The synthesis and properties of solution processable phenyl cored thiophene dendrimers

Journal of Materials Chemistry

Volumn 15, Issue 42, 2005, Pages 4518-4528

  Mitchell, William J ^a   Kopidakis, Nikos ^a   Rumbles, Garry ^a   Ginley, David S ^a   Shaheen, Scan E ^a  

^a NATIONAL RENEWABLE ENERGY LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMERS; FLUORESCENCE; SEMICONDUCTOR DEVICES; SYNTHESIS (CHEMICAL); TOLUENE; ULTRAVIOLET SPECTROSCOPY;

CONVERGENT SYNTHESIS; INTERNAL CONVERSION RATES; OPTICAL BAND GAPS; PHENYL CORED THIOPHENE DENDRIMERS;

PHENOLS;

EID: 27844456454     PISSN: 09599428     EISSN: 13645501     Source Type: Journal    
DOI: 10.1039/b508683c     Document Type: Article

References (71)

1. (a) O. A. Matthews, A. N. Shipway and J. F. Stoddart, Prog. Polym. Sci., 1998, 23, 1, 1-56;
2. (b) A. Adronov and J. M. J. Fréchet, Chem. Commun., 2000, 1701-1710.
3. (a) C. Devadoss, P. Bharathi and J. S. Moore, J. Am. Chem. Soc., 1996, 118, 9635-9644;
4. (b) Q.-S. Hu, V. Pugh, M. Sabat and L. Pu, J. Org. Chem., 1999, 64, 7528-7536;
5. (c) Z. Peng, Y. Pan, B. Xu and J. Zhang, J. Am. Chem. Soc., 2000, 122, 6619-6623.
6. A. J. Berresheim, M. Müller and K. Müllen, Chem. Rev., 1999, 99, 1747-1785.
7. (a) M. Halim, J. N. G. Pillow, I. D. W. Samuel and P. L. Burn, Synth. Met., 1999, 102, 922-923;
8. (b) J. N. G. Pillow, M. Halim, J. M. Lupton, P. L. Burn and I. D. W. Samuel, Macromolecules, 1999, 32, 19, 5985-5993.
9. (a) C. Xia, X. Fan, J. Locklin and R. C. Advincula, Org. Lett., 2002, 4, 12, 2067-2070;
10. (b) C. Xia, X. Fan, J. Locklin, R. C. Advincula, A. Gies and W. Nonidez, J. Am. Chem. Soc., 2004, 126, 8735-8743.
11. (a) R. D. McCullough, Adv. Mater., 1998, 10, 2, 93-116;
12. (b) D. Fichou, Handbook of Oligo- and Polythiophenes, Wiley-VCH, New York, 1998.
13. (a) D. Braun, G. Gustafsson, D. McBranch and A. J. Heeger, J. Appl. Phys., 1992, 72, 2, 564-568;
14. (b) F. Geiger, M. Stoldt, H. Schweizer, P. Bauerle and E. Umbach, Adv. Mater., 1993, 5, 12, 922-925;
15. (c) G. Horowitz, P. Delannoy, H. Bouchriha, F. Deloffre, J. L. Fave, F. Garnier, R. Hajlaoui, M. Heyman, F. Kouki, P. Valat, V. Wintgens and A. Yassar, Adv. Mater., 1994, 6, 10, 752-755;
16. (d) P. Dyreklev, M. Berggren, O. Inganas, M. R. Andersson, O. Wennerstrom and T. Hjertberg, Adv. Mater., 1995, 7, 1, 43-45;
17. (e) R. N. Marks, F. Biscarini, R. Zamboni and C. Taliani, Europhys. Lett., 1995, 32, 6, 523-528;
18. (f) P. Barta, W. R. Salaneck, M. Zagorska, A. Pron and S. Niziol, Adv. Mater. Opt. Electron., 1996, 6, 5-6, 406-408;
