Abstract
Acenes and heteroacenes are receiving great attention in fundamental and applied science due to their interesting optoelectronic and charge transport properties. Their easy synthesis and functionalization have enabled the rapid development of a large number of molecular materials with remarkable charge-transport properties. This perspective provides an overview of their fundamental properties, molecular packing/morphology and charge transport properties and summarizes the progress made in recent years in the development of new high-mobility small-molecule materials focusing in particular on crystalline materials that have been able to approach or surpass mobilities of amorphous silicon.
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H. Minemawari, T. Yamada, H. Matsui, J. Tsutsumi, S. Haas, R. Chiba, R. Kumai, and T. Hasegawa, Nature (London) 475, 364 (2011).
A. Y. Amin, A. Khassanov, K. Reuter, T. Meyer-Friedrichsen, and M. Halik, J. Am. Chem. Soc. 134, 16548 (2012).
E. Menard, V. Podzorov, S.-H. Hur, A. Gaur, M. E. Gershenson, and J. A. Rogers, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 16, 2097 (2004).
O. D. Jurchescu, M. Popinciuc, B. J. Van Wees, and T. T. M. Palstra, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 19, 688 (2007).
C. Reese and Z. Bao, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 19, 4535 (2007).
V. C. Sundar, J. Zaumseil, V. Podzorov, E. Menard, R. L. Willett, T. Someya, M. E. Gershenson, and J. A. Rogers, Science (Washington, D. C.) 303, 1644 (2004).
J. Li, Y. Zhao, H. S. Tan, Y. Guo, C.-A. Di, G. Yu, Y. Liu, M. Lin, S. H. Lim, Y, Zhou, H. Su, and B. S. Ong, Sci. Rep. 2, 754 (2012).
G. R. Desiraju, Crystal Engineering: The Design of Organic Solids (Elsevier Science, Amsterdam, 1989).
J. L. Brédas, J. P. Calbert, D. A. Da Silva Filho, and J. Cornil, Proc. Natl. Acad. Sci. U. S. A. 99, 5804 (2002).
M. D. Curtis, J. Cao, and J. W. Kampf, J. Am. Chem. Soc. 126, 4318 (2004).
V. Coropceanu, J. Cornil, D. A. Da Silva Filho, Y. Olivier, R. Silbey, and J.-L. Brédas, Chem. Rev. 107, 926 (2007).
J. E. Anthony, J. S. Brooks, D. L. Eaton, and S. R. Parkin, J. Am. Chem. Soc. 123, 9482 (2001).
J. E. Anthony, D. L. Eaton, and S. R. Parkin, Org. Lett. 4, 15 (2002).
S. C. B. Mannsfeld, M. L. Tang, and Z. Bao, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 23, 127 (2011).
S. K. Park, T. N. Jackson, J. E. Anthony, and D. A. Mourey, Appl. Phys. Lett. 91, 063517 (2007).
G. Giri, E. Verploegen, S. C. B. Mannsfeld, S. Atahan-Evrenk, D. H. Kim, S. Y. Lee, H. A. Becerril, A. Aspuru-Guzik, M. F. Toney, and Z. Bao, Nature (London) 480, 504 (2011).
G. R. Llorente, M.-B. Dufourg-Madec, D. J. Crouch, R. G. Pritchard, S. Ogier, and S. G. Yeates, Chem. Commun. 21, 3059 (2009).
F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci. 58, 380 (2002).
M. Watanabe, Y. J. Chang, S.-W. Liu, T. H. Chao, K. Goto, I. Minarul, C.-H. Yuan, Y.-T. Tao, T. Shinmyozu, and T. J. Chow, Nat. Chem. 4, 574 (2012).
M. M. Payne, S. R. Parkin, and J. E. Anthony, J. Am. Chem. Soc. 127, 8028 (2005).
H. Meng, M. Bendikov, G. Mitchell, R. Helgeson, F. Wudl, Z. Bao, T. Siegrist, C. Kloc, and C.-H. Chen, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 15, 1090 (2003).
