Chinese Journal of Organic Chemistry >
Utilization of C—H Bond Activation in Synthesis of Organic Semiconductors
Received date: 2016-04-05
Revised date: 2016-05-19
Online 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.
The development of C—H bond activiation and the typical reaction mechanism is introduced in the first part. The progress of organic small molecule and polymer semiconductors prepared by C—H activation is reviewed. The applicability of C—H activation and the performance of organic semiconductors achieved by C—H activation are discussed in detail.
Key words: C—H bond activation; arylation; organic optoelectronic materials
Shi Yanjun , Ni Zhenjie , Zhen Yonggang , Dong Huanli , Hu Wenping . Utilization of C—H Bond Activation in Synthesis of Organic Semiconductors[J]. Chinese Journal of Organic Chemistry, 2016 , 36(8) : 1741 -1764 . DOI: 10.6023/cjoc201604009
[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.
/
〈 |
|
〉 |