Fullerene in Carbon Nanoring: A Saturn-Like Supramolecular Complex

doi:10.21127/yaoyigc20200018

Abstract

Abstract: Fullerenes have attracted much attention because of their unique electronic structure and spherical cage shape. Specially, fullerenes have been widely used as guest in supramolecular chemistry due to their spherical structures. Recently, the supramolecular complexes of fullerenes and several types of carbon nanorings have been constructed and investigated. The complex of fullerene in carbon nanoring is like a Saturn, and this unique kind of supramolecular complexes will have potential applications in chemical, material and physical fields. In this review, various complexes of fullerene in carbon nanoring and their special properties are described. We hope to expand the application of these supramolecular complexes in various fields.

Key words: fullerene, carbon nanoring, host-guest interaction, supramolecular complex

Jie Zhang, Chunru Wang, and Taishan Wang. Fullerene in Carbon Nanoring: A Saturn-Like Supramolecular Complex[J]. General Chemistry, 2021, 7(2): 200018-200018.

References

[1] Kroto, H. W.; Allaf, A. W.; Balm, S. P. C₆₀: Buckminsterfullerene. Nature 1985, 91, 1213.
[2] Shinohara, H. Endohedral metallofullerenes. Rep. Prog. Phys. 2000, 63, 843.
[3] Sota, S.; Takashi, Y; Hiroyuki, I. Solid-state structures of peapod bearings composed of finite single-wall carbon nanotube and fullerene molecules. Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 8374–8379.
[4] Wu, D.; Cheng, W.; Ban, X. T.; Xia, J. L. Cycloparaphenylenes (CPPs): An Overview of Synthesis, Properties, and Potential Applications. J. Org. Chem. 2018, 7, 2161–2181.
[5] Yuan, K.; Guo, Y. J.; Yang, T.; Dang, J. S.; Zhao, P; Li, Q. Z., Zhao, X. Theoretical insights into the host-guest interactions between [6]cycloparaphenyleneacetylene and its anthracene-containing derivative and fullerene C₇₀. J. Phys. Org. Chem. 2014, 27, 772–782.
[6] Toyota, S.; Tsurumaki, E. Exploration of Nano-Saturns: A Spectacular Sphere-Ring Supramolecular System. Chem.-Eur. J. 2019, 25, 6878–6890.
[7] Evans; Paul, J.; Jasti, R. Molecular Belts. Top. Curr. Chem. 2014, 349, 249–290.
[8] Kawase, T.; Tanaka, K.; Seirai, Y.; Shiono, N.; Oda, M. Complexation of Carbon Nanorings with Fullerenes: Supramolecular Dynamics and Structural Tuning for a Fullerene Sensor. Angew. Chem. Int. Ed. 2003, 115, 5755–5758.
[9] Xu, Y. Z.; Delius, M. V. The Supramolecular Chemistry of Strained Carbon Nanohoops. Angew. Chem. Int. Ed. 2020, 59, 559–573.
[10] Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cyclopara- phenylene: Carbon Nanohoop Structures. J. Am. Chem. Soc. 2008, 130, 17646–17647.
[11] Iwamoto, T.; Watanabe, Y.; Sadahiro, T.; Haino, T.; Yamago, S. Size-selective encapsulation of C₆₀ by [10]cycloparaphenylene: formation of the shortest fullerene-peapod. Angew. Chem. Int. Ed. 2011, 123, 8492–8494.
[12] Yuan, K.; Guo, Y. J.; Zhao, X.; Nature of Noncovalent Interactions in the [n]Cycloparaphenylene⊃C70 (n = 10, 11, and 12) Host-Guest Complexes: A Theoretical Insight into the Shortest C70–Carbon Nanotube Peapod. J. Phys. Chem. C. 2015, 119, 5168–5179.
