Stable triplet-state di(cation radicals) of a meta-para aniline oligomer by 'acid doping'

Journal of the American Chemical Society

Volumn 118, Issue 43, 1996, Pages 10626-10628

  Wienk, Martijn M ^a   Janssen, René A J ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE;

ARTICLE; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; MOLECULAR DYNAMICS; POLYMERIZATION; QUANTUM CHEMISTRY; SPECTROPHOTOMETRY;

EID: 0029801249     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9616591     Document Type: Article

References (32)

1. (a) Fukotome, H.; Takahasi, I.; Ozaki, M. Chem. Phys. Lett. 1987, 133, 34.
2. (b) Kaisaki, D. A.; Chang, W.; Dougherty, D. A. J. Am. Chem. Soc. 1991, 113, 2764.
3. (c) Tanaka, K.; Ago, H.; Yamabe, T. Synth. Met. 1995, 72, 225.
4. (a) Murray, M. M.; Kaszynski, P.; Kaisaki, D. A.; Chang, W.; Dougherty, D. A. J. Am. Chem. Soc. 1994, 116, 8152.
5. (b) Bushby, R. J.; Ng, K. M. Chem. Commun., 1996, 659.
6. (a) Huang, W. -S.; Humphrey, B. D.; MacDiarmid, A. G. J. Chem. Soc., Faraday Trans. 1 1986, 82, 2385.
7. (b) Wudl, F.; Angus, R. O.; Lu, F. L.; Allemand, P. M.; Vachon, D. J.; Nowak, M.; Liu, Z. X.; Heeger, A. J. J. Am. Chem. Soc. 1987, 109, 3677.
8. (c) MacDiarmid, A. G.; Epstein, A. J. Faraday Discuss. Chem. Soc. 1989, 88, 317.
9. (a) Torrance, J. B.; Oostra, S.; Nazzal, A. Synth. Met. 1987, 19, 709.
10. (b) Yoshizawa, K.; Tanaka, K.; Yamabe, T.; Yamauchi, J. J. Chem. Phys. 1992, 96, 5516.
11. (c) Stickly, K. R.; Blackstock, S. C. J. Am. Chem. Soc. 1994, 116, 11576.
12. (d) Ito, A.; Ohta, K.; Tanaka, K.; Yamabe, T.; Yoshizawa, K. Macromolecules 1995, 28, 5618.
13. (e) Ito, A.; Saito, T.; Tanaka, K.; Yamabe, T. Tetrahedron Lett. 1995, 48, 8809.
14. (f) Sasaki, S.; Iyoda, M. Chem. Lett. 1995, 1011.
15. (g) Nakamura, Y.; Iwamura, H. Bull. Chem. Soc. Jpn. 1993, 66, 3724.
16. (h) Okada, K.; Imakura, T.; Oda, M.; Murai, H.; Baumgarten, M. J. Am. Chem. Soc. 1996, 118, 3047.
17. Wienk, M. M.; Janssen, R. A. J. Chem. Commun. 1996, 267.
18. (a) Wolf, J. F.; Forbes, C. E.; Gould, S.; Shacklette, L. W. J. Electrochem. Soc. 1989, 136, 2887.
19. (b) Moll, T.; Heinze, J. Synth. Met. 1993, 55-57, 1521.
20. 2·2+.
21. (a) Racja, A. Chem. Rev. 1994, 94, 871.
22. (b) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346.
23. (c) Kanno, F. Inoue, K. Koga. N; Iwamura, H. J. Phys. Chem. 1993, 97, 13267.
24. (d) Ling, C., Lahti, P. M. J. Am. Chem. Soc. 1994, 116, 8784.
25. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368.
26. Eberson, L.; Hartshorn, M. P.; Persson, O. Act. Chem. Scand. 1995, 49, 640.
27. Related work on mixed valence in organic molecules see Ref. 4c and (a) Racja, S.; Racja, A. J. Am. Chem. Soc. 1995, 117, 9172. (b) Utamapanya, S.; Racja, A. J. Am. Chem. Soc. 1991, 113, 9242. (c) Bonvoisin, J.; Launay, J.-P.; Rovira, C.; Veciana, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 2106. Matsushita, M.; Nakamura, T.; Momose, T.; Shida, T.; Teki, Y.; Takui, T.; Kinoshita, T.; Itoh, K. J. Am. Chem. Soc. 1992, 114, 9172.
28. Related work on mixed valence in organic molecules see Ref. 4c and (a) Racja, S.; Racja, A. J. Am. Chem. Soc. 1995, 117, 9172. (b) Utamapanya, S.; Racja, A. J. Am. Chem. Soc. 1991, 113, 9242. (c) Bonvoisin, J.; Launay, J.-P.; Rovira, C.; Veciana, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 2106. Matsushita, M.; Nakamura, T.; Momose, T.; Shida, T.; Teki, Y.; Takui, T.; Kinoshita, T.; Itoh, K. J. Am. Chem. Soc. 1992, 114, 9172.
29. Related work on mixed valence in organic molecules see Ref. 4c and (a) Racja, S.; Racja, A. J. Am. Chem. Soc. 1995, 117, 9172. (b) Utamapanya, S.; Racja, A. J. Am. Chem. Soc. 1991, 113, 9242. (c) Bonvoisin, J.; Launay, J.-P.; Rovira, C.; Veciana, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 2106. Matsushita, M.; Nakamura, T.; Momose, T.; Shida, T.; Teki, Y.; Takui, T.; Kinoshita, T.; Itoh, K. J. Am. Chem. Soc. 1992, 114, 9172.
30. Related work on mixed valence in organic molecules see Ref. 4c and (a) Racja, S.; Racja, A. J. Am. Chem. Soc. 1995, 117, 9172. (b) Utamapanya, S.; Racja, A. J. Am. Chem. Soc. 1991, 113, 9242. (c) Bonvoisin, J.; Launay, J.-P.; Rovira, C.; Veciana, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 2106. Matsushita, M.; Nakamura, T.; Momose, T.; Shida, T.; Teki, Y.; Takui, T.; Kinoshita, T.; Itoh, K. J. Am. Chem. Soc. 1992, 114, 9172.
31. 1H NMR spectrum turned out to be very sensitive towards temperature and concentration.
32. Between 160 and 165°C a liquid crystalline phase was observed by polarization microscopy.