Hierarchical self-assembly on silicon

Journal of the American Chemical Society

Volumn 132, Issue 13, 2010, Pages 4781-4789

  Tancini, Francesca ^a   Genovese, Damiano ^b   Montalti, Marco ^b   Cristofolini, Luigi ^a   Nasi, Lucia ^c   Prodi, Luca ^b   Dalcanale, Enrico ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c IMEM CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ASSEMBLY MODES; BINDING MOTIF; CAVITANDS; COMPLEXING PROPERTIES; EXTERNAL STIMULUS; FULLY COMPATIBLE; H-BONDING; HIERARCHICAL SELF-ASSEMBLY; HOST GUEST INTERACTIONS; HOST-GUESTS; MODULAR COMPONENTS; MOLECULAR LEVEL CONTROL; ORTHOGONALITY; SINGLE MOLECULE; SUPRAMOLECULAR STRUCTURE; SURFACE ANALYSIS TECHNIQUES;

ATOMIC FORCE MICROSCOPY; CRYSTAL ATOMIC STRUCTURE; DRUG INTERACTIONS; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY; SEMICONDUCTING SILICON COMPOUNDS; SURFACE ANALYSIS;

SILICON WAFERS;

HETERODIMER; METHYLAMMONIUM; PICOLINE DERIVATIVE; SILICON;

ACCURACY; ARTICLE; ATOMIC FORCE MICROSCOPY; DIMERIZATION; ELLIPSOMETRY; FLUORESCENCE; HOST; HYDROGEN BOND; MOLECULE; PREDICTION; RELIABILITY; SOLID STATE; SURFACE PROPERTY;

DIMERIZATION; HYDROGEN BONDING; MOLECULAR CONFORMATION; ORGANOPHOSPHORUS COMPOUNDS; ORGANOSILICON COMPOUNDS; PARTICLE SIZE; SILICON; STEREOISOMERISM; SURFACE PROPERTIES;

EID: 77950843236     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9099938     Document Type: Article

References (47)