Q. Miao, X. Chi, S. Xiao, R. Zeis, M. Lefenfeld, T. Siegrist, M. L. Steigerwald, and C. Nuckolls, J. Am. Chem. Soc. 128, 1340 (2006).
K. Kobayashi, R. Shimaoka, M. Kawahata, M. Yamanaka, and K. Yamaguchi, Org. Lett. 8, 2385 (2006).
T. Kimoto, K. Tanaka, M. Kawahata, K. Yamaguchi, S. Otsubo, Y. Sakai, Y. Ono, A. Ohno, and K. Kobayashi, J. Org. Chem. 76, 5018 (2011).
H. Moon, R. Zeis, E.-J. Borkent, C. Besnard, A. J. Lovinger, T. Siegrist, C. Kloc, and Z. Bao, J. Am. Chem. Soc. 126, 15322 (2004).
X. Chi, D. Li, H. Zhang, Y. Chen, V. Garcia, C. Garcia, and T. Siegrist, Org. Electron. 9, 234 (2008).
J. Li, M. Wang, S. Ren, X. Gao, W. Hong, H. Li, and D. Zhu, J. Mater. Chem. 22, 10496 (2012).
M. Wang, J. Li, G. Zhao, Q. Wu, Y. Huang, W. Hu, X. Gao, H. Li, and D. Zhu, Adv. Mater. 25, 2229 (2013).
M. C. R. Delgado, K. R. Pigg, D. A. Da Silva Filho, N. E. Gruhn, Y. Sakamoto, T. Suzuki, R. M. Osuna, J. Casado, V. Hernández, J. T. L. Navarrete, N. G. Martinelli, J. Cornil, R. S. Sánchez-Carrera, V. Coropceanu, and J.-L. Brédas, J. Am. Chem. Soc. 131, 1502 (2009).
Y. Sakamoto, T. Suzuki, M. Kobayashi, Y. Gao, Y. Fukai, Y. Inoue, F. Sato, and S. Tokito, J. Am. Chem. Soc. 126, 8138 (2004).
V. Podzorov, V. M. Pudalov, and M. E. Gershenson, Appl. Phys. Lett. 82, 1739 (2003).
V. Podzorov, S. E. Sysoev, E. Loginova, V. M. Pudalov, and M. E. Gershenson, Appl. Phys. Lett. 83, 3504 (2003).
M.-M. Ling, C. Reese, A. L. Briseno, and Z. Bao, Synth. Met. 157, 257 (2007).
W. H. Taylor, Z. Krist. 93, 151 (1936).
S. A. Akopyan, R. L. Avoyan, and Yu. T. Struchkov, Zh. Strukt. Khim. 3, 602 (1962).
D. E. Henn, W. G. Williams, and D. J. Gibbons, J. Appl. Crystallogr. 4, 256 (1971).
I. Bulgarovskaya, V. Vozzhennikov, and S. V. Aleksandrov, Belsky, Latv. PSR Zinat. Akad. Vestis, Fiz. Teh. Zinat., Ser. 4, 53 (1983).
T. Matsukawa, M. Yoshimura, K. Sasai, M. Uchiyama, M. Yamagishi, Y. Tominari, Y. Takahashi, J. Takeya, Y. Kitaoka, Y. Mori, and T. Sasaki, J. Cryst. Growth 312, 310 (2010).
S. Bergantin and M. Moret, Cryst. Growth Des. 12, 6035 (2012).
G. Schuck, S. Haas, A. F. Stassen, H.-J. Kirner, and B. Batlogg, Acta Crystallogr., Sect. E 63, 02893 (2007).
S. Haas, A. F. Stassen, G. Schuck, K. P. Pernstich, D. J. Gundlach, B. Batlogg, U. Berens, and H.-J. Kirner, Phys. Rev B: Condens. Matter 76, 115203 (2007).
