Synthesis and characterization of soluble low-bandgap oligothiophene-[all]- S,S-dioxides-based conjugated oligomers and polymers

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 49, Issue 9, 2011, Pages 1933-1941

  Amir, Elizabeth ^a   Sivanandan, Kulandaivelu ^a   Cochran, Justin E ^a   Cowart, John J ^a   Ku, Sung Yu ^a   Seo, Jung Hwa ^b   Chabinyc, Michael L ^a,b   Hawker, Craig J ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b University of California   (United States)

Author keywords

conjugated polymers; crystal structures; oligomers; synthesis; UV vis spectroscopy

Indexed keywords

CRYSTAL STRUCTURE; DYES; ENERGY GAP; MOLECULAR ORBITALS; OLIGOMERS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL); ULTRAVIOLET VISIBLE SPECTROSCOPY;

CONJUGATED OLIGOMER; ELECTRON-ACCEPTING; FRONTIER ORBITALS; HIGHEST OCCUPIED MOLECULAR ORBITAL; LOWEST UNOCCUPIED MOLECULAR ORBITAL; MICROWAVE ASSISTED; SYNTHESIS AND CHARACTERIZATIONS; UV-VIS SPECTROSCOPY;

CONJUGATED POLYMERS;

EID: 79953049889     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.24641     Document Type: Article

References (49)

