Synthesis and electronic properties of series of oligothiophene-[1,10] phenanthrolines

Organic and Biomolecular Chemistry

Volumn 3, Issue 22, 2005, Pages 4143-4152

  Ammann, Martin ^a   Bäuerle, Peter ^a,b  

^a UNIVERSITY OF ULM   (Germany)

^b NOVALED GmbH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; BIOCHEMISTRY; ELECTRONIC PROPERTIES; OPTICAL PROPERTIES; SEMICONDUCTING ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

METAL BINDING SITES; OLIGOTHIOPHENE;

AMINES;

EID: 28444459597     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b508572a     Document Type: Article

References (58)

1. (a) J. M. Tour, Chem. Rev., 1996, 96, 537-553;
2. (b) Electronic Materials: The Oligomer Approach, ed. K. Müllen, G. Wegner, Wiley-VCH, New York, 1998;
3. (c) R. E. Martin and F. Diederich, Angew. Chem., Int. Ed., 1999, 38, 1350-1377.
4. P. Bäuerle, The Synthesis of Oligothiophenes in: Handbook of Oligo-and Polythiophenes, ed. D. Fichou, Wiley-VCH, Weinheim, 1999.
5. U. Mitschke and P. Bäuerle, J. Mater. Chem., 2000, 10, 1471-1507.
6. (a) M. Halik, H. Klauk, U. Zschieschang, G. Schmid, S. Ponomarenko, S. Kirchmeyer and W. Weber, Adv. Mater., 2003, 15, 917-922;
7. (b) F. Würthner, Angew. Chem., Int. Ed., 2001, 40, 1037-1039;
8. (c) F. Gamier, G. Horowitz, X. Peng and D. Fichou, Adv. Mater., 1990, 2, 592-594.
9. H. Hoppe and N. S. Sariciftci, J. Mater. Res., 2004, 19, 1924-1945.
10. (a) L. Antolini, G. Horowitz, F. Kouki and F. Gamier, Adv. Mater., 1998, 10, 382-385;
11. (b) W. Li, H. E. Katz, A. J. Lovinger and J. G. Laquindanum, Chem. Mater., 1999, 11, 458-465;
12. (c) H. Sirringhaus, P. J. Brown, R. H. Friend, K. Bechgaard, B. M. W. Lengeveld-Voss, A. J. H. Spiering, R. A. J. Jannsen, E. W. Meijer, P. Herving and D. M. de Leeuw, Nature, 1999, 401, 685-688.
13. D. Tyler McQuade, A. E. Pullen and T. M. Swager, Chem. Rev., 2000, 100, 2537-2574.
14. (a) M. Rehahn, Acta Polym., 1998, 49, 201-224;
15. (b) P. Nguyen, P. Gómez-Elipe and I. Manners, Chem. Rev., 1999, 99, 1515-1548;
16. (c) B. Lahn and M. Rehahn, Macromol. Symp., 2001, 163, 157-176;
17. (d) U. S. Schubert and C. Eschbaumer, Angew. Chem., Int. Ed., 2002, 41, 2892-2926.
18. P. Coppo, M. Duati, V. N. Kozhevnikov, J. W. Hofstraat and L. De Cola, Angew. Chem., Int. Ed., 2005, 44, 1806-1810.
19. B. J. Holliday and C. A. Mirkin, Angew. Chem., Int. Ed., 2001, 40, 2022-2043 for additional contributions see refs. 154-176 within this article.
20. (a) L. Trouillet, A. De Nicola and S. Guillerez, Chem. Mater., 2000, 12, 1611-1621;
21. (b) K. A. Walters, L. Trouillet, S. Guillerez and K. S. Schanze, Inorg. Chem., 2000, 39, 5496-5509.
22. T. M. Pappenfus and K. R. Mann, Inorg. Chem., 2001, 40, 6301-6307.
23. (a) S. S. Zhu and T. M. Swager, Adv. Mater., 1996, 8, 497-500;
24. (b) S. S. Zhu, R. P. Kingsborough and T. Swager, J. Mater. Chem., 1999, 9, 2123-2131.
25. (a) S. S. Zhu, P. J. Caroll and T. M. Swager, J. Am. Chem. Soc., 1996, 118, 8713-8714;
26. (b) S. S. Zhu and T. M. Swager, J. Am. Chem. Soc., 1997, 119, 12568-12577;
27. (c) J. Buey and T. M. Swager, Angew. Chem., Int. Ed., 2000, 39, 608-612.
