Regioregular head-to-tail oligothiophene-functionalized 9,9′-spirobifluorene derivatives. 2. NMR characterization, thermal behaviors, and electrochemical properties

Journal of Organic Chemistry

Volumn 67, Issue 23, 2002, Pages 8104-8113

  Pei, Jian ^a,b   Ni, Jing ^b   Zhou, Xing Hua ^a   Cao, Xiao Yu ^a   Lai, Yee Hing ^b  

^a PEKING UNIVERSITY   (China)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL SHIFTS;

DERIVATIVES; ELECTROCHEMISTRY; ELECTRON ENERGY LEVELS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; ORGANIC SOLVENTS; SOLUBILITY; THERMOANALYSIS;

SULFUR COMPOUNDS;

FLUORENE DERIVATIVE; ORGANIC SOLVENT; SPIRO COMPOUND; THIOPHENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; ENERGY; OXIDATION REDUCTION POTENTIAL; PROTON NUCLEAR MAGNETIC RESONANCE; THERMAL ANALYSIS;

EID: 0037111768     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020397k     Document Type: Article

References (56)

1. (a) Handbook of Conducting Polymers, 2nd Ed.; Skotheim, T. A., Ed.; Dekker: New York, 1997.
2. (b) Conjugated Conducting Polymers; Kies, H., Ed.; Springer: Berlin, 1992; Vol. 102.
3. (c) Conjugated Polymers; Brédas, J. L., Sylbey, R., Eds.; Kluwer: Dordrecht, The Netherlands, 1991.
4. (d) Miller, J. S. Adv. Mater. 1993, 5, 671.
5. (e) Kanatzidis, M. G. Chem. Eng. News 1990, 36.
6. (f) Roncali, J. Chem. Rev. 1992, 92, 711.
7. (g) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402.
8. (a) Plazek, D. J.; Magill, J. H. J. Chem. Phys. 1966, 45, 3038.
9. (b) Greet, R. J.; Turnbull, D. J. Chem. Phys. 1966, 46, 1243.
10. Joswick, M. D.; Campbell, I. H.; Barashkov, N. N.; Ferraris, J. P. J. Appl. Phys. 1996, 80, 2883.
11. (a) Bettenhausen, J.; Strohriegl, P. Adv. Mater. 1996, 8, 507.
12. (b) Shirota, Y.; Kobata, T.; Noma, N. Chem. Lett. 1989, 1145.
13. (a) Wang, P. W.; Liu, Y. J.; Devadoss, C.; Bharathi, P.; Moore, J. S. Adv. Mater. 1996, 8, 237.
14. (b) Louie, J.; Hartwig, J. F.; Fry, A. J. J. Am. Chem. Soc. 1997, 119, 11695.
15. Wang, S.; J. Oldham, W. J.; Hudack, J. R. A.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 5695.
16. (a) Salbeck, J.; Yu, N.; Bauer, J.; Weissörtel, F.; Bestgen, H. Synth. Met. 1997, 91, 209.
17. (b) Salbeck, J.; Weissörtel, F.; Bauer, J. Macromol. Symp. 1998, 125, 121.
18. (a) Naito, K.; Miura, A. J. Phys. Chem. 1993, 97, 6240.
19. (b) Naito, K. Chem. Mater. 1994, 6, 2343.
20. Pei, J.; Ni, J.; Zhou, X.-H.; Cao, X.-Y.; Lai, Y.-H. J. Org. Chem. 2002, 67, 4924.
21. (a) Pelter, A.; Jenkins, I.; Jones, D. E. Tetrahedron 1997, 53, 10357.
22. (b) Zotti, G.; Salmaso, R.; Gallazzi, M. C.; Marin, R. A. Chem. Mater. 1997, 9, 791.
23. (c) Welzel, H.-P.; Kossmehl, G.; Boettcher, H.; Engelmann, G.; Hunnius, W.-D. Macromolecules 1997, 30, 7419.
24. (d) Li, W.; Maddux, T.; Yu, L. Macromolecules 1996, 29, 7329.