19. (g) C. Vaterlein, H. Neureiter, W. Gebauer, B. Ziegler, M. Sokolowski, P. Bauerle and E. Umbach, J. Appl. Phys., 1997, 82, 6, 3003-3013;
20. (h) M. Granström, Polym. Adv. Technol., 1997, 8, 7, 424-430;
21. (i) U. Mitschke and P. Bäuerle, J. Chem. Soc., Perkin Trans. 1, 2001, 740-753;
22. (j) G. Gigli, M. Anni, M. Theander, R. Cingolani, G. Barbarella, L. Favaretto and O. Inganäs, Synth. Met., 2001, 119, 581-582.
23. (a) F. Garnier, A. Yasser, R. Hajlaoui, G. Horowitz, F. Deloffre, B. Servet, S. Ries and P. Alnot, J. Am. Chem. Soc., 1993, 115, 19, 8716-8721;
24. (b) A. Dodabalapur, L. Torsi and H. E. Katz, Science, 1995, 268, 270-271;
25. (c) A. J. Lovinger and L. J. Rothberg, J. Mater. Res., 1996, 11, 6, 1581-1592;
26. (d) Y. Wei, Y. Yang and J. M. Yeh, Chem. Mater., 1996, 8, 11, 2659-2666;
27. (e) A. R. Brown, C. P. Jarrett, D. M. deLeeuw and M. Matters, Synth. Met., 1997, 88, 1, 37-55;
28. (f) H. E. Katz, Z. N. Bao and S. L. Gilat, Acc. Chem. Res., 2001, 34, 5, 359-369;
29. (g) X. M. Hong, H. E. Katz, A. J. Lovinger, B. C. Wang and K. Raghavachari, Chem. Mater., 2001, 13, 12, 4686-4691;
30. (h) S. A. Ponomarenko, S. Kirchmeyer, A. Elschner, B. - H. Huisman, A. Karbach and D. Drechsler, Adv. Funct. Mater., 2003, 13, 8, 591-596.
31. (a) N. Noma, T. Tsuzuki and Y. Shirota, Adv. Mater., 1995, 7, 7, 647-648;
32. (b) M. Granström, K. Petritsch, A. C. Arias, A. Lux, M. R. Andersson and R. H. Friend, Nature, 1998, 395, 257-260;
33. (c) L. Chen, L. S. Roman, D. M. Johansson, M. Svensson, M. R. Andersson, R. A. J. Janssen and O. Inganäs, Adv. Mater., 2000, 12, 15, 1110-1114;
34. (d) T. Fromherz, F. Padinger, D. Gebeyehu, C. Brabec, J. C. Hummelen and N. S. Sariciftci, Sol. Energy Mater. Sol Cells, 2000, 63, 1, 61-68;
35. (e) J. J. Dittmer, E. A. Marseglia and R. H. Friend, Adv. Mater., 2000, 12, 17, 1270-1274;
36. (f) W. Feng, A. Fujii, S. Lee, H. Wu and K. Yoshino, J. Appl. Phys., 2000, 88, 12, 7120-7123;
37. (g) S. E. Shaheen, D. Vangeneugden, R. Kiebooms, D. Vanderzande, T. Fromherz, F. Padinger, C. J. Brabec and N. S. Sariciftci, Synth. Met., 2001, 121, 1-3, 1583-1584;
38. (h) C. J. Brabec, N. S. Sariciftci and J. C. Hummelen, Adv. Funct. Mater., 2001, 11, 1, 15-26;
39. (i) L. Tan, M. D. Curtis and A. H. Francis, Macromolecules, 2002, 35, 12, 4628-4635;
40. (j) F. Padinger, R. S. Rittberger and S. Sariciftci, Adv. Funct. Mater., 2003, 13, 1, 85-88;
41. (k) D. Chirvase, Z. Chiguvare, M. Knipper, J. Parisi, V. Dyakonov and J. C. Hummelen, Synth. Met., 2003, 138, 299-304.
42. (a) J. Roncali, Chem. Rev., 1997, 97, 173-205;
43. (b) H. Saadeh, T. Goodson and L. P. Yu, Macromolecules, 1997, 30, 16, 4608-4612;
