Chinese Journal of Organic Chemistry >
Progress in Metal-Organic Supramolecular System Based on Subcomponent Self-Assembly
Received date: 2020-12-19
Revised date: 2021-01-12
Online published: 2021-02-22
Supported by
National Natural Science Foundation of China(21801062)
Subcomponent self-assembly is the most convenient and effective method to construct diverse metal-organic supramolecular architectures. It has become a powerful research tool for assembling rapidly together through simple building blocks via formation of covalent bonds around metal ions. This review focuses on the introduction of several metal-organic supramolecular systems based on subcomponent self-assembly, including helical structures, tetrahedral structures, hexahedral structures and octahedral structures. The unique chemical microenvironment which is derived from the internal cavities of these supramolecular structures can be used for guest recognition, protection, catalysis and extraction. Finally, the future development of this field is prospected.
Changxing Ji , Guangxia Wang , Hua Wang . Progress in Metal-Organic Supramolecular System Based on Subcomponent Self-Assembly[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2261 -2279 . DOI: 10.6023/cjoc202012030
| [1] | Philp, D.; Stoddart, J. F. Angew. Chem.,Int. Ed. 1996, 35,1154. |
| [2] | Northrop, B. H.; Zheng, Y. R.; Chi, K. W.; Stang, P. J. Acc. Chem. Res. 2009, 42,1554. |
| [3] | Chakrabarty, R.; Mukherjee, P. S.; Stang, P. J. Chem. Rev. 2011, 111,6810. |
| [4] | Cook, T. R.; Stang, P. J. Chem. Rev. 2015, 115,7001. |
| [5] | Datta, S.; Saha, M. L.; Stang, P. J. Acc. Chem. Res. 2018, 51,2047. |
| [6] | Sun, Y.; Chen, C.; Stang, P. J. Acc. Chem. Res. 2019, 52,802. |
| [7] | Sun, Y.; Chen, C.; Liu, J.; Stang, P. J. Chem. Soc. Rev. 2020, 49,3889. |
| [8] | Pedersen, C. J. J. Am. Chem. Soc. 1967, 89,7017. |
| [9] | Pedersen, C. J. Angew. Chem., Int. Ed. 1988, 27,1021. |
| [10] | Cram, D. J. Angew. Chem.,Int. Ed. 1988, 27,1009. |
| [11] | Lehn, J. M. Angew. Chem., Int. Ed. 1988, 27,89. |
| [12] | Lehn, J. M. Science 1993, 260,1762. |
| [13] | Robert, F. Science 2005, 309,95. |
| [14] | Pei, Q.; Ding, A. X. Prog. Chem. 2019, 31,258(in Chinese). |
| [14] | (裴强, 丁爱祥, 化学进展, 2019, 31,258.) |
| [15] | Pei, Q.; Ding, A. X.; Wang, J. W.; Xu, W. H.; Xu G. J. Xinyang Norm. Univ. (Nat. Sci. Ed.) 2020, 33,503(in Chinese). |
| [15] | (裴强, 丁爱祥, 王家文, 徐文豪, 徐果, 信阳师范学院学报(自然科学版), 2020, 33,503.) |
| [16] | Yu, J.; Chen, X.; Yang, Y.; Zhao, X.; Chen, X.; Jing, T.; Zhou, Y.; Xu, J.; Zhang, Y.; Cheng, Y. J. Mater. Chem. B 2020, 8,3058. |
