Organic Reactions in Covalent Functionalization of Graphene

doi:10.6023/cjoc202004022

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3279-3288.DOI: 10.6023/cjoc202004022 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

石墨烯共价修饰中的有机反应

郝冰洁^a,b,c, 宋涛^a, 黄晓宇^b,c, 叶茂^a, 钱文昊^a

a 上海市徐汇区牙病防治所上海 200032;
b 上海科技大学物质科学与技术学院上海 201210;
c 中国科学院上海有机化学研究所上海 200032

收稿日期:2020-04-14 修回日期:2020-05-04 发布日期:2020-05-11
通讯作者: 黄晓宇, 钱文昊 E-mail:pingyanlaoto@163.com;xyhuang@mail.sioc.ac.cn
基金资助:
国家自然科学基金（No.51773222）、上海市自然科学基金（No.20ZR1452200）、上海市徐汇区科学技术委员会（No.SHXH201613）、上海市徐汇区医学尖峰学科（No.SHXH201706）、上海市医学领军人才（No.2019LJ27）和上海市医学重点专科（No.ZK2019B12）资助项目.

Organic Reactions in Covalent Functionalization of Graphene

Hao Bingjie^a,b,c, Song Tao^a, Huang Xiaoyu^b,c, Ye Mao^a, Qian Wenhao^a

a Department of Stomatology, Shanghai Xuhui District Dental Center, Shanghai 200032;
b Shanghaitech University, School of Physical Science and Technology, Shanghai 201210;
c Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032

Received:2020-04-14 Revised:2020-05-04 Published:2020-05-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51773222), the Shanghai Scientific and Technological Innovation Project (No. 20ZR1452200), the Scientific Research Project of Science and Technology Commission of Xuhui Municipality (No. SHXH201613), the Scientific Research Project of Xuhui Provincial Commission of Health and Family Planning (No. SHXH201706), the Program for Outstanding Medical Academic Leader (No. 2019LJ27) and the Shanghai Medical Key Specialty (No. ZK2019B12).

Graphene and graphene oxide possess unique structure and excellent properties, and have become popular potential materials in biology, information, energy and other fields in recent years. The high-quality nanocomposites were obtained by hybridizing graphene-based materials with functional molecules, polymers and nanoparticles. Besides the modification via weak interaction, covalent modification of graphene and graphene oxide via organic reaction can stably and effectively optimize the structure, enhance their performances and extend their applications. In this review, the diverse approaches of chemically covalent modification of graphene and graphene oxide are reviewed via esterification, acylation, Williamson reaction, Eschenmoser-Claisen[3,3] σ rearrangement and click chemistry, and the future development trend is prospected.

Key words: graphene, graphene oxide, covalent functionalization, organic reactions

Cite this article

Hao Bingjie, Song Tao, Huang Xiaoyu, Ye Mao, Qian Wenhao. Organic Reactions in Covalent Functionalization of Graphene[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3279-3288.

