Table of Contents
Journal of Crystallography
Volume 2014, Article ID 257249, 5 pages
http://dx.doi.org/10.1155/2014/257249
Research Article

Molecular Structure and Crystal Packing of n-Type Semiconducting Material 3′,3′-(1,4-Phenylene)bis{2′-(4′′-trifluoromethyl)phenyl}acrylonitrile

1Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu 804-8550, Japan
2Department of Computer Science and Electronics, Kyushu Institute of Technology, 680-4 Kawazu, Iizuka, Fukuoka 820-8502, Japan
3Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, 2-4 Hibikino, Wakamatsu-ku, Kitakyushu 808-0196, Japan

Received 28 April 2014; Accepted 13 June 2014; Published 19 August 2014

Academic Editor: Mehmet Akkurt

Copyright © 2014 Tetsuji Moriguchi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. H. E. Katz, Z. Bao, and S. L. Gilat, “Synthetic chemistry for ultrapure, processable, and high-mobility organic transistor semiconductors,” Accounts of Chemical Research, vol. 34, no. 5, pp. 359–369, 2001. View at Publisher · View at Google Scholar
  2. C. D. Dimitrakopoulos and P. R. L. Malenfant, “Organic thin film transistors for large area electronics,” Advanced Materials, vol. 14, no. 2, pp. 99–117, 2002. View at Google Scholar
  3. S. Nagamatsu, K. Kaneto, R. Azumi, M. Matsumoto, Y. Yoshida, and K. Yase, “A steady operation of n-type organic thin-film transistors with cyano-substituted distyrylbenzene derivative,” The Journal of Physical Chemistry B, vol. 109, no. 19, pp. 934–937, 2005. View at Google Scholar
  4. G. Gu, M. G. Kane, J. E. Doty, and A. H. Firester, “Electron traps and hysteresis in pentacene-based organic thin-film transistors,” Applied Physics Letters, vol. 87, no. 24, Article ID 243512, 3 pages, 2005. View at Publisher · View at Google Scholar · View at Scopus
  5. S. C. Lim, S. H. Kim, G. H. Kim et al., “High-gain and low-hysteresis properties of organic inverters with an UV-photo patternable gate dielectrics,” Thin Solid Films, vol. 516, no. 12, pp. 4330–4333, 2008. View at Publisher · View at Google Scholar · View at Scopus
  6. B. A. Jones, M. J. Ahrens, M. Yoon, A. Facchetti, T. J. Marks, and M. R. Wasielewski, “High-mobility air-stable n-type semiconductors with processing versatility: dicyanoperylene-3,4:9,10-bis(dicarboximides),” Angewandte Chemie, vol. 43, no. 46, pp. 6363–6366, 2004. View at Publisher · View at Google Scholar · View at Scopus
  7. B. A. Jones, A. Facchetti, M. R. Wasielewski, and T. J. Marks, “Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport,” Journal of the American Chemical Society, vol. 129, no. 49, pp. 15259–15278, 2007. View at Publisher · View at Google Scholar · View at Scopus
  8. T. Yasuda, M. Saito, H. Nakamura, and T. Tsutsui, “Control of p- and n-type carriers by end-group substitution in oligo-p-phenylenevinylene-based organic field-effect transistors,” Applied Physics Letters, vol. 89, Article ID 182108, 2006. View at Publisher · View at Google Scholar
  9. S. Nagamatsu, T. Moriguchi, T. Nagase et al., “A steady operation of n-type organic thin-film transistors with cyano-substituted distyrylbenzene derivative,” Applied Physics Express, vol. 2, no. 10, Article ID 101502, 2009. View at Publisher · View at Google Scholar · View at Scopus
  10. S. Nagamatsu, W. Takashima, T. Okauchi et al., Japan, Europe and United States Patents (PCT/JP2010/053577, EP2405505A1, EP2405505A4, US8674347, US20120001162).
  11. APEX2 Version 2009.9, Bruker AXS Inc., 2009.
  12. SAINT Version 7.68A, Bruker AXS, 2009.
  13. P. Müller, R. Herbst-Irmer, A. Spek, T. Schneider, and M. Sawaya, Crystal Structure Refinement: A Crystallographer's Guide to SHELXL, vol. 7, chapter 7, University of Güttingen, 2002.
  14. G. M. Sheldrick, SADABS Version 2008/1, Bruker AXS Inc., 2008.
  15. G. M. Sheldrick, XPREP Version 2008/2, Bruker AXS Inc, 2008.
  16. G. M. Sheldrick, “Foundations of crystallography,” Acta Crystallographica A, vol. 64, pp. 112–122, 2008. View at Publisher · View at Google Scholar
  17. SHELIXL Version 2013.
  18. D. W. J. Cruickshank, “A detailed refinement of the crystal and molecular structure of anthracene,” Acta Crystallographica, vol. 9, pp. 915–923, 1956. View at Publisher · View at Google Scholar
  19. D. Holmes, S. Kumaraswamy, A. J. Matzger, and K. P. C. Vollhardt, “On the nature of nonplanarity in the [N]phenylenes,” Chemistry A, vol. 5, no. 11, pp. 3399–3412, 1999. View at Publisher · View at Google Scholar · View at Scopus