K. A. McGarry, W. Xie, C. Sutton, C. Risko, Y. Wu, V.G. Young, J.-L. Brédas, C. D. Frisbie, and C. J. Douglas, Chem. Mater. 25, 2254 (2013).
W. Xie, K. A. McGarry, F. Liu, Y. Wu, P. P. Ruden, C. J. Douglas, and C. D. Frisbie, J. Phys. Chem. C 117, 11522 (2013).
K. Takimiya, M. Nakano, M. J. Kang, E. Miyazaki, and I. Osaka, Eur. J. Org. Chem. 2013, 217 (2013).
W. Jiang, Y. Li, and Z. Wang, Chem. Soc. Rev. 42, 6113 (2013).
K. Takimiya, S. Shinamura, I. Osaka, and E. Miyazaki, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 23, 4347 (2011).
J. G. Laquindanum, H. E. Katz, and A. J. Lovinger, J. Am. Chem. Soc. 120, 664 (1998).
M. M. Payne, S. R. Parkin, J. E. Anthony, C.-C. Kuo, and T. N. Jackson, J. Am. Chem. Soc. 127, 4986 (2005).
S. Subramanian, S. K. Park, S. R. Parkin, V. Podzorov, T. N. Jackson, and J. E. Anthony, J. Am. Chem. Soc. 130, 2706 (2008).
O. D. Jurchescu, S. Subramanian, R. J. Kline, S.D. Hudson, J. E. Anthony, T. N. Jackson, and D. J. Gundlach, Chem. Mater. 20, 6733 (2008).
Y. Mei, M. A. Loth, M. Payne, W. Zhang, J. Smith, C. S. Day, S. R. Parkin, M. Heeney, I. McCulloch, T. D. Anthopoulos, J. E. Anthony, and O. D. Jurchescu, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 25, 4352 (2013).
H. Ebata, T. Izawa, E. Miyazaki, K. Takimiya, M. Ikeda, H. Kuwabara, and T. Yui, J. Am. Chem. Soc. 129, 15732 (2007).
T. Uemura, Y. Hirose, M. Uno, K. Takimiya, and J. Takeya, Appl. Phys. Express 2, 111501 (2009).
C. Liu, T. Minari, X. Lu, A. Kumatani, K. Takimiya, and K. Tsukagoshi, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 23, 523 (2011).
S. Haas, Y. Takahashi, K. Takimiya, and T. Hasegawa, Appl. Phys. Lett. 95, 022111 (2009).
W. Xie, K. Willa, Y. Wu, R. Häusermann, K. Takimiya, B. Batlogg, and C. D. Frisbie, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 25, 3478 (2013).
A. N. Sokolov, S. Atahan-Evrenk, R. Mondal, H. B. Akkerman, R. S. Sánchez-Carrera, S. Granados-Focil, J. Schrier, S. C Mannsfeld, A. P. Zoombelt, and Z. Bao, Nat. Commun. 2, 437 (2011).
M. J. Kang, E. Miyazaki, I. Osaka, K. Takimiya, and A. Nakao, ACS Appl. Mater. Interfaces 5, 2331 (2013).
Y. S. Yang, T. Yasuda, H. Kakizoe, H. Mieno, H. Kino, Y. Tateyama, and C. Adachi, Chem. Commun. 49, 6483 (2013).
T. Okamoto, C. Mitsui, M. Yamagishi, K. Nakahara, J. Soeda, Y. Hirose, K. Miwa, H. Sato, A. Yamano, T. Matsushita, T. Uemura, and J. Takeya, Adv. Mater. (Weinheim, Fed. Repub. Ger.) 25, 6395 (2013).
Y. Miyata, E. Yoshikawa, T. Minari, K. Tsukagoshi, and S. Yamaguchi, J. Mater. Chem. 22, 7715 (2012).
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Yassar, A. Recent trends in crystal engineering of high-mobility materials for organic electronics. Polym. Sci. Ser. C 56, 4–19 (2014). https://doi.org/10.1134/S1811238214010111
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DOI: https://doi.org/10.1134/S1811238214010111