| [17] | Xiao, T. X.; Zhou, L.; Wei, X. Y.; Li, Z. Y.; Sun, X. Q. Chin. J. Org. Chem. 2020, 40,944(in Chinese). |
| [17] | (肖唐鑫, 周玲, 魏小艳, 李正义, 孙小强, 有机化学, 2020, 40,944.) |
| [18] | Sun, W. D.; Ye, L.; Liu, J.; Zheng, L.; Guo, W. C.; Han, S. Q.; Shao, C. Y.; Jiang, H. Chin. J. Org. Chem. 2019, 39,2867(in Chinese). |
| [18] | (孙卫东, 叶琳, 刘佳, 郑璐, 郭文彩, 韩森凯, 邵成园, 江华, 有机化学, 2019, 39,2867.) |
| [19] | Wang, Y. Z.; Wu, A. X. Chin. J. Org. Chem. 2008, 28,997(in Chinese). |
| [19] | (王宇宙, 吴安心, 有机化学, 2008, 28,997.) |
| [20] | Wang, J. L.; Jiao, Y.; Yang B. S. Chin. J. Inorg. Chem. 2014, 30,411(in Chinese). |
| [20] | (王璟琳, 焦勇, 杨斌盛, 无机化学学报, 2014, 30,411.) |
| [21] | Li, M.; Zajaczkowski, W.; Velpula, G.; Jänsch, D.; Graf, R.; Marszalek, T.; Parekh, S. H.; Zagranyarski, Y.; Mali, K.; Wagner, M.; De Feyter, S.; Li, C.; Müllen, K.; Pisula, W. Chem. Sci. 2020, 11,4960. |
| [22] | Nitschke, J. R. Acc. Chem. Res. 2007, 40,103. |
| [23] | Hutin, M.; Schultz, D.; Nitschke, J. R. CHIMIA 2008, 62,198. |
| [24] | Nitschke, J. R., Ed.: Pignataro, In Tomorrow's Chemistry Today: Concepts in Nanoscience, Organic Materials and Environmental, Chemistry, Wiley VCH, Weinheim, 2008, pp.3~29. |
| [25] | Castilla, A. M.; Ramsay, W. J.; Nitschke, J. R. Acc. Chem. Res. 2014, 47,2063. |
| [26] | Zhang, D.; Ronson, T. K.; Nitschke, J. R. Acc. Chem. Res. 2018, 51,2423. |
| [27] | Huang, G. B.; Jiang, W. Prog. Chem. 2015, 27,744(in Chinese). |
| [27] | (黄国保, 蒋伟, 化学进展, 2015, 27,744.) |
| [28] | Lehn, J. M.; Eliseev, A. V. Science 2001, 291,2331. |
| [29] | Xu, S.; Giuseppone, N. J. Am. Chem. Soc. 2008, 130,1826. |
| [30] | Liu, Y. B. Master's Thesis, Lanzhou University, Lanzhou, 2019(in Chinese). |
| [30] | (刘彦博, 硕士论文, 兰州大学, 兰州, 2019.) |
| [31] | Hubin, T. J.; Busch, D. H. Coord. Chem. Rev. 2000, 200,5. |
| [32] | Vance, A. L.; Alcock, N. W.; Heppert, J. A.; Busch, D. H. Inorg. Chem. 1998, 37,6912. |
| [33] | Nitschke, J. R. Angew. Chem., Int. Ed. 2004, 43,3073. |
| [34] | GodoyAlcántar, C.; Yatsimirsky, A. K.; Lehn, J. M. J. Phys. Org. Chem. 2005, 18,979. |
| [35] | Santini, J.; John, T.; Richards, A. C.; Scheidt, R.; Cima, M. J.; Langer, R. Angew. Chem., Int. Ed. 2000, 39,2396. |
| [36] | Severin, K. Chem. Eur. J. 2004, 10,2565. |
| [37] | Albrecht, M. Chem. Rev. 2001, 101,3457. |
| [38] | Jiang, H.; Li, Q. L.; Wang, G. X. Chin. J. Org. Chem. 2018, 38,1065(in Chinese). |
| [38] | (江华, 李巧连, 王光霞, 有机化学, 2018, 38,1065.) |
| [39] | Guarracino, D. A.; Riordan, J. A.; Barreto, G. M.; Oldfield, A. L.; Kouba, C. M.; Agrinsoni, D. Chem. Rev. 2019, 119,9915. |
| [40] | Zhang, D. W.; Wang, H.; Li, Z. T. Prog. Chem. 2020, 32,1665(in Chinese). |