28. (a) A. Harriman, A. Mayeux, A. De Nicola and R. Ziessel, Phys. Chem. Chem. Phys., 2002, 4, 2229-2235;
29. (b) C. Ringenbach, A. De Nicola and R. Ziessel, J. Org. Chem., 2003, 68, 4708-4719.
30. J. Hjelm, R. W. Handel, A. Hagfeldt, E. C. Constable, C. E. Housecraft and R. J. Forster, J. Phys. Chem. B, 2003, 107, 10431-10439.
31. T. Yamamoto, Y. Saitoh, K. Anzai, H. Fukumoto, T. Yasuda, Y. Fujiwara, B.-K. Choi, K. Kubota and T. Miyamae, Macromolecules, 2003, 36, 6722-6729.
32. T. Yasuda, I. Yamaguchi and T. Yamamoto, Adv. Mater., 2003, 15, 293-296.
33. G. Bidan, B. Divisia-Blohorn, M. Lapkowski, J. M. Kern and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 5986-5994.
34. P.-L. Vidal, B. Divisia-Blohorn, G. Bidan, J.-L. Hazemann, J.-M. Kern and J.-P. Sauvage, Chem.-Eur. J., 2000, 1663-1673.
35. (a) P.-L. Vidal, M. Billon, B. Divisia-Blohorn, G. Bidan, J.-M. Kern and J.-P. Sauvage, Chem. Commun., 1998, 629-630;
36. (b) P.-L. Vidal, B. Divisia-Blohorn, G. Bidan, J.-M. Kern, J.-P. Sauvage and J.-L. Hazemann, Inorg. Chem., 1999, 38, 4203-4210;
37. (c) J.-P. Sauvage, J.-M. Kern, G. Bidan, B. Divisia-Blohorn and P.-L. Vidal, New J. Chem., 2002, 26, 1287-1290.
38. K. Araki, H. Endo, G. Masuda and T. Ogawa, Chem.-Eur. J., 2004, 10, 3331-3340.
39. M. Ammann, C. A. Schalley, A. Rang and P. Bäuerle, Chem. Eur. J. submitted.
40. C. O. Dietrich-Buchecker, P. A. Marnot and J.-P. Sauvage, Tetrahedron Lett., 1982, 23, 5291-5294.
41. (a) F. Lam, K. S. Chan and B.-J. Liu, Tetrahedron Lett., 1995, 36, 6261-6262;
42. (b) G. B. Bates and D. Parker, Tetrahedron Lett., 1996, 37, 267-270.
43. (a) J. A. Wytko and J. Weiss, J. Org. Chem., 1990, 55, 5200-5202;
44. (b) S. Toyota, C. R. Woods, M. Benaglia and J. S. Siegel, Tetrahedron Lett., 1998, 39, 2697-2700;
45. (c) U. Lüning, M. Abbass and F. Fahrenkrug, Eur. J. Org. Chem., 2002, 3294-3303;
46. (d) M.-J. Blanco, J.-C. Chambron, V. Heitz and J.-P. Sauvage, Org. Lett., 2000, 2, 3051-3054.
47. J. C. Loren and J. S. Siegel, Angew. Chem., 2001, 113, 776-779.
48. (a) J. Lewis and T. D. O'Donoghue, J. Chem. Soc., Dalton Trans., 1980, 736-742;
49. (b) M. Yamada, Y. Nakamura, S. Kuroda and I. Shimao, Bull. Chem. Soc. Jpn., 1990, 63, 2710-2712.
50. (a) M. Bednarz, P. Reineker, E. Mena-Osteritz and P. Bäuerle, J. Lumin., 2004, 110, 225-231;
51. (b) J. Krömer and P. Bäuerle, Tetrahedron, 2001, 57, 3785-3794;
52. (c) J. Krömer, PhD thesis 2000, University of Ulm.
53. N. Armaroli, L. De Cola, V. Balzani, J.-P. Sauvage, C. O. Dietrich-Buchecker and J.-M. Kern, J. Chem. Soc., Faraday Trans., 1992, 88, 553-556.
54. (a) P. Bäuerle, Adv. Mater., 1992, 4, 102-107;
55. (b) J. Seixas de Melo, L. M. Silva, L. G. Arnaut and R. S. Becker, J. Chem. Phys., 1999, 111, 5427-5433.
56. R. Ziessel, P. Bäuerle, M. Ammann, A. Barbieri and F. Barigelletti, Chem. Commun., 2005, 802-804.
57. C. W. Spangler and M. He, J. Chem. Soc., Perkin Trans. 1, 1995, 715-720.
58. C. Wang, M. E. Benz, E. LeGoff, J. L. Schindler, C. R. Kannewurf and M. G. Kanatzidis, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 1993, 34, 422.