[13] Xu, Y. Z.; Kaur, R.; Wang, B. Z.; Minameyer, M. B.; Gsanger, S.; Meyer, B.; Drewwllo. T.; Guldi, D. M.; Delius, M. V. Concave- Convex pi-pi Template Approach Enables the Synthesis of [10]Cycloparaphenylene-Fullerene [2]Rotaxanes. J. Am. Chem. Soc. 2018, 140, 13413–13420.
[14] Rio, J.; Beeck, B.; Rotas, G.; Ahles, S.; Jacquemin, D.; Tagmatarchis, N.; Ewels, C.; Wegner, H. A. Electronic Communication between two [10]cycloparaphenylenes and Bis(azafullerene) (C₅₉N)2 Induced by Cooperative Complexation. Angew. Chem. Int. Ed. 2018, 57, 6930–6934.
[15] Huang, Q.; Zhuang, G. L; Jia, H. X.; Qian, M. M.; Cui, S. S.; Yang, S. F.; Du, P. W. Photoconductive Curved-Nanographene/Fullerene Supramolecular Heterojunctions. Angew. Chem. Int. Ed. 2019, 58, 6244–6249.
[16] Iyoda, M.; Shimizu, H. Multifunctional π-expanded oligothiophene macrocycles. Chem. Soc. Rev. 2015, 44, 6411–6424.
[17] Kigure, S.; Haruka, Q.; Hisanori, S.; Susumu, O. Nano-Saturn: Energetics of the Inclusion Process of C₆₀ into Cyclohexabi- phenylene. J. Phys. Chem. C. 2015, 119, 8931–8936.
[18] Yamamoto, Y.; Tsurumaki, E.; Wakamatsu, K.; Toyota, S. Nano-Saturn: Experimental Evidence ofComplex Formation of an Anthracene Cyclic Ring with C60. Angew. Chem. Int. Ed. 2018, 57, 8199–8202.
[19] Toyota, S.; Yamamoto, Y.; Wakamatsu, K.; Tsurumaki, E.; Muñoz- Castro, A. Nano-Saturn with an Ellipsoidal Body: Anthracene Macrocyclic Ring–C₇₀ Complex. Bull. Chem. Soc. Jpn. 2019, 92, 1721–1728.
[20] Nakanishi, Y.; Omachi, H., Matsuura, S.; Miyata, Y.; Kitaura, R.; Segawa, Y.; Itami, K.; Shinohara, H. Size-Selective Complexation and Extraction of Endohedral Metallofullerenes with Cyclo- paraphenylene. Angew. Chem. Int. Ed. 2014, 53, 3102–3106.
[21] Iwamoto, T.; Slanina, Z.; Mizorogi, N.; Guo, J. D.; Akasaka, T.; Nagase, S.; Takaya, H.; Yasuda, N.; Kato, T.; Yamago, S. Partial Charge Transfer in the Shortest Possible Metallofullerene Peapod, La@C82⊂[11]Cycloparaphenylene. Chem.-Eur. J. 2014, 20, 1–8.
[22] Ueno, H.; Nishihara, T.; Segawa, Y.; Itami, K. Cycloparaphenylene- based ionic donor-acceptor supramolecule: isolation and characterization of Li(+)@C₆₀ subset[10]CPP. Angew. Chem. Int. Ed. 2015, 54, 3707–3711.
[23] Leonhardt, E. J.; Jasti, R. Emerging applications of carbon nanohoops. Nat. Rev. Chem. 2019, 3, 672–686.
[24] Zhang, J.; Zhao, C.; Meng, H. B.; Nie, M. Z.; Li, Q.; Xiang, J. F.; Zhang, Z. X.; Wang, C. R.; Wang, T. S. Size-selective encapsulation of metallofullerenes by [12]Cycloparaphenylene and dissociation using metal-organic framework. Carbon 2020, 161, 694–701.
[25] Zhao, C.; Meng, H. B.; Nie, M. Z.; Wang, X.; Cai, Z. F.; Chen, T.; Wang, D.; Wang, C. R.; Wang, T. S. Supramolecular Complexes of C80-Based Metallofullerenes with [12]Cycloparaphenylene Nanoring and Altered Property in a Confined Space. J. Phys. Chem. C 2019, 123, 12514–12520.
[26] Zhao, C.; Meng, H.; Nie, M.; Huang, Q.; Du, P.; Wang, C.; Wang, T. Chem. Commun. 2019, 55, 11511–11514.