The design and synthesis of porphyrin/oligiothiophene hybrid monomers

Organic and Biomolecular Chemistry

Volumn 3, Issue 11, 2005, Pages 2075-2084

  Collis, Gavin E ^a   Campbell, Wayne M ^b   Officer, David L ^b   Burrell, Anthony K ^a  

^a LOS ALAMOS NATIONAL LABORATORY   (United States)

^b MASSEY UNIVERSITY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONDENSATION; MATERIALS SCIENCE; MONOMERS; PHOTOVOLTAIC CELLS; STRUCTURE (COMPOSITION); SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ELECTROCATALYSIS; ELECTROCHROMICS; INHERENTLY CONDUCTING POLYMERS (ICP); PHOTOENERGY CONVERSION;

PORPHYRINS;

EID: 20844446099     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b502517f     Document Type: Article

References (74)

1. For reviews on applications of functionalised conducting polymers, see: (a) J. Roncali, Chem. Rev., 1997, 97, 173;
2. (b) L. M. Goldenberg, M. R. Bryce and M. C. Petty, J. Mater. Chem., 1999, 9, 1957;
3. (c) J. Roncali, J. Mater. Chem., 1999, 9, 1875;
4. (d) D. T. McQuade, A. E. Pullen and T. M. Swager;, Chem. Rev., 2000, 100, 2537;
5. (e) M. O. Wolf, Adv. Mater., 2001, 13(8), 545.
6. P. Gomez-Romero, Adv. Mater., 2001, 13, 163.
7. (a) A. Hagfeldt and M. Grätzel, Acc. Chem. Res., 2000, 33, 269;
8. (b) M. Grätzel, J. Photochem. Photobiol. C, 2003, 4, 145.
9. For some representative examples: (a) C. J. Brabec, S. E. Shaheen, C. Winder, N. S. Sariciftci and P. Denk, Appl. Phys. Lett., 2002, 80(7), 1288;
10. (b) E. Palomares, J. N. Clifford, S. A. Haque, T. Lutz and J. R. Durrant, Chem. Commun., 2002, 1464;
11. (c) S. A. Haque, E. Palomares, H. M. Upadhyaya, L. Otley, R. J. Potter, A. B. Holmes and J. R. Durrant, Chem. Commun., 2003, 3008;
12. (d) T. Hasobe, H. Imahori, S. Fukuzumi and P. V. Kamat, J. Mater. Chem., 2003, 13, 2515;
13. (e) S. E. Shaheen, C. J. Brabec, N. S. Sariciftci, F. Padinger, T. Fromherz and J. Hummelen, Appl. Phys. Lett., 2001, 78(6), 841;
14. (f) F. L. Zhang, M. Johansson, M. R. Andersson, J. C. Hummelen and O. Inganas, Synth. Met., 2003, 137, 1401;
15. (g) M. Granström, K. Petritsch, A. C. Arias, A. Lux, M. R. Andersson and R. H. Friend, Nature, 1998, 395, 257;
16. (h) G. Yu, J. Gao, J. C. Hummelen, F. Wudl and A. J. Heeger, Science, 1995, 270, 1789.
17. (a) H. Segawa, N. Nakayama and T. Shimidzu, J. Chem. Soc., Chem. Commun., 1992, 784;
18. (b) H. Segawa, F.-P. Wu, N. Nakayama, H. Maruyama, S. Sagisaka, N. Higuchi, M. Fujitsuka and T. Shimidzu, Synth. Met., 1995, 71, 2151;
19. (c) T. Shimidzu, Synth. Met., 1996, 81, 235.
20. (a) A. Yassar, M. Hmyene, D. C. Loveday and J. P. Ferraris, Synth. Met., 1997, 84, 231;
21. (b) A. Cravino, G. Zerza, H. Neugebauer, M. Maggini, S. Bucella, E. Menna, M. Svensson, M. R. Andersson, C. J. Brabec and N. S. Sariciftci, J. Phys. Chem. B, 2002, 106, 70;