1. (a), Osaka, I.,;, Zhang, R.,;, Sauvé, G.,;, Smilgies, D.-M.,;, Kowalewski, T.,;, McCullough, R. D., J Am Chem Soc, 2009, 131, 2521-2529
2. (b), McCullough, I.,;, Heeney, M.,;, Bailey, C.,;, Genevicius, K.,;, Macdonald, I.,;, Shkunov, M.,;, Sparrowe, D.,;, Tierney, S.,;, Wagner, R.,;, Zhang, W.,;, Chabinyc, M. L.,;, Kline, R. J.,;, McGehee, M. D.,;, Toney, M. F., Nat Mater 2006, 5, 328-333
3. (c), Anthony, J. E., Chem Rev 2006, 106, 5028-5048
4. (d), Ong, B. S.,;, Wu, Y.,;, Liu, P.,;, Gardner, S., J Am Chem Soc 2004, 126, 3378-3379
5. (e), Treat, N. D.,;, Brady, M. A.,;, Smith, G.,;, Toney, M. F.,;, Kramer, E. J.,;, Hawker, C. J.,;, Chabinyc, M. L., Adv Energy Mater 2011, 1, 82-89
6. (f), Treat, N. D.,;, Campos, L. M.,;, Dimitriou, M. D.,;, Ma, B.,;, Chabinyc, M. L.,;, Hawker, C. J., Adv Mater 2010, 22, 4982-4986.
7. (a), Wang, C.,;, Kim, F. S.,;, Ren, G.,;, Xu, Y.,;, Pang, Y.,;, Jenekhe, S. A.,;, Jia, L. J., Polym Sci Part A: Polym Chem 2010, 48, 4681-4690
8. (b), Nedeltchev, A. K.,;, Han, H.,;, Bhowmik, P. K., J Polym Sci Part A: Polym Chem 2010, 48, 4611-4620
9. (c), Rusu, R. D.,;, Damaceanu, M. D.,;, Marin, L.,;, Bruma, M., J Polym Sci Part A: Polym Chem 2010, 48, 4230-4242
10. (d), Qu, H.,;, Luo, J.,;, Zhang, X.,;, Chi, C., J Polym Sci Part A: Polym Chem 2010, 48, 186-194
11. (e), Peng, Q.,;, Xu, J.,;, Zheng, W., J Polym Sci Part A: Polym Chem 2010, 48, 3399-3408.
12. (a), Facchetti, A.,;, Yoon, M.-H.,;, Stern, C. L.,;, Hutchison, G. R.,;, Ratner, M. A.,;, Marks, T. J., J Am Chem Soc 2004, 126, 13480-13501
13. (b), Ie, Y.,;, Nitani, M.,;, Ishikawa, M.,;, Nakayama, K.,;, Tada, H.,;, Kaneda, T.,;, Aso, Y., Org Lett 2007, 9, 2115-2118.
14. Yoon, M.-H.,;, DiBenedetto, S. A.,;, Facchetti, A.,;, Marks, T. J., J Am Chem Soc 2005, 127, 1348-1349.
15. Ie, Y.,;, Umemoto, Y.,;, Okabe, M.,;, Kusunoki, T.,;, Nakayama, K.,;, Pu, Y.-J.,;, Kido, J.,;, Tada, H.,;, Aso, Y., Org Lett 2008, 10, 833-836.
16. (a), Rozen, S.,;, Bareket, Y., J Chem Soc Chem Commun 1994, 17, 1959-1960
17. (b), Rozen, S.,;, Bareket, Y., J Org Chem 1997, 62, 1457-1462.
18. Miyahara, Y.,;, Inazu, T., Tetrahedron Lett 1990, 31, 5955-5958.
19. (a), Oliva, M. M.,;, Casado, J.,;, Lõpez Navarrete, J. T.,;, Patchkovskii, S.,;, Goodson, T., III,;, Harpham, M. R.,;, Seixas de Melo, J. S.,;, Amir, E.,;, Rozen, S., J Am Chem Soc 2010, 132, 6231-6242
20. (b), Zhang, C.,;, Nguyen, T. H.,;, Sun, J.,;, Li, R.,;, Black, S.,;, Bonner, C. E.,;, Sun, S.-S., Macromolecules 2009, 42, 663-670
21. (c), King, S. M.,;, Perepichka, I. I.,;, Perepichka, I. F.,;, Dias, F. B.,;, Bryce, M. R.,;, Monkman, A. P., Adv Funct Mater 2009, 19, 586-591
22. (d), Huang, T.-H.,;, Lin, J. T.,;, Chen, L.-Y.,;, Lin, Y.-T.,;, Wu, C.-C., Adv Mater 2006, 18, 602-606
23. (e), Perepichka, I. I.,;, Perepichka, I. F.,;, Bryce, M. R.,;, PÃ¥lsson, L.-O., Chem Commun 2005, 27, 3397-3399
24. (f), Beaupré, S.,;, Leclerc, M., Adv Funct Mater 2002, 12, 192-196
25. (g), Yamamoto, T.,;, Nurulla, I.,;, Hayashi, H.,;, Koinuma, H., Synth Met 1999, 107, 137-141.
26. (a), Barbarella, G.,;, Pudova, O.,;, Arbizzani, C.,;, Mastragostino, M.,;, Bongini, A., J Org Chem 1998, 63, 1742-1745
