Palladium-catalysed synthesis of monodisperse, controlled-length, and functionalized oligoanilines

Journal of the American Chemical Society

Volumn 120, Issue 20, 1998, Pages 4960-4976

  Sadighi, Joseph P ^a   Singer, Robert A ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; PALLADIUM;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; CATALYSIS; POTENTIOMETRY; SYNTHESIS;

EID: 0032572099     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980052c     Document Type: Article

References (64)

1. Fritsche, J. J. Prakt. Chem. 1840, 20, 453-459.
2. (a) Parini, V. P.; Kazakova, Z. S.; Berlin, A. A. Vysokomolekul Soedin. 1961, 3, 1870-1873.
3. (b) Pohl, H. A.; Engelhardt, E. H. J. Phys. Chem. 1962, 66, 2085-2095.
4. (a) Huang, W.-S.; Humphrey, B. D.; MacDiarmid, A. G. J. Chem. Soc., Faraday Trans. 1 1986, 82, 2385-2400.
5. (b) Chen, S.-A.; Fang, W.-G. Macromolecules 1991, 24, 1242-1248.
6. Paul, E. W.; Ricco, A. J.; Wrighton, M. S. J. Phys. Chem. 1985, 89, 1441-1447.
7. Chiang, J.-C.; MacDiarmid, A. G. Synth. Met. 1986, 13, 193-205.
8. Diaz, A. F.; Logan, J. A. J. Electroanal. Chem. Interfacial Electrochem. 1980, 111, 111-114.
9. (a) Cao, Y.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91-97.
10. (b) Cao, Y.; Smith, P.; Heeger, A. J. Synth. Met. 1993, 57, 3514-3519.
11. (c) Pron, A.; Österholm, J. E.; Smith, P.; Heeger, A. J.; Laska, J.; Zagorska, M. Synth. Met. 1993, 57, 3520-3525.
12. MacDiarmid, A. G.; Mu, S.-L.; Somasiri, N. L. D.; Wu, W. Mol. Cryst. Liq. Cryst. 1985, 121, 187-190.
13. '(9) Kobayashi, T.; Yoneyama, H.; Tamura. H. J. Electroanal. Chem. Interfacial Electrochem. 1984, 161, 419-423.
14. (a) Kaneto, K.; Kaneko, M.; Min, Y.; MacDiarmid, A. G. Synth. Met. 1995, 71, 2211-2213.
15. (b) Takashima, W.; Kaneko, M.; Kaneto, K.; MacDiarmid, A. G. Synth. Met. 1995, 71, 2265-2266.
16. (a) DeBerry, D. W. J. Electrochem. Soc. 1985, 132, 1022-1026.
17. (b) Ahmad, N.; MacDiarmid, A. G. Synth. Met. 1996, 78, 103-110.
18. (c) Lu, W.-K.; Elsenbaumer, R. L.; Wessling, B. Synth. Met. 1995, 71, 2163-2166.
19. (a) Taka, T. Synth. Met. 1991, 41, 1177-1180.
20. (b) Colaneri, N. F.; Shacklette L. W. IEEE Trans. Instrum. Meas. 1992, 41, 291-297.
21. (c) Joo, J.; Epstein, A. J. Appl. Phys. Lett. 1994, 65, 2278-2280.
22. Honzl, J.; Tlustáková, M. J. Polym. Sci. 1968, C22, 451-462.
23. Willstätter, R.; Moore, C. W. Chem. Ber. 1907, 40, 2665-2689.
24. Lu, F.-L.; Wudl, F.; Nowak, M.; Heeger, A. J. J. Am. Chem. Soc. 1986, 108, 8311-8313.
25. Ochi, M.; Furusho, H.; Tanaka, J. Bull. Chem. Soc. Jpn. 1994, 67, 1749-1752.
26. Rebourt, E.; Joule, J. A.; Monkman, A. P. Synth. Met. 1997, 84, 65-66.
27. Zhang, W. J.; Feng, J.; MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1997, 84, 119-120.
28. (a) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927-928.
29. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
30. (c) Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546.
31. (d) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
32. (e) Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7241.
33. (f) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612.
34. (g) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
35. (h) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267.
36. (j) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273.
37. (k) Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359-6362.
38. (1) Åhman, J.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6363-6366.
39. (m) Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367-6370.
40. For a review of synthetic approaches to conjugated macromolecules with precise length, see: Tour, J. M. Chem. Rev. 1996, 96, 537-553.
41. For the first example of a divergent-convergent synthesis used to prepare monodisperse polyethylenes, see: Igner, E.; Paynter, O. I.; Simmonds, D. J.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 1 1987, 2447-2454.
42. For a review of electrophilic substitutions of arylsilanes, see: Bennetau, B.; Dunogues, J. Synlett 1993, 171-176.
43. Wessjohann, L.; McGaffin, G.; de Meijere, A. Synthesis 1989, 359-363.
44. Fasth, K.-J.; Antoni, G.; Långström, B. J. Chem. Soc., Perkin Trans. 1 1988, 3081-3084.
45. This compound had been obtained previously by an analogous sequence using 4-bromo-N,N-bis(trimethylsilyl)aniline: Walton, D. R. M. J. Chem. Soc. C 1966, 1706-1707. We found it more convenient to use the crystalline and moisture-stable N-(diphenylmethylene)-4-bromoaniline.
