通过Scholl反应合成螺烯类纳米碳分子的研究进展
收稿日期: 2021-07-30
修回日期: 2021-09-23
网络出版日期: 2021-09-30
基金资助
国家自然科学基金(21901128); 国家自然科学基金(22071120); 国家重点研发计划(2020YFA0711500); 中央高校基本科研业务费专项资金资助项目
Recent Advances in the Syntheses of Helicene-Based Molecular Nanocarbons via the Scholl Reaction
Received date: 2021-07-30
Revised date: 2021-09-23
Online published: 2021-09-30
Supported by
National Natural Science Foundation of China(21901128); National Natural Science Foundation of China(22071120); National Key R&D Program of China(2020YFA0711500); Fundamental Research Funds for the Central Universities
近年来, 通过有机合成方式构建的结构精确的纳米碳材料备受关注, 展现出独特的性质和广阔的应用前景. 将具有螺旋手性的螺烯与大尺寸的分子基纳米碳结合, 产生了一类独特的手性纳米碳分子, 在手性光学、手性光电子学及自旋电子学等领域具有潜在的应用价值. 然而, 由于其特殊的螺旋结构及分子内较大的张力, 这类纳米碳分子的合成颇具挑战. 在合成螺烯类纳米碳分子的几类常用方法中, Scholl反应条件温和且十分高效, 被广泛使用. 从合成的角度出发, 详细综述了通过Scholl反应构建螺烯类纳米碳分子的研究进展, 并对该领域未来的发展提出展望.
陈星宇 , 李继坤 , 王小野 . 通过Scholl反应合成螺烯类纳米碳分子的研究进展[J]. 有机化学, 2021 , 41(11) : 4105 -4137 . DOI: 10.6023/cjoc202107063
Molecular nanocarbon materials with well-defined structures constructed through organic synthesis have attracted much attention in recent years, exhibiting unique properties and broad applications in many areas. The combination of helicenes and molcular nanocarbons generates a fancinating type of chiral molecular nanocarbons with potential applications in the fields of chiral optics, chiral optoelectronics and spintronics etc. However, it is of greart challenge to synthesize these molecules due to the large intramolecular strain and the special helical structure. Among various synthetic strategies, the Scholl reaction possesses the advantages of mild conditions and high efficiency. In this review, recent advances in the syntheses of helicene-based molecular nanocarbons via the Scholl reaction are summarized, and our perspectives to stimulate further development of the chiral nanocarbon materials are also provided.
| [1] | Said, A. A.; Xie, J.; Zhang, Q. Small 2019, 15, 1900854. |
| [2] | Edwards, R. S.; Coleman, K. S. Nanoscale 2013, 5, 38. |
| [3] | Yan, Y.; Miao, J.; Yang, Z.; Xiao, F. X.; Yang, H. B.; Liu, B.; Yang, Y. Chem. Soc. Rev. 2015, 44, 3295. |
| [4] | Jariwala, D.; Sangwan, V. K.; Lauhon, L. J.; Marks, T. J.; Hersam, M. C. Chem. Soc. Rev. 2013, 42, 2824. |
| [5] | Wu, Z.; Wang, Y.; Liu, X.; Lv, C.; Li, Y.; Wei, D.; Liu, Z. Adv. Mater. 2019, 31, 1800716. |
| [6] | Léonard, F.; Talin, A. A. Nat. Nanotechnol. 2011, 6, 773. |
| [7] | Huang, X.; Qi, X.; Boey, F.; Zhang, H. Chem. Soc. Rev. 2012, 41, 666. |