| [40] | (张丹维, 王辉, 黎占亭, 化学进展, 2020, 32,1665.) |
| [41] | Zhang, S.; Liu, X.; Li, C. L.; Li, L.; Song, J. S.; Shi, J. W.; Morton, M.; Rajca, S.; Rajca, A.; Wang, H. J. Am. Chem. Soc. 2016, 138,10002. |
| [42] | Tian, Y.; Wang, G. X.; Ma, Z. Y.; Xu, L.; Wang, H. Chem. Eur. J. 2018, 24,15993. |
| [43] | Li, Q. L.; Huang, F.; Fan, Y. X.; Wang, Y. L.; Li, J. F.; He, Y. J.; Jiang, H. Eur. J. Inorg. Chem. 2014, 2014 3235. |
| [44] | Lehn, J. M.; Rigault, A.; Siegel, J.; Harrowfield, J.; Chevrier, B.; Moras, D. Proc. Natl. Acad. Sci. 1987, 84,2565. |
| [45] | Hutin, M.; Frantz, R.; Nitschke, J. R. Chem.-Eur. J. 2006, 12,4077. |
| [46] | Ziessel, R.; Harriman, A.; Suffert, J.; Youinou, M. T.; De Cian, A.; Fischer, J. Angew. Chem.,Int. Ed. 1997, 36,2509. |
| [47] | Ameerunisha, S.; Schneider, J.; Meyer, T.; Henkel, G.; Zacharias, P. S.; Bill, E. Chem. Commun. 2000, 21,2155. |
| [48] | Schultz, D.; Nitschke, J. R. Proc. Natl. Acad. Sci. 2005, 102,11191. |
| [49] | Domer, J.; Slootweg, J. C.; Hupka, F.; Lammertsma, K.; Hahn, F. E. Angew. Chem., Int. Ed. 2010, 49,6430. |
| [50] | Zhang, F. L.; Tian, L.; Qin, L. F.; Chen, J. Q.; Li, Z.; Ren, X.; Gu, Z. G. Polyhedron 2016, 104,9. |
| [51] | Chinnaraja, E.; Arunachalam, R.; Pillai, R. S.; Peuronen, A.; Rissanen, K.; Subramanian, P. S. Appl. Organomet. Chem. 2020, 34,e5666. |
| [52] | Sorensen, A.; Castilla, A. M.; Ronson, T. K.; Pittelkow, M.; Nitschke, J. R. Angew. Chem., Int. Ed. 2013, 52,11273. |
| [53] | Scherer, M.; Caulder, D. L.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 1999, 38,1587. |
| [54] | Hiraoka, S.; Yi, T.; Shiro, M.; Shionoya, M. J. Am. Chem. Soc. 2002, 124,14510. |
| [55] | Custelcean, R.; Bonnesen, P. V.; Duncan, N. C.; Zhang, X.; Watson, L. A.; Van Berkel, G.; Parson, W. B.; Hay, B. P. J. Am. Chem. Soc. 2012, 134,8525. |
| [56] | Han, M.; Hey, J.; Kawamura, W.; Stalke, D.; Shionoya, M.; Clever, G. H. Inorg. Chem. 2012, 51,9574. |
| [57] | Riddell, I. A.; Smulders, M. M.; Clegg, J. K.; Hristova, Y. R.; Breiner, B.; Thoburn, J. D.; Nitschke, J. R. Nat. Chem. 2012, 4,751. |
| [58] | Nitschke, J. R.; Schultz, D.; Bernardinelli, G.; Gérard, D. J. Am. Chem. Soc. 2004, 126,16538. |
| [59] | Hutin, M.; Schalley, C. A.; Bernardinelli, G.; Nitschke, J. R. Chem.- Eur. J. 2006, 12,4069. |
| [60] | Schultz, D.; Nitschke, J. R. J. Am. Chem. Soc. 2006, 128,9887. |
| [61] | Hristova, Y. R.; Smulders, M. M. J.; Clegg, J. K.; Breiner, B.; Nitschke, J. R. Chem. Sci. 2011, 2,638. |
| [62] | Meng, W.; Ronson, T. K.; Clegg, J. K.; Nitschke, J. R. Angew. Chem., Int. Ed. 2013, 52,1017. |