46. For reasons of availability at the time that this work was carried out, we employed S-BINAP. The significantly less expensive racemic form, now available commercially from Strem Chemical Company, is an equally effective ligand in these coupling reactions, with no observable differences in yields.
47. 3-diamine, a core piece for odd-numbered oligomers, has been prepared: see ref 19m.
48. Berthelot, J.; Guette, C.; Essayegh, M.; Desbene, P. L.; Basselier, J. J. Synth. Commun. 1986, 16, 1641-1645.
49. Thermal deprotection of BOC-protected pyrroles and indoles has been reported to proceed more rapidly: Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 19-28.
50. Removal of benzyl and tert-butyl carbamate groups from peptides using TMSI is well-known: Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495-496.
51. Ofer, D.; Crooks, R. M.; Wrighton, M. S. J. Am. Chem. Soc. 1990, 112, 7869-7879. For other discussions of polyaniline oxidation states, see: refs 3-5.
52. 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, 3677-3684.
53. Early studies described a "nigraniline" oxidation state in polyaniline. Described as an intermediate between emeraldine and pernigraniline, it may well have been a mixture of the two. This possibility was not discussed, and the evidence was inconclusive: (a) Willstätter, R.; Dorogi, S. Chem. Ber. 1909, 42, 2147-2168. (b) Willstätter, R.; Dorogi, S. Chem. Ber. 1909, 42, 4118-4135. (c) Green, A. G.; Woodhead, A. E. J. Chem. Soc. 1910, 97, 2388-2403. (d) Green, A. G.; Woodhead, A. E. J. Chem. Soc. 1912, 101, 1117-1123.
54. Early studies described a "nigraniline" oxidation state in polyaniline. Described as an intermediate between emeraldine and pernigraniline, it may well have been a mixture of the two. This possibility was not discussed, and the evidence was inconclusive: (a) Willstätter, R.; Dorogi, S. Chem. Ber. 1909, 42, 2147-2168. (b) Willstätter, R.; Dorogi, S. Chem. Ber. 1909, 42, 4118-4135. (c) Green, A. G.; Woodhead, A. E. J. Chem. Soc. 1910, 97, 2388-2403. (d) Green, A. G.; Woodhead, A. E. J. Chem. Soc. 1912, 101, 1117-1123.
55. Early studies described a "nigraniline" oxidation state in polyaniline. Described as an intermediate between emeraldine and pernigraniline, it may well have been a mixture of the two. This possibility was not discussed, and the evidence was inconclusive: (a) Willstätter, R.; Dorogi, S. Chem. Ber. 1909, 42, 2147-2168. (b) Willstätter, R.; Dorogi, S. Chem. Ber. 1909, 42, 4118-4135. (c) Green, A. G.; Woodhead, A. E. J. Chem. Soc. 1910, 97, 2388-2403. (d) Green, A. G.; Woodhead, A. E. J. Chem. Soc. 1912, 101, 1117-1123.
56. Early studies described a "nigraniline" oxidation state in polyaniline. Described as an intermediate between emeraldine and pernigraniline, it may well have been a mixture of the two. This possibility was not discussed, and the evidence was inconclusive: (a) Willstätter, R.; Dorogi, S. Chem. Ber. 1909, 42, 2147-2168. (b) Willstätter, R.; Dorogi, S. Chem. Ber. 1909, 42, 4118-4135. (c) Green, A. G.; Woodhead, A. E. J. Chem. Soc. 1910, 97, 2388-2403. (d) Green, A. G.; Woodhead, A. E. J. Chem. Soc. 1912, 101, 1117-1123.
57. For a review of π-dimers and π-stacks in conducting polymers, see: Miller, L. L.; Mann, K. R. Acc. Chem. Res. 1996, 29, 417-423.
58. The indium-tin oxide coating is known to be unstable to strong acids; however, immersion of the slides in 1.0 M sulfuric acid, for the short time periods involved in these CV studies, caused no discernible degradation.
59. The cause of this material loss is unclear. It is possible that the evolution of carbon dioxide during hydrolysis causes blistering of the films, with some initial physical instability.
60. Some ambiguity is involved in assigning the peak areas, but the first peak is clearly larger, in the CVs of both the heptaaniline and the decaaniline, for any reasonable choice of demarcation. The narrow peak at high potential is smaller than it appears.
61. Carbazole itself undergoes anodic oxidation at +1.16 V relative to SCE: Ambrose, J. F.; Nelson, R. F. J. Electrochem. Soc. 1968, 115, 1159-1164. Conjugation of the carbazole moiety with a protonated iminoquinone might well raise the oxidation potential beyond the range investigated here.
62. Taguchi, K.; Westheimer, F. H. J. Org. Chem. 1971, 36, 1570-1572.
63. This reaction is carried out under argon; we note that, under air, palladium on carbon may ignite upon contact with methanol. Once started, the imine hydrogenolysis reaction does not require rigorously air-free conditions.
64. Seitz, D. E.; Ferreira, L. Synth. Commun. 1979, 931-939.