1. Descalzo, A. B., Martnez-Màòez, R., Sancenòn, F., Hoffmann, K., and Rurack, K. Angew. Chem., Int. Ed. 2006, 45, 5924 - 5948
2. Lehn, J. M. Chem. - Eur. J. 1999, 5, 2455 - 2463
3. H-bonding: De Feyter, S. and De Schryver, F. C. Chem. Soc. Rev. 2003, 32, 139 150
4. Theobald, J. A., Oxtoby, N. S., Phillips, M. A., Champness, N. R., and Beton, P. H. Nature 2003, 424, 1029 1031
5. Ruben, M., Payer, D., Landa, A., Comisso, A., Gattinoni, C., Lin, N., Collin, J. P., Sauvage, J.-P., De Vita, A., and Kern, K. J. Am. Chem. Soc. 2006, 128, 15644 15651
6. Llanes-Pallas, A., Matena, M., Jung, T., Prato, M., Stöhr, M., and Bonifazi, D. Angew. Chem., Int. Ed. 2008, 47, 7726 7730
7. Madueno, R., Räisänen, M. T., Silien, C., and Buck, M. Nature 2008, 454, 618 - 621
8. Host-guest: Ludden, M. J. W., Reinhoudt, D. N., and Huskens, J. Chem. Soc. Rev. 2006, 35, 1122 - 1134
9. Ludden, M. J. W., Mulder, A., Tampè, R., Reinhoudt, D. N., and Huskens, J. Angew. Chem., Int. Ed. 2007, 46, 4104 - 4107
10. Metal-ligand coordination: Weissbuch, I., Baxter, P. N. W., Cohen, S., Cohen, H., Kjaer, K., Howes, P. B., Als-Nielsen, J., Hanan, G. S., Schubert, U. S., Lehn, J.-M., Leiserowitz, L., and Lahav, M. J. Am. Chem. Soc. 1998, 120, 4850 - 4860
11. Hatzor, A., Moav, T., Cohen, H., Matlis, S., Libman, J., Vaskevich, A., Shanzer, A., and Rubinstein, I. J. Am. Chem. Soc. 1998, 120, 13469 - 13477
12. Levi, S., Guatteri, P., van Veggel, F. C. J. M., Vancso, G. J., Dalcanale, E., and Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 1892 - 1896
13. Busi, M., Laurenti, M., Condorelli, G. G., Motta, A., Favazza, M., Fragalà, I. L., Montalti, M., Prodi, L., and Dalcanale, E. Chem. - Eur. J. 2007, 13, 6891 - 6898
14. Li, S.-S., Northrop, B. H., Yuan, Q.-H., Wan, L.-J., and Stang, P. J. Acc. Chem. Res. 2009, 42, 249 - 259
15. --Stacking: Bhosale, R., Perez-Velasco, A., Ravikumar, V., Kishore, R. S. K., Kel, O., Gomez-Casado, A., Jonkheijm, P., Huskens, J., Maroni, P., Borkovec, M., Sawada, T., Vauthey, E., Sakai, N., and Matile, S. Angew. Chem., Int. Ed. 2009, 48, 6461 - 6464
16. Kishore, R. S. K., Kel, O., Banerji, N., Emery, D., Bollot, G., Mareda, J., Gomez-Casado, A., Jonkheijm, P., Huskens, J., Maroni, P., Borkovec, M., Vauthey, E., Sakai, N., and Matile, S. J. Am. Chem. Soc. 2009, 131, 11106 - 11116
17. Langner, A., Tait, S. L., Lin, N., Chandrasekar, R., Ruben, M., and Kern, K. Angew. Chem., Int. Ed. 2008, 47, 8835 - 8838
18. For alternative combinations of orthogonal interaction modes on surfaces, see: Corbellino, F., Mulder, A., Sartori, A., Ludden, M. J. W., Casnati, A., Ungaro, R., Huskens, J., Crego-Calamata, M., and Reinhoudt, D. N. J. Am. Chem. Soc. 2004, 126, 17050 17058
19. Ludden, M. J. W., Huskens, J., and Reinhoudt, D. N. Small 2006, 1192 - 1202
20. For the combination of weak interactions in supramolecular polymers see: Hofmeier, H. and Schubert, U. S. Chem. Commun. 2005, 2423 - 2432
21. Beijer, F. H., Sijbesma, R. P., Kooijman, H., Spek, A. L., and Meijer, E. W. J. Am. Chem. Soc. 1998, 120, 6761 - 6769
22. Corbin, P S. and Zimmermann, S. C. J. Am. Chem. Soc. 1998, 120, 9710 - 9711
23. Wang, X.-Z., Li, X.-Q., Shao, X.-B., Zhao, X., Deng, P., Jiang, X.-K., Li, Z.-T., and Chen, Y.-Q. Chem. - Eur. J. 2003, 9, 2904 - 2913
24. Park, T., Todd, E. M., Nakashima, S., and Zimmermann, S. C. J. Am. Chem. Soc. 2005, 127, 18133 - 18142
25. de Greef, T. F. A., Ligthart, G. B. W. L., Lutz, M., Spek, A. L., Meijer, E. W., and Sijbesma, R P. J. Am. Chem. Soc. 2008, 130, 5479 - 5486
26. Pinalli, R., Suman, M., and Dalcanale, E. Eur. J. Org. Chem. 2004, 451 - 462
27. Pirondini, L. and Dalcanale, E. Chem. Soc. Rev. 2007, 36, 695 - 706
28. Biavardi, E., Battistini, G., Montalti, M., Yebeutchou, R. M., Prodi, L., and Dalcanale, E. Chem. Commun. 2008, 1638 - 1640
29. Yebeutchou, R. M., Tancini, F., Demitri, N., Geremia, S., Mendichi, R., and Dalcanale, E. Angew. Chem., Int. Ed. 2008, 47, 4504 - 4507
30. Biavardi, E., Favazza, M., Motta, A., Fragala, I. L., Massera, C., Prodi, L., Montalti, M., Melegari, M., Condorelli, G., and Dalcanale, E. J. Am. Chem. Soc. 2009, 131, 7447 - 7455
31. Gadenne, B., Semeraro, M., Yebeutchou, R. M., Tancini, F., Pirondini, L., Dalcanale, E., and Credi, A. Chem. - Eur. J. 2008, 14, 8964 - 8971
32. Xu, W., Rourke, J. P., and Puddephatt, R. J. R. Chem. Commun. 1993, 145 - 147
33. Keizer, H. M., Van Kessel, R., Sijbesma, R. P., and Meijer, E. W. Polymer 2003, 44, 5505 - 5511
34. Alvarez-Rua, C., Garcia-Granda, S., Goswami, S., Mukherjee, R., Dey, S., Claramunt, R. M., Maria, M. D. S., Rozas, I., Jagerivic, N., Alkorta, I., and Elguero, J. New J. Chem. 2004, 28, 700 - 707
35. Corbin, P. S., Zimmerman, S. C., Thiessen, P. A., Hawriluk, N. A., and Murray, T. J. J. Am. Chem. Soc. 2001, 123, 10475 - 10488
36. Lightart, G. B. W. L., Ohkawa, H., Sijbesma, R. P., and Meijer, E. W. J. Org. Chem. 2006, 71, 375 - 378
37. Bibal, B., Tinant, B., Declercq, J.-P., and Dutasta, J.-P. Supramol. Chem. 2003, 15, 25 - 32
38. Sontjens, S. H. M., Sijbesma, R. P., Van Genderen, M. H. P., and Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 7487 - 7493
39. Zhao, X., Wang, X.-Z., Jiang, X.-K., Chen, Y.-Q., Li, Z.-T., and Chen, G.-J. J. Am. Chem. Soc. 2003, 125, 15128 - 15139
40. Li, X.-Q., Feng, D.-J., Jiang, X.-K., and Li, Z.-T. Tetrahedron 2004, 60, 8275 - 8284
41. Dutasta, J.-P. Phosphorus, Sulfur Silicon 2002, 177, 1485 - 1488
42. Condorelli, G. G., Motta, A., Favazza, M., Fragalà, I. L., Busi, M., Menozzi, E., Dalcanale, E., and Cristofolini, L. Langmuir 2006, 22, 11126 - 11133
43. Chen, T., Ferris, R., Zhang, J., Ducker, R., and Zauscher, S. Prog. Polym. Sci. 2010, 35, 94 - 112
44. Azzam, R. M. A. and Bashara, N. M. Ellipsometry and Polarized Light; North Holland: Amsterdam. 1977.
45. Harke, M., Teppner, R., Schulz, O., and Motschmann, H. Rev. Sci. Instrum. 1997, 68, 3130 - 3134
46. Tompkins, H. A Users Guide to Ellipsometry; Academic Press: Boston, 1993.
47. This value is higher than expected for the cavitand layer (2.0 nm). The presence of adventitious carbon has been shown to increase the organic layer thickness in silicon wafers. See: Subramanian, V., Bhattacharya, P. K., and Memon, A. A. Int. J. Electron. 1995, 78, 519 - 525