Utilization of C—H Bond Activation in Synthesis of Organic Semiconductors

doi:10.6023/cjoc201604009

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1741-1764.DOI: 10.6023/cjoc201604009 Previous Articles Next Articles

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碳-氢键活化在有机半导体合成方面的应用

石燕君^a,b, 倪振杰^a, 甄永刚^a, 董焕丽^a, 胡文平^a,c

a 中国科学院化学研究所有机固体院重点实验室北京 100190;
b 中国科学院大学北京 100049;
c 天津大学理学院天津 300072

收稿日期:2016-04-05 修回日期:2016-05-19 发布日期:2016-06-01
通讯作者: 甄永刚, 胡文平 E-mail:zhenyg@iccas.ac.cn;huwp@iccas.ac.cn
基金资助:
国家自然科学基金（Nos. 91222203，91233205，51303185）、国家重大科学研究计划（Nos. 2013CB933504，2014CB643600）、中国科学院先导专项（No. XDB12000000）和中国科学院青年创新促进会资助项目.

Utilization of C—H Bond Activation in Synthesis of Organic Semiconductors

Shi Yanjun^a,b, Ni Zhenjie^a, Zhen Yonggang^a, Dong Huanli^a, Hu Wenping^a,c

a Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
b University of the Chinese Academy of Sciences, Beijing 100049;
c College of Science, Tianjin University, Tianjin 30007

Received:2016-04-05 Revised:2016-05-19 Published:2016-06-01
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 91222203, 91233205, 51303185), the Ministry of Science and Technology of China (Nos. 2013CB933504, 2014CB643600), the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB12000000) and the Youth Innovation Promotion Association of Chinese Academy of Sciences.

Cite this article

Shi Yanjun, Ni Zhenjie, Zhen Yonggang, Dong Huanli, Hu Wenping. Utilization of C—H Bond Activation in Synthesis of Organic Semiconductors[J]. Chin. J. Org. Chem., 2016, 36(8): 1741-1764.

