Pure Appl. Chem., 2008, Vol. 80, No. 3, pp. 589-597
http://dx.doi.org/10.1351/pac200880030589
Perfluoroalkyl-annelated conjugated systems toward n-type organic semiconductors
References
- 1. For a recent review on organic electronics, see the special issue of Chemistry of Materials: Chem. Mater. 16, 4381-4846 (2004). (http://dx.doi.org/10.1021/cm041000r)
- 2. (a). I. McCulloch, M. Heeney, C. Bailey, K. Genevicius, I. Macdonald, M. Shkunov, D. Sparrowe, S. Tierney, R. Wagner, W. Zhang, M. L. Chabinyc, R. J. Kline, M. D. McGehee, M. F. Toney. Nat. Mater. 5, 328 (2006); (http://dx.doi.org/10.1038/nmat1612)
- 2. (b). M. Muccini. Nat. Mater. 5, 605 (2006); (http://dx.doi.org/10.1038/nmat1699)
- 2. (c). K. Takimia, Y. Kunugi, T.Otsubo. Chem. Lett. 36, 573 (2007).
- 3. (a). C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J.-L. Bredas, P. C. Ewbank, K. R. Mann. Chem. Mater. 16, 4436 (2004); (http://dx.doi.org/10.1021/cm049391x)
- 3. (b). A. Facchetti, M.-H. Yoon, T. J. Marks. Adv. Mater. 17, 1705 (2005). (http://dx.doi.org/10.1002/adma.200500517)
- 4. (a). A. Facchetti, Y. Deng, A. Wang, Y. Koide, H. Sirringhaus, T. J. Marks, R. H. Friend. Angew. Chem., Int. Ed. 39, 4547 (2000); (http://dx.doi.org/10.1002/1521-3773(20001215)39:24<4547::AID-ANIE4547>3.0.CO;2-J)
- 4. (b). A. Facchetti, M. Mushrush, H. E. Katz, T. J. Marks. Adv. Mater. 15, 33 (2003); (http://dx.doi.org/10.1002/adma.200390003)
- 4. (c). L. Li, K. E. Counts, S. Kurosawa, A. S. Teja, D. M. Collard. Adv. Mater. 16, 180 (2004); (http://dx.doi.org/10.1002/adma.200305333)
- 4. (d). G. R. Dholakia, M. Meyyappan, A. Facchetti, T. J. Marks. Nano Lett. 6, 2447 (2006). (http://dx.doi.org/10.1021/nl061566+)
- 5. (a). A. Facchetti, M.-H. Yoon, C. L. Stern, G. R. Hutchison, M. A. Ratner, T. J. Marks. J. Am. Chem. Soc. 126, 13480 (2004); (http://dx.doi.org/10.1021/ja048988a)
- 5. (b). A. Facchetti, M. Mushrush, M.-H. Yoon, G. R. Hutchison, M.A. Ratner, T. J. Marks. J. Am. Chem. Soc. 126, 13859 (2004). (http://dx.doi.org/10.1021/ja0489846)
- 6. (a). S. Ando, J. Nishida, E. Fujiwara, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita. Chem. Mater. 17, 1261 (2005); (http://dx.doi.org/10.1021/cm0478632)
- 6. (b). S. Ando, J. Nishida, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita. J. Am. Chem. Soc. 127, 5336 (2005); (http://dx.doi.org/10.1021/ja042219+)
- 6. (c). S. Ando, R. Murakami, J. Nishida, H. Tada, Y. Inoue, S. Tokito, Y.Yamashita. J. Am. Chem. Soc. 127, 14996 (2005). (http://dx.doi.org/10.1021/ja055686f)
- 7. T. Izumi, S. Kobashi, K. Takimiya, Y. Aso, T. Otsubo. J. Am. Chem. Soc. 125, 5286 (2003). (http://dx.doi.org/10.1021/ja034333i)
- 8. All calculations were conducted using Gaussian 03 program. The geometry was optimized with the restricted Becke hybrid (B3LYP) at the 6-31G(d,p) level.
- 9. Y. Ie, Y. Umemoto, T. Kaneda, Y. Aso. Org. Lett. 8, 5381 (2006). (http://dx.doi.org/10.1021/ol062238j)
- 10. Y. Ie, Y. Umemoto, Y. Aso. Unpublished results.
- 11. Crystal data for 5: C31H12F12O2S3, M = 396.38, triclinic, space group P-1(#2), a = 10.6341(7), b= 10.7730(6), c = 15.0458(8) A, a = 70.3968(15)deg, b = 71.0859(19)deg, g = 64.2458(18)deg, V= 1429.78(14) A3, Z = 2, Dcalc = 1.720 gcm-3, F(000) = 740.00, m = 3.694 cm-1 (MoKa; l = 0.71075 A), 29507 reflections measured, 8692 unique, R = 0.0634 for I > 2s(I), wR = 0.1457 for all data.
- 12. Y. Ie, M. Nitani, M. Ishikawa, K.-i. Nakayama, H. Tada, T. Kaneda, Y. Aso. Org. Lett. 9, 2115 (2007). (http://dx.doi.org/10.1021/ol070584a)
- 13. T. Hadizad, J. Zhang, Z. Y. Wang, T. C. Gorjanc, C. Py. Org. Lett. 7, 795 (2005). (http://dx.doi.org/10.1021/ol0476570)
- 14. (a). J. P. M. Serbena, I. A. Hummelgen, T. Hadizad, Z. Y. Wang. Small 2, 372 (2006); (http://dx.doi.org/10.1002/smll.200500305)
- 14. (b). C. Py, T. C. Gorjanc, T. Hadizad, J. Zhang, Z. Y. Wang, J. Vac. Sci. Technol. A 24, 654 (2006); (http://dx.doi.org/10.1116/1.2180265)
- 14. (c). T.Hadizad, J. Zhang, D. Yan, Z. Y. Wang, J. P. M. Serbena, M. S. Meruvia, I. A. Hummelgen. J. Mater. Sci. Mater. Electron. 18, 903 (2007). (http://dx.doi.org/10.1007/s10854-006-9067-6)
- 15. J. P. Amara, T. M. Swager. Macromolecules 39, 5753 (2006). (http://dx.doi.org/10.1021/ma0608572)
- 16. Y. Ie, M. Nitani, Y. Aso. Chem. Lett. 36, 1326 (2007). (http://dx.doi.org/10.1246/cl.2007.1326)