Citation: Sun Weidong, Ye Lin, Liu Jia, Zheng Lu, Guo Wencai, Han Senkai, Shao Chengyuan, Jiang Hua. Self-Assembled of Corannulene-Based Molecular Cage with Fullerenes as Template[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2867-2874. doi: 10.6023/cjoc201904042 shu

Self-Assembled of Corannulene-Based Molecular Cage with Fullerenes as Template

Key Laboratory of Theoretical and Computational Photochemistry and Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875

Corresponding author: Jiang Hua, jiangh@bnu.edu.cn
Received Date: 16 April 2019
Revised Date: 8 May 2019
Available Online: 3 October 2019
Fund Project: Project supported by the Major State Basic Research Development Program of China (973 Program, No. 2015CB856502) and the National Natural Science Foundation of China (Nos. 21572023, 21672026)the Major State Basic Research Development Program of China 973 Program, No. 2015CB856502the National Natural Science Foundation of China 21572023the National Natural Science Foundation of China 21672026

Figures(7)

A tetrapyridyl substituted corannulene derivative COPY2 was designed and synthesized. Only in the presence of template molecule C₆₀ or C₇₀, COPY2 and palladium could form 1:1 molecular cage complex C_60/70⊂COPY2-Pd by self-assembly at room temperature and 55℃ respectively. C₆₀ and C₇₀ were used not only as a template for constructing target molecular cages, but also as a stabilizer for molecular cage. When 1.0 equiv. C₇₀ mixed with C₆₀⊂COPY2-Pd or 1.0 equiv. C₆₀ mixed with C₇₀⊂COPY2-Pd, the ratio of complex C₆₀⊂COPY2-Pd to C₇₀⊂COPY2-Pd is 4:1 after the mixtures were heated at 90℃ for 48 h, which is consistent with the ratio of COPY2 and Pd(CH₃CN)₂Cl₂ mixed with C₆₀ and C₇₀ (1:1). Only the complex C₆₀⊂COPY2-Pd was observed when the ratio of C₆₀ to C₇₀ is 2:1. However, even the ratio of C₆₀ to C₇₀ is 1:2, complex C₆₀⊂COPY2-Pd is still the dominant species in the mixture. These results demonstrate that complexing ability of COPY2 with C₆₀ is stronger than that of COPY2 with C₇₀. 4-Dimethylaminopyridine (DMAP) was chosen to dissociate the cage so as to release fullerene and ligand. Therefore, the ligand COPY2 could be used to the enrichment of C₆₀ at room temperature.
- corannulene,
- molecular cage,
- fullerene,
- self-assembly
1. [1]
  Prato, M. J. Mater. Chem. 1997, 7, 1097. doi: 10.1039/a700080d
2. [2]
  Dennler, G.; Scharber, M. C.; Brabec, C. J. Adv. Mater. 2009, 21, 1323. doi: 10.1002/adma.200801283
3. [3]
  Iwasa, Y. Nature 2010, 466, 191. doi: 10.1038/466191a
4. [4]
  Liu, G. F.; Filipovic, M.; Ivanovic-Burmazovic, I.; Beuerle, F.; Witte, P.; Hirsch, A. Angew. Chem., Int. Ed. 2008, 47, 3991. doi: 10.1002/anie.200800008
5. [5]
  Hirsch, A.; Brettreich, M. Fullerenes:Chemistry and Reactions, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2005.
6. [6]
  (a) Shi, H.; Cheng, X.; Lin, Q.; Yao, H.; Zhang, Y.; Wei, T. Chin. J. Org. Chem. 2018, 38, 1718.
  (b) Bai, D.; Zhou, Y.; Lu, J.; Liu, Q.; Chen, Q.; Tao, Z.; Xiao, X. Chin. J. Org. Chem. 2018, 38, 1477.
  (c) Li, W.; Qu, W.; Zhang, H.; Li, X.; Lin, Q.; Yao, H.; Zhang, Y.; Wei, T. Chin. J. Org. Chem. 2017, 37, 2639.