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References

[1] Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
[2] (a) Babudri, F.; Cicco, S. R.; Farinola, G. M.; Naso, F.; Bolognesi, A.; Porzio, W. Macromol. Rapid Commun. 1996, 17, 905.
(b) Bao, Z. N.; Chan, W. K.; Yu, L. P. J. Am. Chem. Soc. 1995, 117, 12426.
[3] Kowalski, S.; Allard, S.; Zilberberg, K.; Riedl, T.; Scherf, U. Prog. Polym. Sci. 2013, 38, 1805.
[4] Osedach, T. P.; Andrew, T. L.; Bulovi?, V. Energy Environ. Sci. 2013, 6, 711.
[5] Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976.
[6] Hofmann, A. W. Ber. 1883, 16, 558.
[7] Murahashi, S. J. Am. Chem. Soc. 1955, 77, 6403.
[8] (a) Ohta, A.; Akita, Y.; Ohkuwa, T.; Chiba, M.; Fukunaga, R.; Miyafuji, A.; Nakata, T.; Tani, N.; Aoyagi, Y. Heterocycles 1982, 31, 1951.
(b) Marc, S.; Julien, P.; Emmanuelle, S.; Lemaire, M. Tetrahedron Lett. 1999, 40, 5873.
[9] Mercier, L. G.; Leclerc, M. Acc. Chem. Res. 2013, 46, 1597.
[10] Wang, X. C.; Wang, K.; Wang, M. F. Polym. Chem. 2015, 6, 1846.
[11] Matsidik, R.; Martin, J.; Schmidt, S.; Obermayer, J.; Lombeck, F.; Nubling, F.; Komber, H.; Fazzi, D.; Sommer, M. J. Org. Chem. 2015, 80, 980.
[12] Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
[13] He, C.-Y.; Fan, S.; Zhang, X. J. Am. Chem. Soc. 2010, 132,12850.
[14] Yoon, M. H.; Facchetti, A.; Stern, C. E.; Marks. T. J. J. Am. Chem. Soc. 2006, 128, 5792.
[15] Zhang, J.; Chen, W.; Rojas, A. J.; Jucov, E. V.; Timofeeva, T. V.; Parker, T. C.; Barlow, S.; Marder, S. R. J. Am. Chem. Soc. 2013, 135, 16376.
[16] Pham, M. V.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 3484.
[17] Delord, J. W.; Nimphius, C.; Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 13001.
[18] Review on the synthesis and reactions of dibenzo- [a,e]pentalenes: (a) Saito, M. Symmetry 2010, 2, 950.
(b) Brand, K. Dtsch. Ber. Chem. Ges. 1912, 45, 3071.
(c) Ballester, M.; CastaÇer, J.; Riera, J.; Armet, O. J. Org. Chem. 1986, 51, 1100.
(d) Zhang, H.; Karasawa, T.; Yamada, H.; Wakamiya, A.; Yamaguchi, S. Org. Lett. 2009, 11, 3076.
(e) Levi, Z. U.; Tilley, T. D. J. Am. Chem. Soc. 2009, 131, 2796.
(f) Kawase, T.; Konishi, A.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Kubo, T. Chem. Eur. J. 2009, 15, 2653.
(g) Xu, F.; Peng, L.; Orita, A.; Otera, J. Org. Lett. 2012, 14, 3970.
(h) Jeffrey, J. L.; Sarpong, R. Tetrahedron Lett. 2009, 50, 1969.
(i) Hashmi, A. S. K.; Wieteck, M.; Braun, I.; Nçsel, P.; Jongbloed, L.; Rudolph, M.; Rominger, F. Adv. Synth. Catal. 2012, 354, 555.
[19] Maekawa, T.; Segawa, Y.; Itami, K. Chem. Sci. 2013, 4, 2369.
[20] Zhao, J.; Oniwa, K.; Asao, N.; Yamamoto, Y.; Jin, T. J. Am. Chem. Soc. 2013, 135, 10222.
[21] Kawamata, Y.; Tokuji, S.; Yorimitsu, H.; Osuka, A. Angew. Chem., Int. Ed. 2011, 50, 8867.
[22] (a) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
(b) Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848.
(c) Sun, H. Y.; Gorelsky, S. I.; Stuart, D. R.; Campeau, L. C.; Fagnou, K. J. Org. Chem. 2010, 75, 8180.
(d) Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Org. Chem. 2012, 77, 658.
[23] Mitamura, Y.; Yorimitsu, H.; Oshima, K.; Osuka, A. Chem. Sci. 2011, 2, 2017.
[24] Qian, H. L.; Wang, Z. H.; Y, W.; Zhu, D. B. J. Am. Chem. Soc. 2007, 129, 10664.
[25] Lv, A.; Puniredd, S. R.; Zhang, J.; Li, Z.; Zhu, H.; Jiang, W.; Dong, H.; He, Y.; Jiang, L.; Li, Y.; Pisula, W.; Meng, Q.; Hu, W.; Wang, Z. Adv. Mater. 2012, 24, 2626.
[26] Inganas, O.; Zhang, F.; Andersson, M. R. Acc. Chem. Res. 2009, 42, 1731.
[27] Zhen, Y. G.; Wang, C. R.; Wang, Z. H. Chem. Commun. 2010, 46, 1926.
[28] Zhang, J.; Kang, D.-Y.; Barlow, S.; Marder, S. R. J. Mater. Chem. 2012, 22, 21392.
[29] Liu, S.-Y.; Shi, M.-M.; Huang, J.-C.; Jin, Z.-N.; Hu, X.-L.; Pan, J.-Y.; Li, H.-Y.; Jen, A. K. Y.; Chen, H.-Z. J. Mater. Chem. A 2013, 1, 2795.
[30] Wang, Q. F.; Takita, R.; Kikuzaki, Y.; Ozawa, F. J. Am. Chem. Soc. 2010, 132, 11420.
[31] Rudenko, A. E.; Wiley, C. A.; Stone, S. M.; Tannaci, J. F.; Thompson, B. C. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 3691.
[32] Lu, W.; Kuwabara, J.; Kanbara, T. Macromolecules 2011, 44, 1252.
[33] Fujinami, Y.; Kuwabara, J.; Lu, W.; Hayashi, H.; Kanbara, T. ACS Macro Lett. 2012, 1, 67.
[34] Choi, S. J.; Kuwabara, J.; Kanbara, T. ACS Sustainable Chem. Eng. 2013, 1, 878.