| [63] | Mirtschin, S.; SlabonTurski, A.; Scopelliti, R.; Velders, A. H.; Severin, K.. J. Am. Chem. Soc. 2010, 132,14004. |
| [64] | Struch, N.; Frömbgen, C.; Schnakenburg, G.; Lützen, A. Eur. J. Org. Chem. 2017, 2017 4984. |
| [65] | Fazio, E.; Haynes, C. J. E.; de la Torre, G.; Nitschke, J. R.; Torres, T. Chem. Commun. 2018, 54,2651. |
| [66] | Fu, X. H.; Wu, W. Y.; Jiang, P.; Han, Z. Y.; Wan, R. Quim. Nova 2018, 41,528. |
| [67] | Zhang, J. H.; Wang, H. P.; Zhang, L. Y.; Wei, S. C.; Wei, Z. W.; Pan, M.; Su, C. Y. Chem. Sci. 2020, 11,8885. |
| [68] | Kobatake, S.; Imao, S.; Yamashiro, Y.; Terakawa, Y. Tetrahedron Lett. 2011, 52,1905. |
| [69] | Estrader, M.; Salinas Uber, J.; Barrios, L. A.; Garcia, J.; LloydWilliams, P.; Roubeau, O.; Teat, S. J.; Aromí, G. Angew. Chem.,Int. Ed. 2017, 56,15622. |
| [70] | Kashihara, R.; Morimoto, M.; Ito, S.; Miyasaka, H.; Irie, M. J. Am. Chem. Soc. 2017, 139,16498. |
| [71] | Fu, Q. T.; Yan, X.; Zhang, X. Y.; He, Y.; Zhang, W. D.; Liu, Y.; Li, Y.; Gu, Z. G. Dalton. Trans. 2020, 49,12145. |
| [72] | Cram, D. J.; Cram, J. M. Science 1974, 183,803. |
| [73] | Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1978, 11,8. |
| [74] | Breiner, B.; Nitschke, J. R., Eds.: Gale, P. A.; Steed, J. W. In Supramolecular Chemistry, John Wiley & Sons, Ltd., New Jersey, 2011, pp.1575~1588. |
| [75] | Tominaga, M.; Suzuki, K.; Kawano, M.; Kusukawa, T.; Ozeki, T.; Sakamoto, S.; Yamaguchi, K.; Fujita, M. Angew. Chem.,Int. Ed. 2004, 43,5621. |
| [76] | Sun, Q. F.; Iwasa, J.; Ogawa, D.; Ishido, Y.; Sato, S.; Ozeki, T.; Sei, Y.; Yamaguchi, K.; Fujita, M. Science 2010, 328,1144. |
| [77] | Mal, P.; Schultz, D.; Beyeh, K.; Rissanen, K.; Nitschke, J. R. Angew. Chem., Int. Ed. 2008, 47,8297. |
| [78] | Riddell, I. A.; Smulders, M. M.; Clegg, J. K.; Nitschke, J. R. Chem. Commun. 2011, 47,457. |
| [79] | Lindley, A. A.; McCulloch, A. J. Fluorine Chem. 2005, 126,1457. |
| [80] | Mal, P.; Breiner, B.; Rissanen, K.; Nitschke, J. R. Science 2009, 324,1697. |
| [81] | Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312,251. |
| [82] | Murase, T.; Horiuchi, S.; Fujita, M. J. Am. Chem. Soc. 2010, 132,2866. |
| [83] | Smulders, M. M. J.; Nitschke, J. R.. Chem. Sci. 2012, 3,785. |
| [84] | Salles, A. G., Jr.; Zarra, S.; Turner, R. M.; Nitschke, J. R.. J. Am. Chem. Soc. 2013, 135,19143. |
| [85] | Gollnick, K.; Griesbeck, A. Tetrahedron 1985, 41,2057. |
| [86] | Bolliger, J. L.; Belenguer, A. M.; Nitschke, J. R.. Angew. Chem., Int. Ed. 2013, 52,7958. |
| [87] | Meng, W.; Clegg, J. K.; Thoburn, J. D.; Nitschke, J. R. J. Am. Chem. Soc. 2011, 133,13652. |
