Synthesis of 10-nm scale oligothiophene molecular wires bearing anchor units at both terminal positions

Journal of Organic Chemistry

Volumn 72, Issue 7, 2007, Pages 2659-2661

  Endou, Masaru ^a   Ie, Yutaka ^a   Kaneda, Takahiro ^a   Aso, Yoshio ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR WIRES; OLIGOTHIOPHENE;

ELECTROCHEMISTRY; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL);

OLIGOMERS;

OLIGOTHIOPHENE DERIVATIVE; THIOL DERIVATIVE; THIOPHENE DERIVATIVE; TRIMETHYLSILYLETHYNYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; ELECTROCHEMICAL ANALYSIS; MOLECULAR MODEL; SPECTROSCOPY; SYNTHESIS;

EID: 34047241594     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062204p     Document Type: Article

References (45)

1. (a) Feldheim, D. L.; Keating, C. D. Chem. Soc. Rev. 1998, 27, 1-12.
2. (b) Joachim, C.; Gimzewski, J. K.; Aviram, A. Nature 2000, 408, 541-548.
3. (c) Reed, M. A.; Tour, J. M. Sci. Am. 2000, 6, 86-93.
4. (d) Carroll, R. L.; Gorman, C. B. Angew. Chem., Int. Ed. 2002, 41, 4378-4400.
5. (e) Nitzan, A.; Ratner, M. A. Science 2003, 300, 1384-1389.
6. (f) Service, R. F. Science 2003, 302, 556-559.
7. (g) Robertson, N.; McGowan, C. A. Chem. Soc. Rev. 2003, 32, 96-103.
8. (h) McCreery, R. L. Chem. Mater. 2004, 16, 4477-4496.
9. For example, see: (a) James, D. K.; Tour, J. M. Chem. Mater, 2004, 16, 4423-4435.
10. (b) Liang, T.-T.; Naitoh, Y.; Horikawa, M.; Ishida, T.; Mizutani, W. J. Am. Chem. Soc. 2006, 128, 13720-13726 and references therein.
11. (a) Liu, K.; Avouris, P.; Bucchignano, J.; Martel, R.; Sun, S.; Michl, J. Appl. Phys. Lett. 2002, 80, 865-867.
12. (b) Saifullah, M. S. M.; Ondarçuhu, T.; Koltsov, D. K.; Joachim, C.; Weiland, M. E. Nanotechnology 2002, 13, 659-662.
13. (c) Nagase, T.; Kubota, T.; Mashiko, S. Thin Solid Films 2003, 438-439, 374-377.
14. (d) Nagase, T.; Gamo, K.; Kubota, T.; Mashiko, S. Microelectron. Eng. 2005, 78-79, 253-259.
15. (e) Nagase, T.; Gamo, K.; Kubota, T.; Mashiko, S. Thin Solid Films 2006, 499, 279-284.
16. (a) Electronic Materials: The Oligomer Approach; Wegner, G., Müllen, K., Eds.; Wiley-VHC: Weinheim, Germany, 1998.
17. (b) Roncali, J. Acc. Chem. Res. 2000, 33, 147-156.
18. (c) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
19. (d) Segura, J. L.; Martín, N. J. Mater. Chem. 2000, 10, 2403-2435.
20. (e) Robertson, N.; McGowan, C. A. Chem. Soc. Rev. 2003, 32, 96.
21. (a) Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376-1387.
22. (b) Jones, L., II; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410.
23. (c) Xue, C.; Luo, F.-T. J. Org. Chem. 2003, 68, 4417-4421.
24. (d) Wang, C.; Batsanov, A. S.; Bryce, M. R. J. Org. Chem. 2006, 71, 108-116.
25. (e) Tam, I. W.; Yan, J.; Breslow, R. Org. Lett. 2006, 8, 183-185.
26. For recent reviews on oligothiophenes, see: (a) Roncali, J. J. Mater. Chem. 1999, 9, 1875-1893.
27. (b) Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, Germany, 1999.
28. (c) Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359-369.
29. (d) Otsubo, T.; Aso, Y.; Takimiya, K. Bull. Chem. Soc. Jpn. 2001, 74, 1789-1801.
30. (e) Otsubo, T.; Aso, Y.; Takimiya, K. J. Mater. Chem. 2002, 12, 2565-2575.
31. (a) Sumi, N.; Nakanishi, H.; Ueno, S.; Takimiya, K.; Aso, Y.; Otsubo, T. Bull. Chem. Soc. Jpn. 2001, 74, 979-988.
32. (b) Izumi, T.; Kobashi, S.; Takimiya, K.; Aso, Y.; Otsubo, T. J. Am. Chem. Soc. 2003, 125, 5286-5287.
33. (c) Ikemoto, J.; Takimiya, K.; Aso, Y.; Otsubo, T.; Fujitsuka, M.; Ito, O. Org. Lett. 2002, 4, 309-311.
34. (d) Nakamura, T.; Fujitsuka, M.; Araki, Y.; Ito, O.; Ikemoto, J.; Takimiya, K.; Aso, Y.; Otsubo, T. J. Phys. Chem. B 2004, 108, 10700-10710.
35. (a) Tour, J. M.; Jones, L.; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. M.; Allara, D. L.; Parikh, A. N.; Atre, S. J. Am. Chem. Soc. 1995, 117, 9529-9534.
36. (b) Bumm, L. A.; Arnold, J. J.; Cygan, M. T.; Dunbar, T. D.; Burgin, T. P.; Jones, L., II; Allara, D. L.; Tour, J. M.; Weiss, P. S. Science 1996, 271, 1705-1707.
37. (a) Marchenko, A.; Katsonis, N.; Fichou, D.; Aubert, C.; Malacria, M. J. Am. Chem. Soc. 2002, 124, 9998-9999.
38. (b) Katsonis, N.; Marchenko, A.; Taillemite, S.; Fichou, D.; Chouraqui, G.; Aubert, C.; Malacria, M. Chem. Eur. J. 2003, 9, 2574-2581.
39. (c) 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 and references therein.
40. Barrett, A. G. M.; Cramp, S. M.; Hennessy, A. J.; Procopiou, P. A.; Roberts, R. S. Org. Lett. 2001, 3, 271-273.
41. Blanchard, P.; Svenstrup, N.; Becher, J. Chem. Commun. 1996, 615-616.
42. Thiophene 3-mers and 6-mers with thiol groups at both terminal positions have been reported, see: (a) Casado, J.; Katz, H. E.; Hernández, V.; Navarrete, J. T. L. J. Phys. Chem. B 2002, 106, 2488-2496.
43. (b) Sotgiu, G.; Zambianchi, M.; Barbarella, G.; Botta, C. Tetrahedron 2002, 58, 2245-2251.
44. (c) Boer, B.; Meng, H.; Perepichka, D. F.; Zheng, J.; Frank, M. M.; Chabal, Y. J.; Bao, Z. Langmuir 2003, 19, 4272-4284.
45. (d) Yasuda, S.; Yoshida, S.; Sasaki, J.; Okutsu, Y.; Nakamura, T.; Taninaka, A.; Takeuchi, O.; Shigekawa, H. J. Am. Chem. Soc. 2006, 128, 7746-7747.