25. (a) Pei, J.; Yu, W.-L.; Ni, J.; Lai, Y.-H.; Huang, W.; Heeger, A. L. Macromolecules 2001, 34, 7421.
26. (b) Pei, J.; Yu, W.-L.; Huang, W.; Heeger, A. J. Macromolecules 2000, 33, 2462.
27. (c) Pei, J.; Yu, W.-L.; Huang, W.; Heeger, A. J. Chem. Commun. 2000, 1631.
28. (d) Liu, B.; Yu, W.-L.; Lai, H.-Y.; Huang, W. Macromolecules 2000, 33, 8945.
29. (e) Pei, J.; Yu, W.-L.; Huang, W.; Heeger, A. J. Synth. Met. 1999, 105, 43.
30. (f) Pei, J.; Yu, W.-L.; Huang, W.; Heeger, A. J. Acta Polym. 1999, 50, 327.
31. (a) Kagan, J.; Arora, S. K. J. Org. Chem. 1983, 48, 4317.
32. (b) Han, E. M.; Do, L. M.; Niidome, Y.; Fujihira, M. Chem. Lett. 1994, 969.
33. Steuber, F.; Staudigel, J.; Stóssel, M.; Simmerer, J.; Winnacker, A.; Spreitzer, H.; Weissörtel, F.; Salbeck, J. Adv. Mater. 2000, 12, 130.
34. Ishikawa, W.; Inada, H.; Nakado, H.; Shirota, Y. Mol. Cryst. Liq. Cryst. 1992, 211, 431.
35. (a) Ishikawa, W.; Inada, H.; Nakano, H.; Shirota, Y. Chem. Lett. 1991, 1731.
36. (b) Ueta, E.; Nakano, H.; Shirota, Y. Chem. Lett. 1994, 2397.
37. (c) Nakano, H.; Ueta, E.; Shirota, Y. Mol. Cryst. Liq. Cryst. 1998, 313, 241.
38. (a) Chaloner, P. A.; Hitchcock, P. B.; Gunatunga, S. R. Acta Crystallogr. 1994, C50, 1941.
39. (b) van Bolhuis, F.; Wynberg, H.; Havinga, E. E.; Meijer, E. W.; Staring, E. G. J. Synth. Met. 1989, 30, 381.
40. (c) Porzio, W.; Destri, S.; Mascherpa, M.; Bruckner, S. Acta Polym. 1993, 44, 266.
41. (d) Horowitz, G.; Bachet, B.; Yassar, A. Lang, P.; Demanze, F.; Fave, J. L.; Garnier, F. Chem. Mater. 1995, 7, 1337.
42. (e) Fichou, D.; Bachet, B.; Demanze, F.; Billy, I.; Horowitz, G.; Garnier, F. Adv. Mater. 1996, 8, 500.
43. (a) Hotta, S.; Waragai, K. J. Mater. Chem. 1991, 1, 835.
44. (b) Liao, J. H.; Benz, M.; LeGoff, E.; Kanazidis, M. G. Adv. Mater. 1994, 6, 135.
45. (c) Azumi, R.; Gotz, G.; Bauerle, P. Synth. Met. 1999, 101, 544.
46. (a) Marque, P.; Roncali, J.; Garnier, F. J. Electoanal. Chem. 1987, 218, 107.
47. (b) Hubbard, A. T.; Anson, F. C. Anal. Chem. 1966, 38, 1887.
48. (c) Laviron, E. J. Electroanal. Chem. 1972, 39, 1.
49. Barth, M.; Guilerez, S.; Bidan, G.; Bras, G.; Lapkowski, M. Electrochim. Acta 2000, 45, 4409.
50. (a) Tourillon, G.; Gourier, D.; Garnier, P.; Vivien, D. J. Phys. Chem. 1984, 88, 1049.
51. (b) Fichou, D.; Horowitz, G.; Xu, B.; Garnier, F. Synth. Met. 1990, 39, 243.
52. Guay, J.; Diaz, A.; Wu, R. L.; Tour, J. M. J. Am. Chem. Soc. 1993, 115, 1869.
53. (a) Li, Y. F.; Cao, Y.; Gao, J.; Wang, D. L.; Yu, G.; Heeger, A. J. Synth. Met. 1999, 99, 243.
54. (b) de Leeuw, D. M.; Simenon, M. M. J.; Brown, A. R.; Einerhand, R. E. F. Synth. Met. 1997, 87, 53.
55. (c) Eckhardt, H.; Shacklette, L. W.; Jen, K. Y.; Elsenbaumer, R. L. J. Chem. Phys. 1989, 91, 1303.
56. (d) Cervini, R.; Li, X. C.; Spencer, G. W. C.; Holmes, A. B.; Moratti, S. C.; Friend, R. H. Synth. Met. 1997, 84, 359.