| [8] | Wang, Y.; Li, Z.; Wang, J.; Li, J.; Lin, Y. Trends Biotechnol. 2011, 29, 205. |
| [9] | Li, Y.; Xu, L.; Liu, H.; Li, Y. Chem. Soc. Rev. 2014, 43, 2572. |
| [10] | Narita, A.; Wang, X.-Y.; Feng, X.; Müllen, K. Chem. Soc. Rev. 2015, 44, 6616. |
| [11] | Fernández-García, J. M.; Evans, P. J.; Filippone, S.; Herranz, M. Á.; Martín, N. Acc. Chem. Res. 2019, 52, 1565. |
| [12] | Márquez, I. R.; Castro-Fernández, S.; Millán, A.; Campaña, A. G. Chem. Commun. 2018, 54, 6705. |
| [13] | Wang, X.-Y.; Yao, X.; Müllen, K. Sci. China Chem. 2019, 62, 1099. |
| [14] | Shen, Y.; Chen, C.-F. Chem. Rev. 2012, 112, 1463. |
| [15] | Gingras, M. Chem. Soc. Rev. 2013, 42, 968. |
| [16] | Gingras, M.; Félix, G.; Peresutti, R. Chem. Soc. Rev. 2013, 42, 1007. |
| [17] | Gingras, M. Chem. Soc. Rev. 2013, 42, 1051. |
| [18] | Li, C.; Yang, Y.; Miao, Q. Chem. Asian J. 2018, 13, 884. |
| [19] | Dhbaibi, K.; Favereau, L.; Crassous, J. Chem. Rev. 2019, 119, 8846. |
| [20] | Liu, B.; Zhang, Y.; Chen, Y.; Liu, X.; Zhang, L. Chin. J. Org. Chem. 2020, 40, 2879. (in Chinese) |
| [20] | (刘秉康, 张艳丽, 陈瑜, 刘旭光, 张磊, 有机化学, 2020, 40, 2879.) |
| [21] | Xu, W.; Wu, L.; Fang, M.; Ma, Z.; Shan, Z.; Li, C.; Wang, H., J. Org. Chem. 2017, 82, 11192. |
| [22] | Liu, X.; Sun, H.; Xu, W.; Wan, S.; Shi, J.; Li, C.; Wang, H. Org. Chem. Front. 2018, 5, 1257. |
| [23] | Wang, J.; Wang, G.; Li, C.; Dong, Y.; Ma, Z.; Wang, H. J. Org. Chem. 2021, 86, 4413. |
| [24] | Wang, X.-Y.; Wang, X. C.; Narita, A.; Wagner, M.; Cao, X. Y.; Feng, X.; Müllen, K. J. Am. Chem. Soc. 2016, 138, 12783. |
| [25] | Wang, X.-Y.; Narita, A.; Zhang, W.; Feng, X.; Müllen, K. J. Am. Chem. Soc. 2016, 138, 9021. |
| [26] | Schuster, N. J.; Hernández Sánchez, R.; Bukharina, D.; Kotov, N. A.; Berova, N.; Ng, F.; Steigerwald, M. L.; Nuckolls, C. J. Am. Chem. Soc. 2018, 140, 6235. |
| [27] | Ma, Z.; Winands, T.; Liang, N.; Meng, D.; Jiang, W.; Doltsinis, N. L.; Wang, Z. Sci. China Chem. 2019, 63, 208. |
| [28] | Liu, B.; Böckmann, M.; Jiang, W.; Doltsinis, N. L.; Wang, Z. J. Am. Chem. Soc. 2020, 142, 7092. |
| [29] | Liu, G.; Koch, T.; Li, Y.; Doltsinis, N. L.; Wang, Z. Angew. Chem., nt. Ed. 2019, 58, 178. |
| [30] | Hosokawa, T.; Takahashi, Y.; Matsushima, T.; Watanabe, S.; Kikkawa, S.; Azumaya, I.; Tsurusaki, A.; Kamikawa, K. J. Am. Chem. Soc. 2017, 139, 18512. |
| [31] | Yubuta, A.; Hosokawa, T.; Gon, M.; Tanaka, K.; Chujo, Y.; Tsurusaki, A.; Kamikawa, K. J. Am. Chem. Soc. 2020, 142, 10025. |