  (d) Yang, L.; Hu, J.; Zeng, W.; Wu, Y.; Li, X.; Zhang, D.; Jin, W. Chin. J. Org. Chem. 2017, 37, 2654.
  (e) Yi, J.; Chen, M.; Xue, S.; Tao, Z. Chin. J. Org. Chem. 2016, 36, 653.
7. [7]
  (a) Garcia-Simon, C.; Costas, M.; Ribas, X. Chem., Soc. Rev. 2016, 45, 40.
  (b) Canevet, D.; Perez, E. M.; Martin, N. Angew. Chem. Int. Ed. 2011, 50, 9248.
  (c) Tashiro, K.; Aida, T. Chem. Soc. Rev. 2007, 36, 189.
8. [8]
  (a) Lu, Y.; Fu, Z. D.; Guo, Q. H.; Wang, M. X. Org. Lett. 2017, 19, 1590.
  (b) Tashiro, K.; Aida, T.; Zheng, J.-Y.; Kinbara, K.; Saigo, K.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 1999, 121, 9477.
9. [9]
  (a) Rizzuto, F. J.; Nitschke, J. R. Nat. Chem. 2017, 9, 903.
  (b) Kishi, N.; Akita, M.; Yoshizawa, M. Angew. Chem., Int. Ed. 2014, 53, 3604.
  (c) Mahata, K.; Frischmann, P. D.; Wurthner, F. J. Am. Chem. Soc. 2013, 135, 15656.
  (d) Meng, W.; Breiner, B.; Rissanen, K.; Thoburn, J. D.; Clegg, J. K.; Nitschke, J. R. Angew. Chem., Int. Ed. 2011, 50, 3479.
  (e) Kishi, N.; Li, Z.; Yoza, K.; Akita, M.; Yoshizawa, M. J. Am. Chem. Soc. 2011, 133, 11438.
10. [10]
  (a) Inokuma, Y.; Arai, T.; Fujita, M. Nat. Chem. 2010, 2, 780.
  (b) Sun, D.; Tham, F. S.; Reed, C. A.; Boyd, P. D. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5088.
11. [11]
  (a) Zhang, C.; Wang, Q.; Long, H.; Zhang, W. J. Am. Chem. Soc. 2011, 133, 20995.
  (b) Yanagisawa, M.; Tashiro, K.; Yamasaki, M.; Aida, T. J. Am. Chem. Soc. 2007, 11912.
  (c) Shoji, Y.; Tashiro, K.; Aida, T. J. Am. Chem. Soc. 2004, 126, 6570.
12. [12]
  (a) Huerta, E.; Metselaar, G. A.; Fragoso, A.; Santos, E.; Bo, C.; de Mendoza, J. Angew. Chem. Int. Ed. 2007, 46, 202.
  (b) Huerta, E.; Cequier, E.; de Mendoza, J. Chem. Commun. 2007, 5016.
  (c) Huerta, E.; Isla, H.; Pérez, E. M.; Bo, C.; Martín, N.; Mendoza, J. D. J. Am. Chem. Soc. 2010, 132, 5351.
  (d) Li, M.-J.; Huang, C.-H.; Lai, C.-C.; Chiu, S.-H. Org. Lett. 2012, 14, 6146.
13. [13]
  (a) Ke, X. S.; Kim, T.; Lynch, V. M.; Kim, D.; Sessler, J. L. J. Am. Chem. Soc. 2017, 139, 13950.
  (b) Ke, X. S.; Kim, T.; Brewster, J. T., 2nd; Lynch, V. M.; Kim, D.; Sessler, J. L. J. Am. Chem. Soc. 2017, 139, 4627.
  (c) Tian, X. H.; Chen, C. F. Chem.-Eur. J. 2010, 16, 8072.
  (d) Haino, T.; Fukunaga, C.; Fukazawa, Y. Org. Lett. 2006, 8, 3545.
  (e) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. 1998, 37, 997.
  (f) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., lnt. Ed. 1997, 36, 259.
  (g) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229.
14. [14]
  (a) Yang, D. C.; Li, M.; Chen, C. F. Chem. Commun. 2017, 53, 9336.
  (b) Yanney, M.; Fronczek, F. R.; Sygula, A. Angew. Chem., Int. Ed. 2015, 54, 11153.