| [88] | Grommet, A. B.; Nitschke, J. R. J. Am. Chem. Soc. 2017, 139,2176. |
| [89] | Bolliger, J. L.; Ronson, T. K.; Ogawa, M.; Nitschke, J. R. J. Am. Chem. Soc. 2014, 136,14545. |
| [90] | Grommet, A. B.; Bolliger, J. L.; Browne, C.; Nitschke, J. R. Angew. Chem., Int. Ed. 2015, 54,15100. |
| [91] | Freire, M. G.; Santos, L. M. N. B. F.; Fernandes, A. M.; Coutinho, J. A. P.; Marrucho, I. M. Fluid Phase Equilib. 2007, 261,449. |
| [92] | Ranke, J.; Othman, A.; Fan, P.; Muller, A. Int. J. Mol. Sci. 2009, 10,1271. |
| [93] | Grommet, A. B.; Hoffman, J. B.; Percastegui, E. G.; Mosquera, J.; Howe, D. J.; Bolliger, J. L.; Nitschke, J. R. J. Am. Chem. Soc. 2018, 140,14770. |
| [94] | Jimenez, A.; Bilbeisi, R. A.; Ronson, T. K.; Zarra, S.; Woodhead, C.; Nitschke, J. R. Angew. Chem., Int. Ed. 2014, 53,4556. |
| [95] | Chen, S.; Chen, L. J.; Yang, H. B.; Tian, H.; Zhu, W. J. Am. Chem. Soc. 2012, 134,13596. |
| [96] | Han, M.; Michel, R.; He, B.; Chen, Y. S.; Stalke, D.; John, M.; Clever, G. H. Angew. Chem., Int. Ed. 2013, 52,1319. |
| [97] | Oldknow, S.; Martir, D. R.; Pritchard, V. E.; Blitz, M. A.; Fishwick, C. W. G.; ZysmanColman, E.; Hardie, M. J. Chem. Sci. 2018, 9,8150. |
| [98] | Baxter, P. N.; Khoury, R. G.; Lehn, J. M.; Baum, G.; Fenske, D. Chem.-Eur. J. 2000, 6,4140. |
| [99] | Heo, J.; Jeon, Y. M.; Mirkin, C. A. J. Am. Chem. Soc. 2007, 129,7712. |
| [100] | Kilbas, B.; Mirtschin, S.; Scopelliti, R.; Severin, K. Chem. Sci. 2012, 3,701. |
| [101] | Gidron, O.; Jirasek, M.; Trapp, N.; Ebert, M. O.; Zhang, X.; Diederich, F. J. Am. Chem. Soc. 2015, 137,12502. |
| [102] | Ibukuro, F.; Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1998, 120,8561. |
| [103] | Tu, Y.; Peng, F.; Sui, X.; Men, Y.; White, P. B.; van Hest, J. C. M.; Wilson, D. A. Nat. Chem. 2017, 9,480. |
| [104] | Venkata, Rao, K.; Miyajima, D.; Nihonyanagi, A.; Aida, T. Nat. Chem. 2017, 9,1133. |
| [105] | Yao, Z. Q.; Xu, J.; Zou, B.; Hu, Z.; Wang, K.; Yuan, Y. J.; Chen, Y. P.; Feng, R.; Xiong, J. B.; Hao, J.; Bu, X. H. Angew. Chem.,Int. Ed. 2019, 58,5614. |
| [106] | Zhang, D.; Ronson, T. K.; Guryel, S.; Thoburn, J. D.; Wales, D. J.; Nitschke, J. R. J. Am. Chem. Soc. 2019, 141,14534. |
| [107] | Nguyen, B. T.; Grommet, A. B.; Tron, A.; Georges, M. C. A.; Nitschke, J. R. Adv. Mater. 2020, 32,1907241. |
| [108] | Yao, W.; Wang, H.; Cui, G.; Li, Z.; Zhu, A.; Zhang, S.; Wang, J. Angew. Chem., Int. Ed. 2016, 55,7934. |
| [109] | Yi, S.; Brega, V.; Captain, B.; Kaifer, A. E. Chem. Commun. 2012, 48,10295. |
| [110] | Frischmann, P. D.; Kunz, V.; Stepanenko, V.; Wurthner, F. Chem.- Eur. J. 2015, 21,2766. |