| [32] | Zhang, F.; Michail, E.; Saal, F.; Krause, A. M.; Ravat, P. Chem.- Eur. J. 2019, 25, 16241. |
| [33] | Roy, M.; Berezhnaia, V.; Villa, M.; Vanthuyne, N.; Giorgi, M.; Naubron, J. V.; Poyer, S.; Monnier, V.; Charles, L.; Carissan, Y.; Hagebaum-Reignier, D.; Rodriguez, J.; Gingras, M.; Coquerel, Y. Angew. Chem., nt. Ed. 2020, 59, 3264. |
| [34] | Grzybowski, M.; Skonieczny, K.; Butenschön, H.; Gryko, D. T. Angew. Chem., nt. Ed. 2013, 52, 9900. |
| [35] | Grzybowski, M.; Sadowski, B.; Butenschön, H.; Gryko, D. T. Angew. Chem., nt. Ed. 2020, 59, 2998. |
| [36] | Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718. |
| [37] | Rempala, P.; Kroulík, J.; King, B. T. J. Org. Chem. 2006, 71, 5067. |
| [38] | Zhai, L.; Shukla, R.; Wadumethrige, S. H.; Rathore, R. J. Org. Chem. 2010, 75, 4748. |
| [39] | Rempala, P.; Kroulík, J.; King, B. T. J. Am. Chem. Soc. 2004, 126, 15002. |
| [40] | Liu, J.; Narita, A.; Osella, S.; Zhang, W.; Schollmeyer, D.; Beljonne, D.; Feng, X.; Müllen, K. J. Am. Chem. Soc. 2016, 138, 2602. |
| [41] | Pradhan, A.; Dechambenoit, P.; Bock, H.; Durola, F. J. Org. Chem. 2013, 78, 2266. |
| [42] | Fang, L.; Lin, W.; Shen, Y.; Chen, C.-F. Chin. J. Org. Chem. 2018, 38, 541. (in Chinese) |
| [42] | (房蕾, 林伟彬, 沈赟, 陈传峰, 有机化学, 2018, 38, 541.) |
| [43] | Evans, P. J.; Ouyang, J.; Favereau, L.; Crassous, J.; Fernández, I.; Perles, J.; Martín, N. Angew. Chem.. Int. Ed. 2018, 57, 6774. |
| [44] | Martin, M. M.; Hampel, F.; Jux, N. Chem.-Eur. J. 2020, 26, 10210. |
| [45] | Xu, Q.; Wang, C.; He, J.; Li, X.; Wang, Y.; Chen, X.; Sun, D.; Jiang, H. Org. Chem. Front. 2021, 8, 2970. |
| [46] | Chen, Y.; Lin, C.; Luo, Z.; Yin, Z.; Shi, H.; Zhu, Y.; Wang, J. Angew. Chem., nt. Ed. 2021, 60, 7796. |
| [47] | Tanaka, H.; Inoue, Y.; Mori, T. ChemPhotoChem 2018, 2, 386. |
| [48] | Mori, T. Chem. Rev. 2021, 121, 2373. |
| [49] | Zhao, W.-L.; Li, M.; Lu, H.-Y.; Chen, C.-F. Chem. Commun. 2019, 55, 13793. |
| [50] | Qiu, Z.; Ju, C. W.; Frédéric, L.; Hu, Y.; Schollmeyer, D.; Pieters, G.; Müllen, K.; Narita, A. J. Am. Chem. Soc. 2021, 143, 4661. |
| [51] | Cruz, C. M.; Márquez, I. R.; Mariz, I. F. A.; Blanco, V.; Sánchez- Sánchez, C.; Sobrado, J. M.; Martín-Gago, J. A.; Cuerva, J. M.; Maçôas, E.; Campaña, A. G. Chem. Sci. 2018, 9, 3917. |
| [52] | Cruz, C. M.; Castro-Fernández, S.; Maçôas, E.; Cuerva, J. M.; Campaña, A. G. Angew. Chem., nt. Ed. 2018, 57, 14782. |