44. (c) W. Huang, H. Meng, W. L. Yu, J. Gao and A. J. Heeger, Adv. Mater., 1998, 10, 8, 593-596;
45. (d) A. Greiner, Polym. Adv. Technol., 1998, 9, 7, 371-389;
46. (e) U. Mitschke and P. Bäuerle, J. Mater. Chem., 2000, 10, 1471-1507.
47. (a) R. D. McCullough and R. D. Lowe, J. Chem. Soc., Chem. Commun., 1992, 70-72;
48. (b) R. D. McCullough, R. D. Lowe, M. Jayaraman and D. L. Anderson, J. Org. Chem., 1993, 58, 904-912;
49. (c) T.-A. Chen, X. Wu and R. D. Rieke, J. Am. Chem. Soc., 1995, 117, 233-244.
50. (a) J. Nakayama and J.-S. Lin, Tetrahedron Lett., 1997, 38, 34, 6043-6046;
51. (b) R.-M. Sebastian, A.-M. Caminade, J.-P. Majoral, E. Levillian, L. Huchet and J. Roncali, Chem. Commun., 2000, 507-508;
52. (c) J. Alvarez, L. Sun and R. M. Crooks, Chem. Mater., 2002, 14, 3995-4001;
53. (d) M.-H. Xu and L. Pu, Tetrahedron Lett., 2002, 43, 6347-6350;
54. (e) M. J. Frampton, E. B. Namdas, S.-C. Lo, P. L. Burn and I. D. W. Samuel, J. Mater. Chem., 2004, 14, 2881-2888;
55. (f) J. P. J. Markham, E. B. Namdas, T. D. Anthopoulos, I. D. W. Samuel, G. J. Richards and P. L. Burn, Appl. Phys. Lett., 2004, 85, 9, 1463-1465.
56. C. V. Pham, A. Burkhardt, R. Shabana, D. D. Cunningham, H. B. Mark and H. Zimmer, Phosphorus Sulfur, 1989, 46, 153-168.
57. J. B. Bicks, Photophysics of Aromatic Molecules, John Wiley & Sons, Chichester, 1970, pp. 113-118.
58. A. Breeze, D. Ginley and B. Gregg, Proc. NCPV Solar Program Review Meeting 2003, 2003, 690-692.
59. Y. Li, G. Vamvounis and S. Holdcroft, Macromolecules, 2002, 35, 6900-6906.
60. M. Theander, O. Inganäs, W. Mammo, T. Olinga, M. Svensson and M. R. Andersson, J. Phys. Chem. B, 1999, 103, 37, 7771-7780.
61. S. Hoger, J. Spickermann, D. L. Morrison, P. Dziezok and H. J. Rader, Macromolecules, 1997, 30, 3110-3111.
62. L. Jinsong, R. S. Loewe and R. D. McCullough, Macromolecules, 1999, 32, 5777-5785.
63. B. A. Gregg, MRS Bull., 2005, 30, 1, 20-22.
64. I. H. Campbell, T. H. Hagler, D. L. Smith and J. P. Ferraris, Phys. Rev. Lett., 1996, 76, 11, 1900-1903.
65. D. Phillips and D. V. O'Connor, Time-Correlated Single-Photon Counting, Academic Press, London, 1984.
66. T. Gennett, D. F. Milner and M. J. Weaver, J. Phys. Chem., 1985, 89, 13, 2787-2794.
67. N. G. Connelly and W. E. Geiger, Chem. Rev., 1996, 96, 877-810.
68. A. J. Bard and L. R. Faulkner, Electrochemical Methods: Fundamentals and Applications, John Wiley & Sons, Chichester, 1980.
69. J. T. Pinhey and E. G. Roche, J. Chem. Soc., Perkin Trans. 1, 1988, 8, 2415-2421.
70. A. Pelter, I. Jenkins and D. E. Jones, Tetrahedron, 1997, 53, 30, 10357-10400.
71. F. Cherioux and L. Guyard, Adv. Funct. Mater., 2001, 11, 4, 305-309.