  (c) Alvarez, C. M.; Garcia-Escudero, L. A.; Garcia-Rodriguez, R.; Martin-Alvarez, J. M.; Miguel, D.; Rayon, V. M. Dalton Trans. 2014, 43, 15693.
  (d) Sygula, A.; Fronczek, F. R.; Sygula, R.; Rabideau, P. W.; Olmstead, M. M. J. Am. Chem. Soc. 2007, 129, 3842.
15. [15]
  (a) Davis, C. M.; Lim, J. M.; Larsen, K. R.; Kim, D. S.; Sung, Y. M.; Lyons, D. M.; Lynch, V. M.; Nielsen, K. A.; Jeppesen, J. O.; Kim, D.; Park, J. S.; Sessler, J. L. J. Am. Chem. Soc. 2014, 136, 10410.
  (b) Jurow, M.; Farley, C.; Pabon, C.; Hageman, B.; Dolor, A.; Drain, C. M. Chem. Commun. 2012, 48, 4731.
  (c) Canevet, D.; Gallego, M.; Isla, H.; de Juan, A.; Perez, E. M.; Martin, N. J. Am. Chem. Soc. 2011, 133, 3184.
  (d) Grimm, B.; Santos, J.; Illescas, B. M.; Muñ oz, A.; Guldi, D. M.; Martín, N. J. Am. Chem. Soc. 2010, 132, 17387.
  (e) Isla, H.; Gallego, M.; Pérez, E. M.; Viruela, R.; Ortí, E.; Martín, N. J. Am. Chem. Soc. 2010, 132, 1772.
  (f) Pérez, E. M.; Sánchez, L.; Fernández, G.; Martín, N. J. Am. Chem. Soc. 2006, 128, 7172.
  (g) Komatsu, N. Org. Biomol. Chem. 2003, 1, 204-209.
16. [16]
  (a) Sanchez-Molina, I.; Grimm, B.; Krick Calderon, R. M.; Claessens, C. G.; Guldi, D. M.; Torres, T. J. Am. Chem. Soc. 2013, 135, 10503.
  (b) Shimizu, S.; Nakano, S.; Hosoya, T.; Kobayashi, N. Chem. Commun. 2011, 47, 316.
17. [17]
  Becker, H.; Javahery, G.; Petrie, S.; Cheng, P. C.; Schwarz, H.; Scott, L. T.; Bohme, D. K. J. Am. Chem. Soc. 1993, 115, 11636. doi: 10.1021/ja00077a088
18. [18]
  Nestoros, E.; Stuparu, M. C. Chem. Commun. 2018, 54, 6503. doi: 10.1039/C8CC02179A
19. [19]
  Mizyed, S.; Georghiou, P. E.; Bancu, M.; Cuadra, B.; Rai, A. K.; Cheng, P.; Scott, L. T. J. Am. Chem. Soc. 2001, 123, 12770. doi: 10.1021/ja016761z
20. [20]
  Dawe, L. N.; AlHujran, T. A.; Tran, H. A.; Mercer, J. I.; Jackson, E. A.; Scott, L. T.; Georghiou, P. E. Chem. Commun. 2012, 48, 5563. doi: 10.1039/c2cc30652b
21. [21]
  Abeyratne Kuragama, P. L.; Fronczek, F. R.; Sygula, A. Org. Lett. 2015, 17, 5292. doi: 10.1021/acs.orglett.5b02666
22. [22]
  Yanney, M.; Sygula, A. Tetrahedron Lett. 2013, 54, 2604. doi: 10.1016/j.tetlet.2013.03.009
23. [23]
  Alvarez, C. M.; Aullon, G.; Barbero, H.; Garcia-Escudero, L. A.; Martinez-Perez, C.; Martin-Alvarez, J. M.; Miguel, D. Org. Lett. 2015, 17, 2578. doi: 10.1021/acs.orglett.5b01161
24. [24]
  Alvarez, C. M.; Barbero, H.; Ferrero, S.; Miguel, D. J. Org. Chem. 2016, 81, 6081. doi: 10.1021/acs.joc.6b00454
25. [25]
  (a) Huang, F.; Wang, G.; Ma, L.; Wang, Y.; Chen, X.; Che, Y.; Jiang, H. J. Org. Chem. 2017, 82, 12106.
