Poly(2,3-dihexylthieno[3,4-b]pyrazine) via GRIM polymerization: Simple preparation of a solution processable, low-band-gap conjugated polymer

Macromolecules

Volumn 41, Issue 13, 2008, Pages 4576-4578

  Wen, Li ^a   Duck, Benjamin C ^b   Dastoor, Paul C ^b   Rasmussen, Seth C ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NEWCASTLE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BAND GAPS; PYRAZINE (A);

CHEMICAL REACTIONS; MONOMERS; POLYMERIZATION; POLYMERS;

CONJUGATED POLYMERS;

EID: 47949097563     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma801057s     Document Type: Article

References (45)

1. (a) Semiconducting Polymers: Chemistry, Physics and Engineering; Hadziioannou, G., van Hutten, P. F., Eds.; Wiley-VCH: Weinheim, 2000.
2. (b) Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, 1999.
3. (c) Roneali, J. Chem. Rev. 1992, 92, 711.
4. (a) Roneali, J. Chem. Rev. 1997, 97, 173.
5. (b) Rasmussen, S. C.; Pomerantz, M. In Handbook of Conducting Polymers, 3rd ed.; Skotheim, T. A., Reynolds, J. R., Eds.; CRC Press: Boca Raton, FL, 2007; Vol. 1, Chapter 12.
6. Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382.
7. Nayak, K.; Marynick, D. S. Macromolecules 1990, 23, 2237.
8. (a) Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J. J.; Pomerantz, W. J. J. Chem. Soc., Chem. Commun. 1992, 1672.
9. (b) Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J. J.; Pomerantz, W. J. Synth. Met. 1993, 55, 960.
10. (a) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Synth. Met. 1995, 69, 593.
11. (b) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Macromolecules 1995, 28, 2922.
12. (a) van Asselt, R.; Hoogmartens, I.; Vanderzande, D.; Gelan, J.; Froehling, P. E.; Aussems, M.; Aagaard, O.; Schellekens, R. Synth. Met. 1995, 74, 65.
13. (b) Huskic, M.; Vanderzande, D.; Gelan, J. Synth. Met. 1999, 99, 143.
14. Hagan, A. J.; Moratti, S. C.; Sage, I. C. Synth. Met. 2001, 119, 147.
15. Kenning, D. D.; Rasmussen, S. C. Macromolecules 2003, 36, 6298.
16. (a) Kitamura, C.; Tanaka, S.; Yamashita, Y. J. Chem. Soc., Chem. Commun. 1994, 1585.
17. (b) Kitamura, C.; Tanaka, S.; Yamashita, Y. Chem. Mater. 1996, 8, 570.
18. (c) Sonmez, G.; Shen, C. K. F.; Rubin, Y.; Wudl, F. Angew. Chem., Int. Ed. 2004, 43, 1498.
19. (d) Sonmez, G.; Sonmez, H. B.; Shen, C. K. F.; Jost, R. W.; Rubin, Y.; Wudl, F. Macromolecules 2005, 38, 669.
20. (e) Sonmez, G.; Sonmez, H. B.; Shen, C. K. F.; Wudl, F. Adv. Mater. 2004, 16, 1905.
21. (f) Sonmez, G.; Shen, C. K. F.; Rubin, Y.; Wudl, F. Adv. Mater. 2005, 17, 897.
22. (g) Berlin, A.; Zotti, G.; Zecchin, S.; Schiavon, G.; Vercelli, B.; Zanelli, A. Chem. Mater. 2004, 16, 3667.
23. (h) Wienk, M. M.; Turbiez, M. G. R.; Struijk, M. P.; Fonrodona, M.; Janssen, R. A. J. Appl. Phys. Lett. 2006, 88, 153511.