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References

[1] Peierls, R. E. Ann. Inst. Henri Poincare, Sect. A 1935, 5, 177.
[2] Mermin, N. D. Phys. Rev. 1968, 176, 250.
[3] Novoselov, K. S.; Geim, A. K.; Morozov, S. V.; Grigorieva, I. V.; Firsov, A. Science 2004, 306, 666.
[4] Geim, A. K.; Novoselov, K. S. Nat. Mater. 2007, 6, 183.
[5] Novoselov, K. S.; Falko, V. I.; Colombo, L.; Gellert, P. R.; Schwab, M. G.; Kim, K. Nature 2012, 490, 192.
[6] Geim, A. K. Science 2009, 324, 1530.
[7] Zhu, Y. W.; Murali, S.; Cai, W. W.; Li, X. S.; Suk, J. W.; Potts, J. R.; Ruoff, R. S. Adv. Mater. 2010, 22, 3906.
[8] Lee, C.; Wei, X.; Kysar, J. W.; Hone, J. Science 2008, 321, 385.
[9] Niimi, Y.; Matsui, T.; Kambara, H.; Tagami, K.; Tsukadaand, M.; Fukuyama, H. Phys. Rev. B: Condens. Matter Mater. Phys. 2006, 73, 085421.
[10] Balandin, A. A.; Ghosh, S.; Bao, W. Z.; Calizo, I.; Teweldebrhan, D.; Miao, F.; Lau, C. N. Nano Lett. 2008, 8, 902.
[11] Berger, C.; Song, Z. M.; Li, T. B.; Li, X. B.; Ogbazghi, A. Y.; Feng, R.; Dai, Z. T.; Marchenkov, A. N.; Conrad, E H.; First, P. N.; de Heer, W. A. J. Phys. Chem. B 2004, 108, 19912.
[12] Schedin, F.; Geim, A. K.; Morozov, S. V.; Hill, E. W.; Blake, P.; Katsnelson, M. I.; Novoselov, K. S. Nat. Mater. 2007, 6, 652.
[13] Li, Z. Y.; Zhang, W. H.; Luo, Y.; Yang, J. L.; Hou, J. G. J. Am. Chem. Soc. 2009, 131, 6320.
[14] Stankovich, S.; Piner, R. D.; Nguyen, S. T.; Ruoff, R. S. Carbon 2006, 44, 3342.
[15] Titelman, G. I.; Gelman, V.; Bron, S.; Khalfin, R. L.; Cohen, Y.; Bianco-Peled, H. Carbon 2005, 43, 641.
[16] Szabo, T.; Tombacz, E.; Illes, E.; Dekany, I. Carbon 2006, 44, 537.
[17] He, H., Riedl, T., Lerf, A.; Klinowski, J. J. Phys. Chem. 1996, 100, 19954.
[18] Misra, S. K.; Kondaiah, P.; Bhattacharya, S.; Rao, C. N. R. Small 2012, 8,131.
[19] Song, Y.; Wei, W.; Qu, X. Adv. Mater. 2011, 23, 4215.
[20] Li, J. L.; Bao, H. C.; Hou, X. L.; Sun, X.; Wang, G.; Gu, M. Angew. Chem., Int. Ed. 2012, 51, 1830.
[21] Shao, Y.; Wang, J.; Wu, H.; Liu, J.; Aksay, I. A.; Lin, Y. Electro- analysis 2010, 22, 1027.
[22] Szabó, T.; Berkesi, O.; Forgó, P.; Josepovits, K.; Sanakis, Y.; Petridis, D.; Dékány, I. Chem. Mater. 2006, 18, 2740.
[23] Lerf, A.; He, H.; Riedl, T.; Forster, M.; Klinowski, J. Solid State Ionics 1997, 101~103, 857.
[24] Dua, V.; Surwade, S. P.; Ammu, S.; Agnihotra, S. R.; Jain, S.; Roberts, K. E.; Park, S.; Ruoff, R. S.; Manohar, S. K. Angew. Chem., Int. Ed. 2010, 49, 2154.
[25] David, L.; Bhandavat, R.; Singh, G. ACS Nano 2014, 8, 1759.