[35] Sharma, A.; Vacchani, D.; Eycken, V. Chem.-Eur. J. 2013, 19, 1158.
[36] Poduval, M. K.; Burrezo, P. M.; Casado, J.; López Navarrete, T. L.; Ortiz, R. P.; Kim, T. H. Macromolecules 2013, 46, 9220.
[37] Kuwabara, J.; Nohara, Y.; Choi, S. J.; Fujinami, Y.; Lu,W.; Yoshimura, K.; Oguma, J.; Suenobu, K.; Kanbara, T. Polym. Chem. 2013, 4, 947.
[38] Nakabayashi, K.; Mori, H. Chem. Lett. 2013, 42, 717.
[39] Morin, P. O.; Bura, T.; Sun, B.; Gorelsky, S. I.; Li, Y.; Leclerc, M. ACS Macro Lett. 2014, 4, 21.
[40] Lombeck, F.; Komber, H.; Gorelsky, S. I.; Sommer, M. ACS Macro Lett. 2014, 3, 819.
[41] Nohara, Y.; Kuwabara, J.; Yasuda, T.; Han, L.; Kanbara, T. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1401.
[42] Luzio, A.; Fazzi, D.; Nübling, F.; Matsidik, R.; Straub, A.; Komber, H.; Giussani, E.; Watkins, S. E.; Barbatti, M.; Thiel, W.; Gann, E.; Thomsen, L.; McNeill, C. R.; Caironi, M.; Sommer, M. Chem. Mater. 2014, 26, 6233.
[43] Rudenko, A. E.; Khlyabich, P. P.; Thompson, B. C. ACS Macro Lett. 2014, 3, 387.
[44] Wang, X.; Wang, M. Polym. Chem. 2014, 5, 5784.
[45] Elsawy, W.; Kang, H.; Yu, K.; Elbarbary, A.; Lee, K.; Lee, J.-S. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2926.
[46] Sun, M. M.; Wang, W.; Liang, L. Y.; Yan, S. H.; Zhou, M. L.; Ling, Q. D. Chin. J. Polym. Sci. 2015, 33, 783.
[47] Kowalski, S.; Allard, S.; Scherf, U. Macromol. Rapid Commun. 2015, 36, 1061.
[48] Homyak, P.; Liu, Y.; Liu, F.; Russel, T. P.; Coughlin, E. B. Macromolecules 2015, 48, 6978.
[49] Matsidik, R.; Komber, H.; Luzio, A.; Caironi, M.; Sommer, M. J. Am. Chem. Soc. 2015, 137, 6705.
[50] Shao, J.; Wang, G.; Wang, K.; Yang, C.; Wang, M. Polym. Chem. 2015, 6, 6836.
[51] Wang, K.; Wang, G.; Wang, M. Macromol. Rapid Commun. 2015, 36, 2162.
[52] Broll, S.; Nübling, F.; Luzio, A.; Lentzas, D.; Komber, H.; Caironi, M.; Sommer, M. Macromolecules 2015, 48, 7481.
[53] Pouliot, J. R.; Sun, B.; Leduc, M.; Najari, A.; Li, Y.; Leclerc, M. Polym. Chem. 2015, 6, 278.
[54] Gao, Y.; Zhang, X.; Tian, H.; Zhang, J.; Yan, D.; Geng, Y.; Wang, F. Adv. Mater. 2015, 27, 6753.
[55] Nakanishi, T.; Shirai, Y.; Han, L. J. Mater. Chem. A 2015, 3, 4229.
[56] Zou, Y.; Najari, A.; Berrouard, S.; Beaupr, S.; Aich, B. R.; Tao, Y.; Leclerc, M. J. Am. Chem. Soc. 2010, 132, 7595.
[57] Piliego, C.; Holcome, T. W.; Douglas, J. D.; Woo, C. H.; Beaujuge, P. M.; Fréchet, J. M. J. J. Am. Chem. Soc. 2010, 132, 7595.
[58] Su, M. S.; Kuo, C. Y.; Yuan, M. C.; Jeng, U. S.; Su, C. J.; Wei, K. H. Adv. Mater. 2011, 23, 3315.
[59] Gendron, D.; Leclerc, M. Energ. Environ. Sci. 2011, 4, 1225.
[60] Chu, T. Y.; Lu, J.; Beaupre, S.; Zhang, Y.; Pouliot, J. R.; Wakim, S.; Zhou, J.; Leclerc, M.; Li, Z.; Ding, J.; Tao, Y. J. Am. Chem. Soc. 2011, 133, 4250.
[61] Guo, X.; Ortiz, R. P.; Zheng, Y.; Hu, Y.; Noh, Y. Y.; Baeg, K. J.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2011, 133, 1405.
[62] Allard, N.; Najari, A.; Pouliot, J.-R.; Pron, A.; Grenier, F.; Leclerc, M. Polym. Chem. 2012, 3, 2875.
[63] Berrouard, P.; Dufresne, S.; Pron, A.; Veilleux, J.; Leclerc, M. J. Org. Chem. 2012, 77, 8167.
[64] Berrouard, P.; Najari, A.; Pron, A.; Gendron, D.; Morin, P. O.; Pouliot, J. R.; Veilleux, J.; Leclerc, M. Angew. Chem., Int. Ed. 2012, 51, 2068.
[65] Grenier, F.; Berrouard, P.; Pouliot, J.-R.; Tseng, H.-R.; Heeger, A. J.; Leclerc, M. Polym. Chem. 2013, 4, 1836.
[66] Pouliot, J. R.; Mercier, L. G.; Caron, S.; Leclerc, M. Macromol. Chem. Phys. 2013, 214, 453.
[67] Wakioka, M.; Ichihara, N.; Kitano, Y.; Ozawa, F. Macromolecules 2014, 47, 626.
[68] Iizuka, E.; Wakioka, M.; Ozawa, F. Macromolecules 2015, 48, 2989.
[69] Lu, W.; Kuwabara, J.; Iijima, T.; Higashimura, H.; Hayashi, H.; Kanbara, T. Macromolecules 2012, 45, 4128.
[70] Wakioka, M.; Kitano, Y.; Ozawa, F. Macromolecule 2013, 46, 370.
[71] Lu, W.; Kuwabara, J.; Kanbara, T. Polym. Chem. 2012, 3, 3217.
[72] Kuramochi, M.; Kuwabara, J.; Lu, W.; Kanbara, T. Macromolecules 2014, 47, 7378.
[73] Lu, W.; Kuwabara, J.; Kuramochi, M.; Kanbara, T. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1396.

碳-氢键活化在有机半导体合成方面的应用

Utilization of C—H Bond Activation in Synthesis of Organic Semiconductors

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