The exact molecular structure and the crystal packing of the n-type semiconducting material 3′,3′-(1,4-phenylene)bis{2′-(4′′-trifluoromethyl)phenyl}acrylonitrile was determined by a single crystal X-ray diffraction with twin treatment technique. The air-stable product was crystallized from dichloromethane-hexane mixed solution. The solid-state structure is the example of a typical π-π stacking with side intermolecular CN–H short contact networks. 1. Introduction Organic semiconductors have attracted much attention to offer low-cost, flexible, and throwaway electronic applications, such as organic thin-film transistors (OTFT) and organic solar cells. Since thin-film transistor (TFT) is the most fundamental electronic device in electronic circuit, improvement of OTFT performance is desired [1–3]. Although there are many reports of new candidate organic semiconductor having high mobility, only few reports mentioned drifting characteristics of on-current in OTFTs at on-state [4, 5]. The n-type organic semiconductor with high performance transport characteristics is also strongly desired in organic electronics. Jones and coworkers have succeeded in achieving the air stability to perylenediimide derivatives by cyano (CN) and fluorine (F) substituent [6, 7]. Yasuda et al. reported good p-type transport characteristics in p-phenylenevinylene-type oligomer, which represents the intrinsic stacking functionality by the p-phenylenevinylene structure as distyrylbenzene derivatives. Even in terms of n-type transport simple distyrylbenzene derivatives with electron-withdrawing trifluoromethyl substituents are not reported so far [8]. Recently, we reported excellent n-type transport characteristics of p-phenylenevinylene derivative of 3′,3′-(1,4-phenylene)bis{2′-(4′′-trifluoromethyl)phenyl}acrylonitrile having two cyano (CN) and two trifluoromethyl (CF3) substituents [9]. We also reported the detailed synthetic methods of the compound and its analogues as Japan, Europe, and US patents [10]. Fabricated OTFTs were found to show relative high electron mobility of ca. 10？1？cm2？V？1？s？1 with extremely stable n-type OTFT characteristics. Furthermore, the material has large advantages in terms of the simple procedure via one step synthesis. This should be one good candidate material for n-type organic semiconductor. Herein, we reported X-ray structural determination of the title compound. 2. Materials and Methods The title compound was prepared according to the previous reported literature [10]. Single crystals of
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.
[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.
[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.
[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.
[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.
[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.
[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.
[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.
[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.
[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.
[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.
[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.
