Stepwise formation and characterization of covalently linked multiporphyrin-ilmide architectures on SI(100)

Journal of the American Chemical Society

Volumn 128, Issue 21, 2006, Pages 6965-6974

  Jiao, Jieying ^a   Anariba, Franklin ^a   Tiznado, Hugo ^a   Schmidt, Izabela ^b   Lindsey, Jonathan S ^b   Zaera, Francisco ^a   Bocian, David F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ATOMIC FORCE MICROSCOPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; OLIGOMERS; SYNTHESIS (CHEMICAL); THIN FILMS;

MOLECULAR ARCHITECTURE; MOLECULAR ELECTRONICS; MULTIPORPHYRIN-ILMIDE ARCHITECTURES; SEMICONDUCTOR SYSTEMS;

PORPHYRINS;

3,3',4,4' BIPHENYLTETRACARBOXYLIC DIANHYDRIDE; ACID ANHYDRIDE; ALLYL COMPOUND; DIAMINE; IMIDE; NANOPARTICLE; OLIGOMER; PORPHYRIN DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; COVALENT BOND; DENSITY; DEVICE; ELECTROCHEMICAL ANALYSIS; ELECTRONICS; ELLIPSOMETRY; EVALUATION; FILM; INFORMATION STORAGE; INFRARED SPECTROSCOPY; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; SEMICONDUCTOR; STRUCTURE ANALYSIS; SYNTHESIS; THICKNESS; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 33744824917     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060906q     Document Type: Article

References (47)