[26] Shamsipur, M.; Molaei, K.; Molaabasi, F.; Hosseinkhani, S.; Taherpour, A.; Sarparast, M.; Moosavifard, S. E.; Barati, A. ACS Appl. Mater. Interfaces 2019, 11, 46077.
[27] Cao, Y.; Lai, Z.; Feng, J.; Wu, P. J. Mater. Chem. 2011, 21, 9271.
[28] Xu, Z. Y.; Li, Y. J.; Shi, P.; Wang, B. J.; Huang, X. Y. Chin. J. Org. Chem. 2013, 33, 573(in Chinese). (徐志远, 李永军, 史萍, 王博婵, 黄晓宇, 有机化学, 2013, 33, 573.)
[29] Dai, J.; Lang, M. D. Acta Chem. Sinica 2012, 70, 1237(in Chinese). (戴静, 郎美东, 化学学报, 2012, 70, 1237.)
[30] Xu, Z. Y.; Wang, S.; Li, Y. J.; Wang, M. W.; Shi, P.; Huang, X. Y. ACS Appl. Mater. Interfaces 2014, 6, 17268.
[31] Stankovich, S.; Piner, R. D.; Chen, X.; Wu, N.; Ruoff, R. S. J. Mater. Chem. 2006,16, 155.
[32] Bai, H.; Li, C.; Wang, X.; Shi, G. Chem. Commun. 2010, 46, 2376.
[33] Yoon, S.; In, I. J. Mater. Sci. 2011, 46, 1316.
[34] Cano, M.; Khan, U.; Sainsbury, T.; Neill, A. O.; Wang, Z.; McGovern, I. T.; Maser, W. K.; Benito, A. M.; Coleman, J. N. Carbon 2013, 52, 363.
[35] Vacchi, I. A.; Raya, J.; Bianco, A.; Ménard-Moyon, C. 2D Mater. 2018, 5, 035037.
[36] Ji, P.; Zhang, W.; Ai, S.; Zhang, Y.; Liu, J.; Liu, J.; He, P.; Li, Y. Nanotechnology 2019, 30, 115701.
[37] Sydlik, S. A.; Swager, T. M. Adv. Funct. Mater. 2013, 23, 1873.
[38] Vacchi, I. A.; Spinato, C.; Raya, J.; Bianco, A.; Ménard-Moyon, C. Nanoscale 2016, 8, 13714.
[39] Sinitskii, A.; Dimiev, A.; Corley, D. A.; Fursina, A. A.; Kosynkin, D. V.; Tour, J. M. ACS Nano 2010, 4, 1949.
[40] Hamilton, C. E.; Lomeda, J. R.; Sun, Z. Z.; Tour, J. M.; Barron, A. R. Nano Lett. 2009, 9, 3460.
[41] Deng, Y.; Li, Y. J.; Dai, J.; Lang, M. D.; Huang, X. Y. J. Polym. Sci. Part A:Polym. Chem. 2011, 49, 4747.
[42] Georgakilas, V.; Bourlinos, A. B.; Zboril, R.; Steriotis, T. A.; Dallas, P.; Stubos, A. K.; Trapalis, C. Chem. Commun. 2010, 46, 1766.
[43] Vadukumpully, S.; Gupta, J.; Zhang, Y.; Xu, C. Q.; Valiyaveettil, S. Nanoscale 2011, 3, 303.
[44] Nemes-Incze, P.; Osváth, Z.; Kamarás, K.; Biro, L. P. Carbon 2008, 46, 1435.
[45] Zhang, X.; Hou, L.; Cnossen, A.; Coleman, A. C.; Ivashenko, O.; Rudolf, P.; van Wees, B. J.; Browne, W. R.; Feringa, B. L. Chem.-Eur. J. 2011, 17, 8957.
[46] Quintana, M.; Spyrou, K.; Grzelczak, M.; Browne, W. R.; Rudolf, P.; Prato, M. ACS Nano 2010, 4, 3527.
[47] Liu, L. H.; Lerner, M. M.; Yan, M. Nano Lett. 2010, 10, 3754.
[48] Zhong, X.; Jin, J.; Li, S.; Niu, Z.; Hu, W.; Li, R.; Ma, J. Chem. Commun. 2010, 46, 7340.
[49] Loh, K. P.; Bao, Q.; Anga, P. K. Yang, J. X. J. Mater. Chem. 2010, 20, 2277.