| [53] | Medel, M. A.; Tapia, R.; Blanco, V.; Miguel, D.; Morcillo, S. P.; Campaña, A. G. Angew. Chem., nt. Ed. 2021, 60, 6094. |
| [54] | Medel, M. A.; Cruz, C. M.; Miguel, D.; Blanco, V.; Morcillo, S. P.; Campaña, A. G. Angew. Chem., nt. Ed. 2021, 60, 22051. |
| [55] | Reger, D.; Haines, P.; Heinemann, F. W.; Guldi, D. M.; Jux, N. Angew. Chem., nt. Ed. 2018, 57, 5938. |
| [56] | Reger, D.; Haines, P.; Amsharov, K. Y.; Schmidt, J. A.; Ullrich, T.; Bönisch, S.; Hampel, F.; Görling, A.; Nelson, J.; Jelfs, K. E.; Guldi, D. M.; Jux, N. Angew. Chem., nt. Ed. 2021, 60, 18073. |
| [57] | Dusold, C.; Sharapa, D. I.; Hampel, F.; Hirsch, A. Chem.-Eur. J. 2021, 27, 2332. |
| [58] | Luo, J.; Xu, X.; Mao, R.; Miao, Q. J. Am. Chem. Soc. 2012, 134, 13796. |
| [59] | Li, C.; Wu, H.; Zhang, T.; Liang, Y.; Zheng, B.; Xia, J.; Xu, J.; Miao, Q. Chem 2018, 4, 1416. |
| [60] | Shan, L.; Liu, D.; Li, H.; Xu, X.; Shan, B.; Xu, J. B.; Miao, Q. Adv. Mater. 2015, 27, 3418. |
| [61] | Li, C.; Wang, Y.; Zhang, T.; Zheng, B.; Xu, J.; Miao, Q. Chem. Asian J. 2019, 14, 1676. |
| [62] | Arslan, H.; Uribe-Romo, F. J.; Smith, B. J.; Dichtel, W. R. Chem. Sci. 2013, 4, 3973. |
| [63] | Niu, W.; Fu, Y.; Komber, H.; Ma, J.; Feng, X.; Mai, Y.; Liu, J. Org. Lett. 2021, 23, 2069. |
| [64] | Fujikawa, T.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2015, 137, 7763. |
| [65] | Fujikawa, T.; Mitoma, N.; Wakamiya, A.; Saeki, A.; Segawa, Y.; Itami, K. Org. Biomol. Chem. 2017, 15, 4697. |
| [66] | Fujikawa, T.; Segawa, Y.; Itami, K. J. Org. Chem. 2017, 82, 7745. |
| [67] | Hossain, M. M.; Thakur, K.; Talipov, M. R.; Lindeman, S. V.; Mirzaei, S.; Rathore, R. Org. Lett. 2021, 23, 5170. |
| [68] | Sun, Z.; Yi, C.; Liang, Q.; Bingi, C.; Zhu, W.; Qiang, P.; Wu, D.; Zhang, F. Org. Lett. 2020, 22, 209. |
| [69] | Urieta-Mora, J.; Krug, M.; Alex, W.; Perles, J.; Fernández, I.; Molina-Ontoria, A.; Guldi, D. M.; Martín, N. J. Am. Chem. Soc. 2020, 142, 4162. |
| [70] | Tanaka, H.; Ikenosako, M.; Kato, Y.; Fujiki, M.; Inoue, Y.; Mori, T. Commun. Chem. 2018, 1, 38. |
| [71] | Hu, Y.; Wang, X.-Y.; Peng, P.-X.; Wang, X.-C.; Cao, X.-Y.; Feng, X.; Müllen, K.; Narita, A. Angew. Chem., nt. Ed. 2017, 56, 3374. |
| [72] | Hu, Y.; Paternò, G. M.; Wang, X.-Y.; Wang, X.-C.; Guizzardi, M.; Chen, Q.; Schollmeyer, D.; Cao, X.-Y.; Cerullo, G.; Scotognella, F.; Müllen, K.; Narita, A. J. Am. Chem. Soc. 2019, 141, 12797. |
| [73] | Chang, H.; Liu, H.; Dmitrieva, E.; Chen, Q.; Ma, J.; He, P.; Liu, P.; Popov, A. A.; Cao, X.-Y.; Wang, X.-Y.; Zou, Y.; Narita, A.; Müllen, K.; Peng, H.; Hu, Y. Chem. Commun. 2020, 56, 15181. |