  (b) Yu, C.; Ma, L.; He, J.; Xiang, J.; Deng, X.; Wang, Y.; Chen, X.; Jiang, H. J. Am. Chem. Soc. 2016, 138, 15849.
  (c) Wang, G.; Xiao, H.; He, J.; Xiang, J.; Wang, Y.; Chen, X.; Che, Y.; Jiang, H. J. Org. Chem. 2016, 81, 3364.
  (d) Li, Q.; Huang, F.; Fan, Y.; Wang, Y.; Li, J.; He, Y.; Jiang, H. Eur. J. Inorg. Chem. 2014, 2014, 3235.
26. [26]
  (a) Li, M.; Chen, L.-J.; Cai, Y.; Luo, Q.; Li, W.; Yang, H.-B.; Tian, H.; Zhu, W.-H. Chem 2019, 5, 634.
  (b) Zheng, W.; Wang, W.; Jiang, S. T.; Yang, G.; Li, Z.; Wang, X. Q.; Yin, G. Q.; Zhang, Y.; Tan, H.; Li, X.; Ding, H.; Chen, G.; Yang, H. B. J. Am. Chem. Soc. 2019, 141, 583.
  (c) Gao, W.-X.; Fan, Q.-J.; Lin, Y.-J.; Jin, G.-X. Chin. J. Chem. 2018, 36, 594.
  (d) Zhou, J.; Zhang, Y.; Yu, G.; Crawley, M. R.; Fulong, C. R. P.; Friedman, A. E.; Sengupta, S.; Sun, J.; Li, Q.; Huang, F.; Cook, T. R. J. Am. Chem. Soc. 2018, 140, 7730.
  (e) Liu, C. L.; Zhang, R. L.; Lin, C. S.; Zhou, L. P.; Cai, L. X.; Kong, J. T.; Yang, S. Q.; Han, K. L.; Sun, Q. F. J. Am. Chem. Soc. 2017, 139, 12474.
27. [27]
  Jiang, H.; Li, Q.; Wang, G. Chin. J. Org. Chem. 2018, 38, 1065. doi: 10.6023/cjoc201711013
28. [28]
  Huang, F.; Ma, L.; Che, Y.; Jiang, H.; Chen, X.; Wang, Y. J. Org. Chem. 2018, 83, 733. doi: 10.1021/acs.joc.7b02709
29. [29]
  Sun, W.; Wang, Y.; Ma, L.; Zheng, L.; Fang, W.; Chen, X.; Jiang, H. J. Org. Chem. 2018, 83, 14667. doi: 10.1021/acs.joc.8b02674
30. [30]
  (a) Fellows, W. B.; Rice, A. M.; Williams, D. E.; Dolgopolova, E. A.; Vannucci, A. K.; Pellechia, P. J.; Smith, M. D.; Krause, J. A.; Shustova, N. B. Angew. Chem., Int. Ed. 2016, 55, 2195.
  (b) Butterfield, A. M.; Gilomen, B.; Siegel, J. S. Org. Process Res. Dev. 2012, 16, 664.
31. [31]
  (a) Tashiro, S.; Tominaga, M.; Kusukawa, T.; Kawano, M.; Sakamoto, S.; Yamaguchi, K.; Fujita, M. Angew. Chem., Int. Ed. 2003, 42, 3267.
  (b) Tominaga, M.; Tashiro, S.; Aoyagi, M.; Fujita, M. Chem. Commun. 2002, 2038.
32. [32]
  Schmittel, M.; He, B.; Mal, P. Org. Lett. 2008, 2513.
33. [33]
  Garcia-Simon, C.; Garcia-Borras, M.; Gomez, L.; Parella, T.; Osuna, S.; Juanhuix, J.; Imaz, I.; Maspoch, D.; Costas, M.; Ribas, X. Nat. Commun. 2014, 5, 5557. doi: 10.1038/ncomms6557
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