22. (c) Y. Murata, M. Suzuki and K. Komatsu, Org. Biomol. Chem., 2003, 1, 2624.
23. (a) Y. Greenwald, G. Cohen, J. Poplawski, E. Ehrenfreund, S. Speiser and D. Davidov, J. Am. Chem. Soc., 1996, 118, 2980;
24. (b) C. A. Cutler, A. K. Burrell, G. E. Collis, P. C. Dastoor, D. L. Officer, C. O. Too and G. G. Wallace, Synth. Met., 2001, 123, 225;
25. (c) G. Casalbore-Miceli, N. Camaioni, M. C. Gallazzi, L. Albertin, A. M. Fichera, A. Geri and E. M. Girotto, Synth. Met., 2002, 125, 307;
26. (d) G. Casalbore-Miceli, M. C. Gallazzi, S. Zecchin, N. Camaioni, A. Geri and C. Bertarelli, Adv. Funct. Mater., 2003, 13(4), 307.
27. (a) T. Yamamoto, N. Fukushima, H. Nakajima, T. Maruyama and I. Yamaguchi, Macromolecules, 2000, 33, 5988;
28. (b) G. Li, T. Wang, A. Schulz, S. Bhosale, M. Lauer, P. Espindola, J. Heinze and J.-H. Fuhrhop, Chem. Commun., 2004, 552.
29. (a) A. K. Burrell and D. L. Officer, Synlett, 1998, 12, 1297;
30. (b) A. K. Burrell and M. R. Wasielewski, J. Porphyrins Phthalocyanines, 2000, 4, 401;
31. (c) E. E. Bonfantini, A. K. Burrell, W. M. Campbell, M. J. Crossley, J. J. Gosper, M. M. Harding, D. L. Officer and D. C. W. Reid, J. Porphyrins Phthalocyanines, 2002, 6(11-12), 708;
32. (d) W. M. Campbell, A. K. Burrell, D. L. Officer and K. W. Jolley, Coord. Chem. Rev., 2004, 248, 817.
33. (a) G. E. Collis, A. K. Burrell and D. L. Officer, Tetrahedron Lett., 2001, 42(49), 8733;
34. (b) J. Chen, A. K. Burrell, G. E. Collis, D. L. Officer, G. F. Swiegers, C. O. Too and G. G. Wallace, Electrochim. Acta, 2002, 47, 2715;
35. (c) G. E. Collis, S. M. Scott, D. L. Officer and A. K. Burrell, J. Org. Chem., 2003, 68(23), 8974;
36. (d) A. K. Burrell, J. Chen, G. E. Collis, D. K. Grant, D. L. Officer, C. O. Too and G. G. Wallace, Synth. Met., 2003, 135-136, 97.
37. (a) J. Roncali, Chem. Rev., 1992, 92, 711;
38. (b) R. D. McCullough, Adv. Mater., 1998, 10(2), 93.
39. (a) B. Ballarin, S. Masiero, R. Seeber and D. Tonelli, J. Electroanal. Chem., 1998, 449, 173;
40. (b) M. SchäferlingandP.Bäuerle, Synth. Met., 1999,101,38;
41. (c) B. Ballarin, R. Seeber, L. Tassi and D. Tonelli, Synth. Met., 2000, 114, 279;
42. (d) M. Schäferling and P. Bäuerle, Synth. Met., 2001, 119, 289.
43. M. J. Crossley and J. K. Prashar, Tetrahedron Lett., 1997, 38(38), 6751.
44. (a) J. R. Smith, S. A. Campbell, N. M. Ratcliffe and M. Dunleavy, Synth. Met., 1994, 63, 233;
45. (b) C. A. Cutler, A. K. Burrell, D. L. Officer, C. O. Too and G. G. Wallace, Synth. Met., 2002, 128, 35.
46. S. Shanmugathasan, C. Edwards and R. W. Boyle, Tetrahedron, 2000, 56, 1025.
47. (a) K. Nagai, T. lyoda, A. FujishimaandK. Hashimoto, Synth. Met., 1997, 85, 1701;
