Extensive quinoidal oligothiophenes with dicyanomethylene groups at terminal positions as highly amphoteric redox molecules

Journal of the American Chemical Society

Volumn 127, Issue 25, 2005, Pages 8928-8929

  Takahashi, Toshiaki ^a   Matsuoka, Ken Ichi ^a   Takimiya, Kazuo ^a   Otsubo, Tetsuo ^a   Aso, Yoshio ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; DICYANOMETHYLENE; OLIGOTHIOPHENE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; ELECTRIC FIELD; ELECTRON; EXCITATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SEMICONDUCTOR; SOLUBILITY; VIBRATION;

METHANE; MOLECULAR STRUCTURE; NITRILES; OXIDATION-REDUCTION; QUINONES; THIOPHENES;

EID: 21244464227     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051840m     Document Type: Article

References (23)

1. Gronowitz, S.; Uppström. B. Acta Chem. Scand. B 1974, 28, 981-985.
2. (a) Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. J. Chem. Soc., Chem. Commun. 1987, 1816-1817.
3. (b) Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539-1546.
4. (a) Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Chem. Lett. 1988, 1179-1182.
5. (b) Yui, K.; Ishida, H.; Aso, Y.; Otsubo, T.; Ogura, F.; Kawamoto, A.; Tanaka, J. Bull. Chem. Soc. Jpn. 1989, 62, 1547-1555.
6. (c) Ishida, H.; Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1990, 63, 2828-2835.
7. (d) Fujii, M.; Aso, Y.; Otsubo, T.; Ogura, F. Synth. Met. 1993, 56, 2136-2139.
8. (e) Yoshida, S.; Fujii, M.; Aso, Y.; Otsubo, T.; Ogura, F. J. Org. Chem. 1994, 59, 3077-3081.
9. Higuchi, H.; Nakayama, T.; Koyama, H.; Ojima, J.; Wada, T.; Sasabe, H. Bull. Chem. Soc. Jpn. 1995, 68, 2363-2377.
10. (a) Pappenfus, T. M.; Chesterfield, R. J.; Frisbie, C. D.; Mann, K. R.; Casado, J.; Raff, J. D.; Miller, L. L. J. Am. Chem. Soc. 2002, 124, 4184-4185.
11. (b) Pappenfus, T. M.; Raff, J. D.; Hukkanen, E. J.; Burney, J. R.; Casado, J.; Drew, S. M.; Miller, L. L.; Mann, K. R. J. Org. Chem. 2002, 67, 6015-6024.
12. (c) Chesterfield, R. J.; Newman, C. R.; Pappenfus, T. M.; Ewbank, P. C.; Haukaas, M. H.; Mann, K. R.; Miller, L. L.; Frisbie, C. D. Adv. Mater. 2003, 15, 1278-1282.
13. Izumi, T.; Kobashi, S.; Takimiya, K.; Aso, Y.; Otsubo, T. J. Am. Chem. Soc. 2003, 125, 5286-5287.
14. Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 932-933.
15. Tsuda, A.; Osuka, A. Science 2001, 293, 79-82.
16. Inoue, S.; Aso, Y.; Otsubo, T. Chem. Commun. 1997, 1105-1106.
17. (a) Fabian, J.; Zahradník. R. Angew. Chem., Int. Ed. Engl. 1989, 28, 677-694.
18. (b) Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197-1226.
19. Takahashi and Suzuki reported that thienoquinoid-inserted diphenoquinones showed amphoteric behaviors, but the absorption bands are below 900 nm. Takahashi, K.; Suzuki, T. J. Am. Chem. Soc. 1989, 111, 5483-5485.
20. Chappell, J. S.; Bloch, A. N.; Bryden, W. A.; Maxfield, M.; Poehler, T. O.; Cowan, D. O. J. Am. Chem. Soc. 1981, 103, 2442-2443.
21. Montgomery, L. K.; Huffman, J. C.; Jurczak, E. A.; Grendze, M. P. J. Am. Chem. Soc. 1986, 108, 6004-6011 and references therein.
22. (a) Rebmann, A.; Zhou, J.; Schuler, P.; Rieker, A.; Stegmann, H. B. J. Chem. Soc., Perkin Trans. 2 1997, 1615-1617.
23. (b) Hoogmartens, I.; Adriaensens, P.; Vanderzande, D.; Gelan, J.; Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L. Macromolecules 1992, 25, 7347-7356.