 4779.
5. 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.
6. J. A. Theobald, N. S. Oxtoby, M. A. Phillips, N. R. Champness, P. H. Beton, Nature 2003, 424, 1029.
7. M. De Wild, S. Berner, H. Suzuki, H. Yanagi, D. Schlettwein, S. Ivan, A. Baratoff, H.-J. Güntherodt, T. A. Jung, ChemPhysChem 2002, 3, 881.
8. H. Ozaki, T. Funaki, Y. Mazaki, S. Masuda, Y. Harada, J. Am. Chem. Soc. 1995,117, 5596.
9. S. W. Hla, L. Bartels, G. Meyer, K. H. Rieder, Phys. Rev. Lett. 2000, 85, 2777.
10. Y. Okawa, M. Aono, Nature 2001, 409, 683.
11. A. Miura, S. De Feyter, M. M. S. Abdel-Mottaleb, A. Gesquiere, P. C. M. Grim, G. Moessner, M. Sieffert, M. Klapper, K. Müllen, F. C. De Schryver, Langmuir 2003, 19, 6474.
12. J. Barner, F. Mallwitz, L. Shu, A. D. Schlüter, J. P. Rabe, Angew. Chem. 2003, 115, 1976; Angew. Chem. Int. Ed. 2003, 42, 1932.
13. L. Grill, M. Dyer, L. Lafferentz, M. Persson, M. V. Peters, S. Hecht, Nat. Nanotechnol. 2007, 2, 687.
14. (a)S. Weigelt, C. Busse, C. Bombis, M. M. Knudsen, K. V. Gothelf, T. Strunskus, C. Wöll, M. Dahlbom, B. Hammer, E. Laegsgaard, F. Besenbacher, T. R. Linderoth, Angew. Chem. 2007, 119, 9387; Angew. Chem. Int. Ed. 2007, 46, 9227;
15. b) S. Weigelt, C. Busse, C. Bombis, M. M. Knudsen, K. V. Gothelf, E. Laegsgaard, F. Besenbacher, T. R. Linderoth, Angew. Chem. 2008, 120, 4478; Angew. Chem. Int. Ed. 2008, 47, 4406.
16. M. Matena, T. Riehm, M. Stöhr, T. A. Jung, L. H. Gade, Angew. Chem. 2008, 120, 2448; Angew. Chem. Int. Ed. 2008, 47, 2414.
17. M. In't Veld, P. Iavicoli, S. Haq, D. B. Amabilino, R. Raval, Chem. Commun. 2008, 1536.
18. (a)N. A. A. Zwaneveld, R. Pawlak, M. Abel, D. Catalin, D. Gigmes, D. Bertin, L. Porte, J. Am. Chem. Soc. 2008, 130, 6678;
19. b) M. Treier, N. V. Richardson, R. Fasel, J. Am. Chem. Soc. 2008, 130, 14054.
20. P. G. M. Wuts, T. W. Greene in Greene's Protective Groups in Organic Synthesis, 4th ed., Wiley, Hoboken, NJ, 2007.
21. P. J. KocieŃski in Protecting Groups, 3rd ed., Thieme, Stuttgart, 2005.
22. F. Moresco, G. Meyer, K.-H. Rieder, J. Ping, H. Tang, C. Joachim, Surf. Sci. 2002, 499, 94.
23. T. A. Jung, R. R. Schlittler, G. K. Gimzewski, Nature 1997, 386, 696.
24. J. Henzl, M. Mehlhorn, H. Gawronski, K. H. Rieder, K. Morgenstern, Angew. Chem. 2006, 118, 617; Angew. Chem. Int. Ed. 2006, 45, 603.
25. M. J. Comstock, N. Levy, A. Kirakosian, J. Cho, F. Lauterwasser, J. H. Harvey, D. A. Strubbe, J. M. J. Frechet, D. Trauner, S. G. Louie, M. F. Crommie, Phys. Rev. Lett. 2007, 99, 038301.
26. S. Weigelt, C. Busse, L. Petersen, E. Rauls, B. Hammer, K. V. Gothelf, F. Besenbacher, T. R. Linderoth, Nat. Mater. 2006, 5, 112.
27. S. Berner, M. Brunner, L. Ramoino, H. Suzuki, H.-J. Günther- odt, T. A. Jung, Chem. Phys. Lett. 2001, 348, 175.
28. See the Supporting Information.
29. lf-assembles in a herringbone structure on Ag(lll) and the formation of polymers has been observed upon annealing at 200 °C. These experiments are described in detail in the Supporting Information.