| [74] | Hong, J.; Xiao, X.; Liu, H.; Fu, L.; Wang, X.-C.; Zhou, L.; Wang, X.-Y.; Qiu, Z.; Cao, X.-Y.; Narita, A.; Müllen, K.; Hu, Y. Chem. Commun. 2021, 57, 5566. |
| [75] | Xu, Q.; Wang, C.; Zhao, Y.; Zheng, D.; Shao, C.; Guo, W.; Deng, X.; Wang, Y.; Chen, X.; Zhu, J.; Jiang, H. Org. Lett. 2020, 22, 7397. |
| [76] | Xu, Q.; Wang, C.; Zheng, D.; He, J.; Wang, Y.; Chen, X.; Jiang, H. J. Org. Chem. 2021, 86, 13990. |
| [77] | Fujikawa, T.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2016, 138, 3587. |
| [78] | Zhou, F.; Huang, Z.; Huang, Z.; Cheng, R.; Yang, Y.; You, J. Org Lett. 2021, 23, 4559. |
| [79] | Xu, Q.; Wang, C.; Zheng, D.; Wang, Y.; Chen, X.; Sun, D.; Jiang, H. Sci. China Chem. 2021, 64, 590. |
| [80] | Zhu, Y.; Xia, Z.; Cai, Z.; Yuan, Z.; Jiang, N.; Li, T.; Wang, Y.; Guo, X.; Li, Z.; Ma, S.; Zhong, D.; Li, Y.; Wang, J. J. Am. Chem. Soc. 2018, 140, 4222. |
| [81] | Rulíšek, L.; Exner, O.; Cwiklik, L.; Jungwirth, P.; Starý, I.; Pospíšil, L.; Havlas, Z. J. Phys. Chem. C 2007, 111, 14948. |
| [82] | Wang, Y.; Yin, Z.; Zhu, Y.; Gu, J.; Li, Y.; Wang, J. Angew. Chem., nt. Ed. 2019, 58, 587. |
| [83] | Zhu, Y.; Guo, X.; Li, Y.; Wang, J. J. Am. Chem. Soc. 2019, 141, 5511. |
| [84] | Cruz, C. M.; Márquez, I. R.; Castro-Fernández, S.; Cuerva, J. M.; Maçòas, E.; Campaña, A. G. Angew. Chem., nt. Ed. 2019, 58, 8068. |
| [85] | Ma, S.; Gu, J.; Lin, C.; Luo, Z.; Zhu, Y.; Wang, J. J. Am. Chem. Soc. 2020, 142, 16887. |
| [86] | Castro-Fernández, S.; Cruz, C. M.; Mariz, I. F. A.; Márquez, I. R.; Jiménez, V. G.; Palomino-Ruiz, L.; Cuerva, J. M.; Maçòas, E.; Campaña, A. G. Angew. Chem., nt. Ed. 2020, 59, 7139. |
| [87] | Yao, X.; Zheng, W.; Osella, S.; Qiu, Z.; Fu, S.; Schollmeyer, D.; Müller, B.; Beljonne, D.; Bonn, M.; Wang, H. I.; Müllen, K.; Narita, A. J. Am. Chem. Soc. 2021, 143, 5654. |
| [88] | Ma, J.; Fu, Y.; Dmitrieva, E.; Liu, F.; Komber, H.; Hennersdorf, F.; Popov, A. A.; Weigand, J. J.; Liu, J.; Feng, X. Angew. Chem., nt. Ed. 2020, 59, 5637. |
| [89] | Han, Y.; Xue, Z.; Li, G.; Gu, Y.; Ni, Y.; Dong, S.; Chi, C. Angew. Chem., nt. Ed. 2020, 59, 9026. |
| [90] | Qiu, Z.; Asako, S.; Hu, Y.; Ju, C. W.; Liu, T.; Rondin, L.; Schollmeyer, D.; Lauret, J. S.; Müllen, K.; Narita, A. J. Am. Chem. Soc. 2020, 142, 14814. |
| [91] | Shen, C.; Zhang, G.; Ding, Y.; Yang, N.; Gan, F.; Crassous, J.; Qiu, H. Nat. Commun. 2021, 12, 2786. |
/
| 〈 |
|
〉 |