24. (a) Akoudad, S.; Roneali, J. Chem. Commun. 1998, 2081.
25. (b) Perepichka, I. F.; Levillain, E.; Roneali, J, J. Mater. Chem. 2004, 14, 1679.
26. (a) Bundgaard, E.; Krebs, F. C. Solar Energy Mater. Solar Cells 2007, 91, 954.
27. (b) Petersen, M. H.; Hagemann, O.; Nielsen, K. T.; Jørgensen, M.; Krebs, F. C. Solar Energy Mater. Solar Cells 2007, 91, 996.
28. (c) Zhang, F.; Perzon, E.; Wang, X.; Mammo, W.; Andersson, M. R.; Inganäs, O. Adv. Funct. Mater. 2005, 15, 745.
29. (a) Loewe, R. S.; Khersonsky, S. M.; McCullough, R. D. Adv. Mater. 1999, 11, 250.
30. (b) Loewe, R. S.; Ewbank, P. C.; Liu, J.; Zhai, L.; McCullough, R. D. Macromolecules 2001, 34, 4324.
31. (c) Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D. Macromolecules 2005, 38, 8649.
32. (d) Jeffreies-El, M.; McCullough, R. D. In Handbook of Conducting Polymers, 3rd ed.; Skotheim, T. A., Reynolds, J. R., Eds.; CRC Press: Boca Raton, FL, 2007; Vol. 1, Chapter 9.
33. Sheina, E. E.; Khersonsky, S. M.; Jones, E. G.; McCullough, R. D. Chem. Mater. 2005, 17, 3317.
34. (a) Wen, L.; Rasmussen, S. C. J. Chem. Crystallogr. 2007, 37, 387.
35. (b) Kenning, D. D.; Mitchell, K. A.; Calhoun, T. R.; Funfar, M. R.; Sattler, D. J.; Rasmussen, S. C. J. Org. Chem. 2002, 67, 9073.
36. Dastoor, P. C.; McNeill, C. R.; Frohne, H.; Foster, C. J.; Dean, B.; Fell, C. J.; Belcher, W. J.; Campbell, W. M.; Officer, D. L.; Blake, I. M.; Thordarson, P.; Crossley, M. J.; Hush, N. S.; Reimers, J. R. J. Phys. Chem. C 2007, 111, 15415.
37. Thompson, B. C.; Kim, Y.-G.; McCarley, T. D.; Reynolds, J. R. J. Am. Chem. Soc. 2006, 128, 12714.
38. (a) Dhanabalan, A.; van Duren, J. K. J.; van Hal, P. A.; van Dongen, J. L. J.; Janssen, R. A. J. Adv. Funct. Mater. 2001, 11, 255.
39. (b) Brabec, C. J.; Winder, C.; Sariciftci, N. S.; Hummelen, J. C.; Dhanabalan, A.; van Hal, P. A.; Janssen, R. A. J. Adv. Funct. Mater. 2002, 12, 709.
40. (a) Wang, X.; Perzon, E.; Delgado, J. L.; de la Cruz, P.; Zhang, F.; Langa, F.; Andersson, M.; Inganäs, O. Appl. Phys. Lett. 2004, 85, 5081.
41. (b) Wang, X.; Perzon, E.; Oswald, F.; Langa, F.; Admassie, S.; Andersson, M. R.; Inganäs, O. Adv. Funct. Mater. 2005, 15, 1665.
42. (c) Wang, X.; Perzon, E.; Mammo, W.; Oswald, F.; Admassie, S.; Persson, N.-K.; Langa, F.; Andersson, M. R.; Inganäs, O. Thin Solid Films 2006, 511-12, 576.
43. Xia, Y.; Wang, L.; Deng, X.; Li, D.; Zhu, X.; Cao, Y. Appl. Phys. Lett. 2006, 89, 081106.
44. Goris, L.; Loi, M. A.; Cravino, A.; Neugebauer, H.; Sariciftci, N. S.; Polea, I.; Lutsen, L.; Andries, E.; Manca, J.; De Schepper, L.; Vanderzande, D. Synth. Met. 2003, 138, 249.
45. Perzon, E.; Zhang, F.; Andersson, M.; Mammo, W.; Inganäs, O.; Andersson, M. R. Adv. Mater. 2007, 19, 3308.