[50] Salavagione, H. J.; Martínez, G.; Ellis, G. Macromol. Rapid. Commun. 2011, 32, 1771.
[51] Liu, Y.; Zhou, J.; Zhang, X.; Liu, Z.; Wan, X.; Tian, J.; Wang, T.; Chen, Y. Carbon 2009, 47, 3113.
[52] Yu, D.; Yang, Y.; Durstock, M.; Baek, J. B.; Dai, L. ACS Nano 2010, 4, 5633.
[53] Collins, W. R.; Lewandowski, W.; Schmois, E.; Walish, J.; Swager, T. M. Angew. Chem., Int. Ed. 2011, 50, 8848.
[54] Palaganas, J. O.; Palaganas, N. B.; Ramos, L. J. I.; David, C. P. C. ACS Appl. Mater. Interfaces 2019, 11, 46034.
[55] Yang, H.; Shan, C.; Li, F.; Han, D.; Zhang, Q.; Niu, L. Chem. Commun. 2009, 26, 3880.
[56] Collins, W. R.; Schmois, E.; Swager, T. M. Chem. Commun. 2011, 47, 8790.
[57] Cao, Y.; Lai, Z.; Feng, J.; Wu, P. J. Mater. Chem. 2011, 21, 9271.
[58] Liu, Z.; Robinson, J. T.; Sun, X.; Dai, H. J. Am. Chem. Soc. 2008, 130, 10876.
[59] Lee, S. H.; Kim, H. W.; Hwang, J. O.; Lee, W. J.; Kwon, J.; Bielawski, C. W.; Ruoff, R. S.; Kim, S. O. Angew. Chem., Int. Ed. 2010, 49, 10084.
[60] Wang, D.; Ye, G.; Wang, X.; Wang, X. Adv. Mater. 2011, 23, 1122.
[61] Fang, M.; Wang, K.; Lu, H. B.; Yang, Y. L.; Nutt, S. J. Mater. Chem. 2009, 19, 7098.
[62] Lee, S. H.; Dreyer, D. R.; An, J.; Velamakanni, A.; Piner, R. D.; Park, S.; Zhu, Y.; Kim, S. O.; Bielawski, C. W.; Ruoff, R. S. Macromol. Rapid. Commun. 2010, 31, 281.
[63] Liu, Z. Z.; Zhu, S. J.; Li, Y. J.; Li, Y. S.; Shi, P.; Huang, Z.; Huang, X. Y. Polym. Chem. 2015, 6, 311.
[64] Huang, Y.; Qin, Y.; Zhou, Y.; Niu, H.; Yu, Z. Z.; Dong, J. Y. Chem. Mater. 2010, 22, 4096.
[65] Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 44, 2004.
[66] Becer, C. R.; Hoogenboom, R.; Schubert, U. S. Angew. Chem., Int. Ed. 2009, 48, 4900.
[67] Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928.
[68] Helms. B.; Mynar, J. L.; Hawker, C. J.; Frechet, J. M. J. Am. Chem. Soc. 2004, 126, 15020.
[69] John, E.; Moses, A.; Moorhouse, D. Chem. Rev. 2007, 36, 1249.
[70] Zhang, T.; Zheng, C. H.; Ding, X. B.; Peng, Y. X. Prog. Chem. 2008, 20, 1090 (in Chinese). (张涛, 郑朝辉, 成煦, 丁小斌, 彭宇行, 化学进展, 2008, 20, 1090.)
[71] He, H.; Gao, C. Chem. Mater. 2010, 22, 5054.
[72] Shen, J.; Hu, Y.; Li, C.; Qin, C.; Ye, M. S Small 2009, 5, 82.
[73] Pan, Y.; Bao, H.; Sahoo, N. G.; Wu, T.; Li, L. Adv. Funct. Mater. 2011, 21, 2754.
[74] Imani, R.; Prakash, S.; Vali, H.; Faghihi, S. Biomater. Sci. 2018, 6, 1636.
[75] Guo, S.; Nishina, Y.; Bianco, A.; Cécilia, M.-M. Angew. Chem., Int. Ed. 2020, 59, 1542.

石墨烯共价修饰中的有机反应

Organic Reactions in Covalent Functionalization of Graphene

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