27. (b), Barbarella, G.,;, Favaretto, L.,;, Zambianchi, M.,;, Pudova, O.,;, Arbizzani, C.,;, Bongini, A.,;, Mastragostino, M., Adv Mater 1998, 10, 551-554.
28. (a), Melucci, M.,;, FrÃ̈re, P.,;, Allain, M.,;, Levillain, E.,;, Barbarella, G.,;, Roncali, J., Tetrahedron 2007, 63, 9774-9783
29. (b), Camaioni, N.,;, Ridolfi, G.,;, Fattori, V.,;, Favaretto, L.,;, Barbarella, G., Appl Phys Lett 2004, 84, 1901-1903
30. (c), Barbarella, G.,;, Favaretto, L.,;, Sotgiu, G.,;, Zambianchi, M.,;, Fattori, V.,;, Cocchi, M.,;, Cacialli, F.,;, Gigli, G.,;, Cingolani, R., Adv Mater 1999, 11, 1375-1379.
31. Amir, E.,;, Rozen, S., Angew Chem Int Ed 2005, 44, 7374-7378.
32. Takahashi, M.,;, Masui, K.,;, Sekiguchi, H.,;, Kobayashi, N.,;, Mori, A.,;, Funahashi, M.,;, Tamaoki, N., J Am Chem Soc 2006, 128, 10930-10933.
33. 3CN from either commercially prediluted or pure (95%) fluorine can be found in:, Dayan, S.,;, Bareket, Y.,;, Rozen, S.,; Tetrahedron 1999, 55, 3657-3664.
34. Janzen, D. E.,;, Burand, M. W.,;, Ewbank, P. C.,;, Pappenfus, T. M.,;, Higuchi, H.,;, da Silva Filho, D. A.,;, Young, V. G.,;, Brédas, J.-L.,;, Mann, K. R., J Am Chem Soc 2004, 126, 15295-15308.
35. Raimundo, J.-M.,;, Blanchard, P.,;, Gallego-Planas, N.,;, Mercier, N.,;, Ledoux-Rak, I.,;, Hierle, R.,;, Roncali, J., J Org Chem 2002, 67, 205-218.
36. Ruiz Delgado, M. C.,;, Pigg, K. R.,;, da Silva Filho, D. A.,;, Gruhn, N. E.,;, Sakamoto, Y.,;, Suzuki, T.,;, Malavé Osuna, R.,;, Casado, J.,;, Hernández, V.,;, Lõpez Navarrete, J. T.,;, Martinelli, N. G.,;, Cornil, J.,;, Sánchez-Carrera, R. S.,;, Coropceanu, V.,;, Brédas, J.-L., J Am Chem Soc 2009, 131, 1502-1512.
37. Seitz, D. E.,;, Lee, S.-H.,;, Hanson, R. N.,;, Bottaro, J. C., Synth Commun 1983, 13, 121-128.
38. Tierney, S.,;, Heeney, M.,;, McCulloch, I., Synth Met 2005, 148, 195-198.
39. Seo, J. H.,;, Yang, R.,;, Brzezinski, J. Z.,;, Walker, B.,;, Bazan, G. C.,;, Nguyen T. Q., Adv Mater 2009, 21, 1006-1011.
40. Fahlman, M.,;, Crispin, A.,;, Crispin, X.,;, Henze, S. K. M.,;, de Jong, M. P.,;, Osikowicz, W.,;, Tengstedt, C.,;, Salaneck, W. R., J Phys: Condens Matter 2007, 19, 183202 (20 pp).
41. (a), Sariciftci, N. S.,;, Smilowitz, L.,;, Heeger, A. J.,;, Wudl, F., Science 1992, 258, 1474-1476
42. (b), Wessendorf, F.,;, Grimm, B.,;, Guldi, D.M.,;, Hirsch, A., J Am Chem Soc 2010, 132, 10786-10795
43. (c), Hsieh, C.,;, Cheng, Y.,;, Li, P.,;, Chen, C.,;, Dubosc, M.,;, Hsu, C., J Am Chem Soc 2010, 132, 4887-4893
44. (d), Hawker, C. J.,;, Saville, P. M.,;, White, J. W., J Org Chem 1994, 59, 3503-3505
45. (e), Saville, P. M.,;, Reynolds, P. A.,;, White, J. W.,;, Hawker, C. J.,;, Frechet, J. M. J.,;, Wooley, K. L.,;, Penfold, J.,;, Webster, J. R. P., J Phys Chem 1995, 99, 8283-8289.
46. Wan, M.,;, Wu, W.,;, Sang, G.,;, Zou, Y.,;, Liu, Y.,;, Li, Y., J Polym Sci Part A: Polym Chem 2009, 47, 4028-4036.
47. Gallazzi, M. C.,;, Castellani, L.,;, Zerbi, G.,;, Sozzani, P., Synth Met 1991, 41, 495-498.
48. Gallazzi, M. C.,;, Bertarelli, C.,;, Montoneri, E., Synth Met 2002, 128, 91-95.
49. Jones, C. L.,;, Higgins, S. J., J Mater Chem 1999, 9, 865-874.