1. (a) Roth, K. M.; Dontha, N.; Dabke, R. B.; Gryko, D. T.; Clausen, C.; Lindsey, J. S.; Bocian, D. F.; Kuhr, W. G. J. Vac. Sci. Technol., B. 2000, 18, 2359-2364.
2. (b) Liu, Z.; Yasseri, A. A.; Lindsey, J. S.; Bocian, D. F. Science 2003, 302, 1543-1545.
3. Balakumar, A.; Lysenko, A. B.; Carcel, C.; Malinovskii, V. L.; Gryko, D. T.; Schweikart, K.-H.; Loewe, R. S.; Yasseri, A. A.; Liu, Z.; Bocian, D. F.; Lindsey, J. S. J. Org. Chem. 2004, 69, 1435-1443.
4. Muthukumaran, K.; Loewe, R. S.; Ambroise, A.; Tamaru, S.-I.; Li, Q.; Mathur, G.; Bocian, D. F.; Misra, V.; Lindsey, J. S. J. Org. Chem. 2004, 69, 1444-1452.
5. Loewe, R. S.; Ambroise, A.; Muthukumaran, K.; Padmaja, K.; Lysenko, A. B.; Mathur, G.; Li, Q.; Bocian, D. F.; Misra, V.; Lindsey, J. S. J. Org. Chem. 2004, 69, 1453-1460.
6. Wei, L.; Padmaja, K.; Youngblood, W. J.; Lysenko, A. B.; Lindsey, J. S.; Bocian, D. F. J. Org. Chem. 2004, 69, 1461-1469.
7. Liu, Z.; Yasseri, A. A.; Loewe, R. S.; Lysenko, A. B.; Malinovskii, V. L.; Zhao, Q.; Surthi, S.; Li, Q.; Misra, V.; Lindsey, J. S.; Bocian, D. F. J. Org. Chem. 2004, 69, 5568-5577.
8. Lysenko, A. B.; Malinovskii, V. L.; Kisari, P.; Wei, L.; Diers, J. R.; Bocian, D. F.; Lindsey, J. S. J. Porphyrins Phthalocyanines 2005, 9, 491-508.
9. Padmaja, K.; Wei, L.; Lindsey, J. S.; Bocian, D. F. J. Org. Chem. 2005, 70, 7972-7278.
10. Thamyongkit, P.; Yu, L.; Padmaja, K.; Jiao, J.; Bocian, D. F.; Lindsey, J. S. J. Org. Chem. 2006, 71, 1156-1171.
11. Schmidt, I.; Jiao, J.; Thamyongkit, P.; Sharada, D. S.; Bocian, D. F.; Lindsey, J. S. J. Org. Chem. 2006, 71, 3033-3050.
12. Roth, K. M.; Yasseri, A. A.; Liu, Z.; Dabke, R. B.; Malinovskii, V.; Schweikart, K.-H.; Yu, L.; Tiznado, H.; Zaera, F.; Lindsey, J. S.; Kuhr, W. G.; Bocian, D. F. J. Am. Chem. Soc. 2003, 125, 505-517.
13. Liu, Z.; Schmidt, I.; Thamyongkit, P.; Loewe, R. S.; Sykomin, D.; Diers, J. R.; Zhao, Q.; Misra, V.; Lindsey, J. S.; Bocian, D. F. Chem. Mater. 2005, 17, 3728-3742.
14. (a) Mandelman, J. A.; Dennard, R. H.; Bronner, G. B.; DeBrosse, J. K.; Divakaruni, R.; Li, Y.; Radens, C. J. IBM J. Res. Dev. 2002, 46, 187-212.
15. (b) Kuhr, W. G.; Gallo, A. R.; Manning, R. W.; Rhodine, C. W. Mater. Res. Soc. Bull. 2004, 838-842.
16. (a) Vioux, A.; Le Bideau, J.; Mutin, P. H.; Leclercq, D. Top. Curr. Chem. 2004, 232, 145-174.
17. (b) Multilayer Thin Films; Decher, G., Schlenoff, J. B., Eds.; Wiley-VCH: Weinheim, 2002.
18. (c) Manne, S.; Aksay, I. A. Curr. Opin. Solid State Mater. Sci. 1997, 2, 358-364.
19. (d) Tredgold, R. H. Order in Thin Organic Films; Cambridge University Press: Cambridge, UK, 1994.
20. (e) Cao, G.; Hong, H.-G.; Mallouk, T. E. Acc. Chem. Res. 1992, 25, 420-427.
21. (f) Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: Boston, 1991.
22. (a) Leskelä, M.; Ritala, M. Angew. Chem., Int. Ed. 2003, 42, 5548-5554.
23. (b) Lim, B. S.; Rahtu, A.; Gordon, R. G. Nat. Mater. 2003, 2, 749-754.
24. (a) Major, J. S.; Blanchard, G. J. Chem. Mater. 2002, 14, 2574-2581.
25. (b) Kohli, P.; Blanchard, G. J. Langmuir 2000, 16, 8518-8524.
26. (a) Xie, W.; Pan, W.-P.; Chuang, K. C. Thermochim. Acta 2001, 367-368, 143-153.
27. (b) Cella, J. A. Polym. Degrad. Stab. 1992, 36, 99-110.
28. Anariba, F.; DuVall, S. H.; McCreery, R. L. Anal. Chem. 2003, 75, 3837-3844.
29. (a) Li, X. Y.; Czernuszewicz, R. S.; Kincaid, J. R.; Su, Y. O.; Spiro, T. G. J. Phys. Chem. 1990, 94, 31-47.
30. (b) Li, X. Y.; Czernuszewicz, R. S.; Kincaid, J. R.; Spiro, T. G. J. Am. Chem. Soc. 1989, 111, 7012-7023.
31. Silverstein, R. M.; Bassler, G. C. Spectrophotometric Identification of Organic Compounds; Wiley: New York, 1967.
32. Hase, Y.; Davanzo, C. U.; Kawai, K.; Sala, O. J. Mol. Struct. 1976, 30, 37-44.
33. (a) Debe, M. K. J. Vac. Sci. Technol. 1982, 2l, 74-79.
34. (b) Tsai, W. H.; Boerio, F. J.; Jackson, K. M. Langmuir 1992, 8, 1443-1450.
35. Polyimides: Fundamentals and Applications; Ghosh, M. K., Mittal, K. L., Eds.; Marcel Dekker: New York, 1996.
36. (a) Greenler, R. G. J. Chem. Phys. 1966, 44, 310-315.
37. (b) Allara, D. L.; Nuzzo, R. G. Langmuir 1985, 1, 52-66.
38. (c) Zaera, F. Int. Rev. Phys. Chem. 2002, 21, 433-471.
39. Polzonetti, G.; Ferri, A.; Russo, M. V.; Iucci, G.; Licoccia, S.; Paolesse, R. J. Vac. Sci. Technol., A 1999, 17, 832-839.
40. Zhang, Z.; Hu, R.; Liu, Z. Langmuir 2000, 16, 1158-1162.
41. (a) Yasseri, A. A.; Syomin, D.; Malinovskii, V.; Loewe, R. S.; Lindsey, J. S.; Zaera, F.; Bocian, D. F. J. Am. Chem. Soc. 2004, 126, 11944-11953.
42. (b) Yasseri, A. A.; Sykomin, D.; Loewe, R. S.; Lindsey, J. S.; Zaera, F.; Bocian, D. F. J. Am. Chem. Soc. 2004, 126, 15603-15612.
43. (c) Wei, L.; Tiznado, H.; Liu, G.; Padmaja, K.; Lindsey, J. S.; Zaera, F.; Bocian, D. F. J. Phys. Chem. B 2005, 109, 23963-23971.
44. Wagner, C. D.; Riggs, W. M.; Davis, L. E.; Moulder, J. F.; Muilenberg, G. E.; Handbook of X-ray Photoelectron Spectroscopy; Perkin-Elmer Corp.: Eden Prairie MN, 1978.
45. Paynter, R. W. Surf. Interface Anal. 1981, 3, 186-187.
46. Boekl, M. S.; Bramblett, A. L.; Hauch, K. D.; Sasaki, T.; Ratner, B. D.; Rogers, J. W., Jr. Langmuir 2000, 16, 5644-5653.
47. Plausibly the similar charge densities observed upon addition of the second porphyrin to the base layer formed from 1 and the version of 1 containing the methyl-flanked amino group arise from compensating effects wherein more of the latter porphyrin is correctly oriented, but formation of the first imide (via reaction with BPTC) is impeded owing to steric constraints from the methyl groups flanking the amino group on the base porphyrin. An argument against this interpretation is that imide formation between the P-Ix layer and either 2 or 3 appears to be quantitative and yields dyad films of similar charge density (Table 1).