| [111] | Frischmann, P. D.; Kunz, V.; Wurthner, F. Angew. Chem.,Int. Ed. 2015, 54,7285. |
| [112] | Xi, S. F.; Bao, L. Y.; Lin, J. G.; Liu, Q. Z.; Qiu, L.; Zhang, F. L.; Wang, Y. X.; Ding, Z. D.; Li, K.; Gu, Z. G. Chem. Commun. 2016, 52,10261. |
| [113] | Bao, L. Y.; Hao, S. J.; Xi, S. F.; Yan, X.; Zhang, H. X.; Shen, R.; Gu, Z. G. Chem. Commun.2018, 54, 8725. |
| [114] | Meyer-Luehmann, M.; Spires-Jones, T. L.; Prada, C.; Garcia-Alloza, M.; Calignon, A. D.; Rozkalne, A.; Koenigsknecht-Talboo, J.; Holtzman, D. M.; Bacskai, B. J.; Hyman, B. T. Nature 2008, 451,720. |
| [115] | Li, M.; Xu, C.; Ren, J.; Wang, E.; Qu, X. Chem. Commun. 2013, 49,11394. |
| [116] | Kotler, S. A.; Walsh, P.; Brender, J. R.; Ramamoorthy, A. Chem. Soc. Rev. 2014, 43,6692. |
| [117] | Lendel, C.; Bjerring, M.; Dubnovitsky, A.; Kelly, R. T.; Filippov, A.; Antzutkin, O. N.; Nielsen, N. C.; Hard, T. Angew. Chem., Int. Ed. 2014, 53,12756. |
| [118] | Selkoe, D. J.; Hardy, J. EMBO Mol. Med. 2016, 8,595. |
| [119] | Yang, L.; Jing, X.; An, B.; He, C.; Yang, Y.; Duan, C. Chem. Sci. 2018, 9,1050. |
| [120] | Hardy, M.; Engeser, M.; Lützen, A. Beilstein J. Org. Chem. 2020, 16,2701. |
| [121] | Ronson, T. K.; Meng, W.; Nitschke, J. R. J. Am. Chem. Soc. 2017, 139,9698. |
| [122] | Meng, W.; Breiner, B.; Rissanen, K.; Thoburn, J. D.; Clegg, J. K.; Nitschke, J. R. Angew. Chem., Int. Ed. 2011, 50,3479. |
| [123] | Struch, N.; Bannwarth, C.; Ronson, T. K.; Lorenz, Y.; Mienert, B.; Wagner, N.; Engeser, M.; Bill, E.; Puttreddy, R.; Rissanen, K.; Beck, J.; Grimme, S.; Nitschke, J. R.; Lützen, A. Angew. Chem.,Int. Ed. 2017, 56,4930. |
| [124] | Adams, G. B.; O"Keeffe, M.; Ruoff, R. S. J. Phys. Chem. 1994, 98,9465. |
| [125] | Mecozzi, S.; Rebek, J. Jr. Chem.-Eur. J. 1998, 4,1016. |
| [126] | Mosquera, J.; Szyszko, B.; Ho, S. K.; Nitschke, J. R. Nat. Commun. 2017, 8,14882. |
| [127] | Sham, K. C.; Yiu, S. M.; Kwong, H. L. Inorg. Chem. 2013, 52,5648. |
| [128] | Rizzuto, F. J.; Wu, W. Y.; Ronson, T. K.; Nitschke, J. R. Angew. Chem.,Int. Ed. 2016, 55,7958. |
| [129] | Bilbeisi, R. A.; Ronson, T. K.; Nitschke, J. R. Angew. Chem., Int. Ed. 2013, 52,9027. |
| [130] | Rizzuto, F. J.; Nitschke, J. R. Nat. Chem. 2017, 9,903. |
| [131] | Browne, C.; Ronson, T. K.; Nitschke, J. R. Angew. Chem., nt. Ed. 2014, 53,10701. |
| [132] | Ronson, T. K.; Wang, Y.; Baldridge, K.; Siegel, J. S.; Nitschke, J. R. J. Am. Chem. Soc. 2020, 142,10267. |
| [133] | Meng, W.; Clegg, J. K.; Nitschke, J. R. Angew. Chem., nt. Ed. 2012, 51,1881. |
| [134] | Wood, C. S.; Ronson, T. K.; McConnell, A. J.; Roberts, D. A.; Nitschke, J. R. Chem. Sci. 2016, 7,1702. |
/
| 〈 |
|
〉 |
