Simple formation of C60 and C60-ferrocene conjugated monolayers anchored onto silicon oxide with five carboxylic acids and their transistor applications

Chemistry of Materials

Volumn 23, Issue 4, 2011, Pages 970-975

  Itoh, Yoshimitsu ^a,d   Kim, Bumjung ^a   Gearba, Raluca I ^b   Tremblay, Noah J ^a   Pindak, Ron ^b   Matsuo, Yutaka ^c,d   Nakamura, Eiichi ^c,d   Nuckolls, Colin ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b BROOKHAVEN NATIONAL LABORATORY   (United States)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO-TERMINATED; CONJUGATED MOLECULES; ELECTRONIC EFFECTS; FERROCENES; FUNCTIONALIZED; IR SPECTROSCOPY; MONOLAYER STRUCTURES; P-TYPE; SILICON OXIDE SURFACES; SIMPLE METHOD; UV-VIS SPECTROSCOPY; X RAY REFLECTIVITY;

CARBOXYLIC ACIDS; CARRIER MOBILITY; IRON COMPOUNDS; MONOLAYERS; ORGANIC POLYMERS; SILICON COMPOUNDS; SILICON OXIDES; ULTRAVIOLET SPECTROSCOPY; X RAY PHOTOELECTRON SPECTROSCOPY;

ELECTRON ENERGY LEVELS;

EID: 79951657930     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/cm1025975     Document Type: Article

References (43)