48. (b) M. Kelemen, C. Wachter, H. Winter, E. Dormann, R. Gompper and D. Hermann, Mol. Phys., 1997, 90(3), 407;
49. (c) N. Ono, H. Miyagawa, T. Ueta, T. Ogawa and H. Tani, J. Chem. Soc., Perkin Trans. 1, 1998, 1595;
50. (d) P. Bhyrappa and P. Bhavana, Chem. Phys. Lett., 2001, 349, 399.
51. For example: (a) A. D. Alder, F. R. Longo, J. D. Finarelli, J. Goldmacher, J. Assour and L. Korsakoff, J. Org. Chem., 1967, 32, 476;
52. (b) J. S. Lindsey, H. C. Hsu and I. C. Schreiman, Tetrahedron Lett., 1986, 27(41), 4969;
53. (c) J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827.
54. Porphyrins and Metalloporphyrins (2nd edn.), ed. K. M. Smith, Elsevier, Amsterdam, 1975.
55. G. P. Arsenault, E. Bullock and S. F. MacDonald, J. Am. Chem. Soc., 1960, 82, 4384.
56. Y. L. S.-T. Armiger and T. D. Lash, J. Heterocyd. Chem., 1992, 29, 523.
57. K. M. Kadish, M. Lin, E. Van Caemelbecke, G. De Stefane, C. J. Medforth, D. J. Nurco, N. Y. Nelson, B. Krattinger, C. M. Muzzi, L. Jaquinod, Y. Xu, D. C. Shyr, K. M. Smith and J. A. Shelnutt, Inorg. Chem., 2002, 41, 6673.
58. D.-F. Shi and R. T. Wheelhouse, Tetrahedron Lett., 2002, 43, 9341.
59. (a) V. N. Kalinin, Synthesis, 1992, 5, 413;
60. (b) S. P. Stanforth, Tetrahedron, 1998, 54, 263.
61. R. F. Beeston, S. E. Stitzel and M. A. Rhea, J. Chem. Educ., 1997, 74(12), 1468.
62. For example:(a) M. J. Gunter and L. N. Mander, J. Org. Chem., 1981, 46, 4792;
63. (b) R. A. Freitag, J. A. Mercer-Smith and D. G. Whitten, J. Am. Chem. Soc., 1981, 103, 1226;
64. (c) J. L. Sessler, J. Hugdahl and M. R. Johnson, J. Org. Chem., 1986, 51, 2838;
65. (d) Y. Aoyama, T. Kamohara, A. Yamagishi, H. Toi and H. Ogoshi, Tetrahedron Lett., 1987, 28(19), 2143;
66. (e) M. J. Crossley, L. D. Field, A. J. Forster, M. M. Harding and S. Sternhell, J. Am. Chem. Soc., 1987, 109, 341;
67. (f) J. L. Sessler, M. R. Johnson, S. E. Creager, J. C. Fettinger and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 9310;
68. (g) J. E. Redman and J. K. M. Sanders, Org. Lett., 2000, 2(26), 4141.
69. To explain the concept of atropisomers, the symbol β refers to the 4″-protons that lie above the plane of the porphyrin ring, while α. denotes those that lie below the ring.
70. G. E. Collis, N. R. Evans, A. K. Burrell and D. L. Officer, unpublished results.
71. C. O. Too, G. G. Wallace, A. K. Burrell, G. E. Collis, D. L. Officer, E. W. Boge, S. G. Brodie and E. J. Evans, Synth. Met., 2001, 123, 53.
72. J. Chen, A. K. Burrell, W. M. Campbell, D. L. Officer, C. O. Too and G. G. Wallace, Electrochim. Acta, 2004, 49, 329.
73. (a) D. D. Perrin and W. L. F. Armarego, Purification of Laboratory Chemicals (3rd edn.), Pergamon Press, Oxford, 1988;
74. (b) A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen and F. J. Timmers, Organometallics, 1996, 15, 1518.