1. Kroto, H. W.; Heath, J. R.; OBrien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162-163
2. Review: Mirikin, C. A.; Caldwell, W. B. Tetrahedron 1996, 52, 5113-5130
3. Konishi, T.; Ikeda, A.; Shinkai, S. Tetrahedron 2005, 61, 4881-4899
4. Gludi, D. M.; Illescas, B. M.; Atienza, C. M.; Wielopolski, M.; Martin, N. Chem. Soc. Rev. 2009, 38, 1587-1597
5. Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474-1476
6. Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789-1791
7. Haddon, R. C.; Perel, A. S.; Morris, R. C.; Palstra, T. T. M.; Hebard, A. F.; Fleming, R. M. Appl. Phys. Lett. 1995, 67, 121-123
8. Priebe, G.; Pietzak, B.; Könenkamp, R. Appl. Phys. Lett. 1997, 71, 2160-2162
9. Anthopoulos, T. D.; Ramil, A. M.; Sitter, H.; Cölle, M.; Leeuw, D. M. Appl. Phys. Lett. 2006, 89, 213504/1-213504/3
10. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103-1169
11. Ma, H.; Yip, H.-L.; Huang, F.; Jen, A. K.-Y. Adv. Funct. Mater. 2010, 20, 1371-1388
12. 60 derivative monolayer; on gold: Shi, X.; Caldwell, W. B.; Chen, K.; Mirkin, C. A. J. Am. Chem. Soc. 1994, 116, 11598-11599
13. Imahori, H.; Norieda, H.; Yamada, H.; Nishimura, Y.; Yamazaki, I.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 100-110
14. Shirai, Y.; Cheng, L.; Chen, B.; Tour, J. M. J. Am. Chem. Soc. 2006, 128, 13479-13489
15. Chen, T.; Pan, G.-B.; Yan, H.-J.; Wan, L.-J.; Matsuo, Y.; Nakamura, E. J. Phys. Chem. C 2010, 114, 3170-3174
16. Matsuo, Y.; Lacher, S.; Sakamoto, A.; Matsuo, K.; Nakamura, E. J. Phys. Chem. C 2010, 14, 17741-17752
17. On ITO: Yamada, H.; Imahori, H.; Nishimura, Y.; Yamazaki, I.; Ahn, T. K.; Kim, S. K.; Kim, D.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 9129-9139
18. Cho, Y.-J.; Ahn, T. K.; Song, H.; Kim, K. S.; Lee, C. Y.; Seo, W. S.; Lee, K.; Kim, S. K.; Kim, D.; Park, J. T. J. Am. Chem. Soc. 2005, 127, 2380-2381
19. Matsuo, Y.; Kanaizuka, K.; Matsuo, K.; Zhong, Y.-W.; Nakae, T.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5016-5017
20. Matsuo, Y.; Ichiki, T.; Radhakrishnan, S. G.; Guldi, D. M.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 6342-6348
21. For other examples, see review: Bonifazi, D.; Enger, O.; Diederich, F. Chem. Soc. Rev. 2007, 36, 390-414
22. Chupa, J. A.; Xu, S.; Fischetti, R. F.; Strongin, R. M.; McCauley, J. P., Jr.; Smith, A. B., III; Blasie, J. K. J. Am. Chem. Soc. 1993, 115, 4383-4384
23. Tsukruk, V. V. Langmuir 1994, 10, 996-999
24. Tsukruk, V. V. Langmuir 1996, 12, 3905-3911
25. Lee, H.; Jeon, C. Synth. Met. 1997, 86, 2297-2298
26. Wei, T.-X.; Zhai, J.; Ge, J.-H.; Gan, L.-B.; Huang, C.-H.; Luo, G.-B.; Ying, L.-M.; Liu, T.-T.; Zhao, X.-S. Appl. Surf. Sci. 1999, 151, 153-158
27. Wei, T.-X.; Zhai, J.; Ge, J.; Gan, L.-B.; Huang, C.-H.; Luo, G.-B.; Ying, L.-M. J. Colloid Interface Sci. 2000, 222, 262-264
28. Gulino, A.; Bazzano, S.; Condorelli, G. G.; Giuffrida, S.; Mineo, P.; Satriano, C.; Scamporrino, E.; Ventimiglia, G.; Vitalini, D.; Fragalà, I. Chem. Mater. 2005, 17, 1079-1084
29. Park, B.; Paoprasert, P.; In, I.; Zwickey, J.; Colavita, P. E.; Hamers, R. J.; Gopalan, P.; Evans, P. G. Adv. Mater. 2007, 19, 4353-4357
30. Guérin, D.; Lenfant, S.; Godey, S.; Vuillaume, D. J. Mater. Chem. 2010, 20, 2680-2690
31. Xiao, S.; Myers, M.; Miao, Q.; Sanaur, S.; Pang, K.; Steigerwald, M. L.; Nuckolls, C. Angew. Chem., Int. Ed. 2005, 44, 7390-7394
32. Zhong, Y.-W.; Matsuo, Y.; Nakamura, E. Org. Lett. 2006, 8, 1463-1466
33. Gao, Y.; Tang, Z.; Watkins, E.; Majewski, J.; Wang, H.-L. Langmuir 2005, 21, 1416-1423
34. Miao, Q.; Lefenfeld, M.; Nguyen, T. Q.; Siegrist, T.; Kloc, C.; Nuckolls, C. Adv. Mater. 2005, 17, 407-412
35. Haller, I. J. Am. Chem. Soc. 1978, 100, 8050-8055
36. Vandenberg, E. T.; Bertilsson, L.; Liedberg, B.; Uvdal, K.; Erlandsson, R.; Elwing, H.; Lundström, I. J. Colloid Interface Sci. 1991, 147, 103-118
37. Heiney, P. A.; Grüneberg, K.; Fang, J. Langmuir 2000, 16, 2651-2657
38. Hooper, A. E.; Werho, D.; Hopson, T.; Palmer, O. Surf. Interface Anal. 2001, 31, 809-814
39. Kobayashi, S.; Nishikawa, T.; Takenobu, T.; Mori, S.; Shimoda, T.; Mitani, T.; Shimotani, H.; Yoshimoto, N.; Ogawa, S.; Iwasa, Y. Nat. Mater. 2004, 3, 317-322
40. Takeya, J.; Nishikawa, T.; Takenobu, T.; Kobayashi, S.; Iwasa, Y.; Mitani, T.; Goldmann, C.; Krellner, C.; Batlogg, B. Appl. Phys. Lett. 2004, 85, 5078-5080
41. Tremblay, N. J.; Gorodetsky, A. A.; Cox, M. P.; Schiros, T.; Kim, B.; Steiner, R.; Bullard, Z.; Sattler, A.; So, W.-Y.; Itoh, Y.; Toney, M. F.; Ogasawara, H.; Ramirez, A. P.; Kymissis, I.; Steigerwald, M. L.; Nuckolls, C. ChemPhysChem 2010, 11, 799-803
42. Acetic acid layer was prepared using the same method as for the preparation of the monolayer of 1 and 2. The concentration of the acetic acid solution was five times higher than the solution of 1 and 2 to make the concentration of the ́acid́ (number of the -COOH group) same. We consider that the acetic acid makes a salt on APTES surface which prevents from evaporation.
43. Yamamoto, Y.; Zhang, G.; Jin, W.; Fukushima, T.; Ishii, N.; Saeki, A.; Seki, S.; Tagawa, S.; Minari, T.; Tsukagoshi, K.; Aida, T. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 21051-21056