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Expansion of Orifices of Open C60 Derivatives and Formation of an Open C59S Derivative by Reaction with Sulfur

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Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan, and JST, PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
[email protected]
†Kyoto University.
‡JST, PRESTO.
Cite this: Org. Lett. 2013, 15, 11, 2750–2753
Publication Date (Web):May 15, 2013
https://doi.org/10.1021/ol401083c
Copyright © 2013 American Chemical Society
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Abstract

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The reaction of a tetraketo-open-cage C60 derivative with elemental sulfur in the presence of tetrakis(dimethylamino)ethylene afforded novel open C60 derivatives containing sulfur atom(s) in the rim of the orifice and the first example of an open C59S derivative. The single crystal X-ray analyses clearly determined these structures and demonstrated that a water molecule was encapsulated inside the cages. The orifice sizes and electronic properties of these fullerene derivatives were revealed.

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Experimental procedure and spectroscopic data for all new compounds, calculated geometries, and cif files for compounds 3, 4, and 5. This material is available free of charge via the Internet at http://pubs.acs.org.

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This article is cited by 36 publications.

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  2. Sheng-Li Wu, Zong-Jun Li, Xiang Gao. Dithiolation of [70]Fullerene with Aliphatic Primary Thiols in the Presence of n-Butylamine via Aerobic Oxidation Reaction. The Journal of Organic Chemistry 2019, 84 (6) , 3045-3054. https://doi.org/10.1021/acs.joc.8b02462
  3. Rui Zhang, Tsukasa Futagoishi, Michihisa Murata, Atsushi Wakamiya, and Yasujiro Murata . Synthesis and Structure of an Open-Cage Thiafullerene C69S: Reactivity Differences of an Open-Cage C70 Tetraketone Relative to Its C60 Analogue. Journal of the American Chemical Society 2014, 136 (23) , 8193-8196. https://doi.org/10.1021/ja504054s
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  5. Yoshifumi Hashikawa, Shota Hasegawa, Yasujiro Murata. Precise Fixation of an NO Molecule inside Carbon Nanopores: A Long‐Range Electron–Nuclear Interaction. Angewandte Chemie International Edition 2021, 60 (6) , 2866-2870. https://doi.org/10.1002/anie.202012538
  6. Yoshifumi Hashikawa, Shu Okamoto, Yasujiro Murata. Nonclassical Abramov Products Formed on Orifices of Cage‐Opened C 60 Derivatives. Chemistry – A European Journal 2021, 111 https://doi.org/10.1002/chem.202004035
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  16. Sally Bloodworth, John Gräsvik, Shamim Alom, Karel Kouřil, Stuart J. Elliott, Neil J. Wells, Anthony J. Horsewill, Salvatore Mamone, Mónica Jiménez-Ruiz, Stéphane Rols, Urmas Nagel, Toomas Rõõm, Malcolm H. Levitt, Richard J. Whitby. Synthesis and Properties of Open Fullerenes Encapsulating Ammonia and Methane. ChemPhysChem 2018, 19 (3) , 266-276. https://doi.org/10.1002/cphc.201701212
  17. Rui Zhang, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata. Synthesis and Structure of an Open-cage C 69 O Derivative. Chemistry Letters 2017, 46 (4) , 543-546. https://doi.org/10.1246/cl.161178
  18. Tsukasa Futagoishi, Tomoko Aharen, Tatsuhisa Kato, Azusa Kato, Toshiyuki Ihara, Tomofumi Tada, Michihisa Murata, Atsushi Wakamiya, Hiroshi Kageyama, Yoshihiko Kanemitsu, Yasujiro Murata. A Stable, Soluble, and Crystalline Supramolecular System with a Triplet Ground State. Angewandte Chemie 2017, 129 (15) , 4325-4329. https://doi.org/10.1002/ange.201701212
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  20. Tsukasa Futagoishi, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata. Encapsulation and Dynamic Behavior of Methanol and Formaldehyde inside Open-Cage C 60 Derivatives. Angewandte Chemie 2017, 129 (10) , 2802-2806. https://doi.org/10.1002/ange.201611903
  21. Tsukasa Futagoishi, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata. Encapsulation and Dynamic Behavior of Methanol and Formaldehyde inside Open-Cage C 60 Derivatives. Angewandte Chemie International Edition 2017, 56 (10) , 2758-2762. https://doi.org/10.1002/anie.201611903
  22. Kapil S. Pandit, Uday V. Desai, Prakash P. Wadgaonkar, Kisan M. Kodam. Sulfamic acid-catalyzed, environmentally benign synthesis of bis-tetronic acids at ambient temperature. Research on Chemical Intermediates 2017, 43 (1) , 141-152. https://doi.org/10.1007/s11164-016-2611-y
  23. T. Matsuno, S. Sato, H. Isobe. Curved π-Receptors. 2017,,, 311-328. https://doi.org/10.1016/B978-0-12-409547-2.12518-1
  24. . Comprehensive Supramolecular Chemistry II. 2017,,https://doi.org/
  25. Tsukasa Futagoishi, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata. Unprecedented photochemical rearrangement of an open-cage C 60 derivative. Chemical Communications 2017, 53 (10) , 1712-1714. https://doi.org/10.1039/C6CC10103H
  26. Teruhiko Tanaka, Ryuichi Nojiri, Yoshiki Sugiyama, Ryouhei Sawai, Toshikazu Takahashi, Norihisa Fukaya, Jun-Chul Choi, Yoshio Kabe. . Organic & Biomolecular Chemistry 2017,,, 6136. https://doi.org/10.1039/C7OB01347G
  27. Yanbang Li, Gaihong Zhang, Dian Wang, Beidi Xu, Dan Xu, Ning Lou, Liangbing Gan. Fullerene-Based Macro-Heterocycle Prepared through Selective Incorporation of Three N and Two O Atoms into C 60. Angewandte Chemie 2016, 128 (47) , 14810-14814. https://doi.org/10.1002/ange.201606856
  28. Yanbang Li, Gaihong Zhang, Dian Wang, Beidi Xu, Dan Xu, Ning Lou, Liangbing Gan. Fullerene-Based Macro-Heterocycle Prepared through Selective Incorporation of Three N and Two O Atoms into C 60. Angewandte Chemie International Edition 2016, 55 (47) , 14590-14594. https://doi.org/10.1002/anie.201606856
  29. Tsukasa Futagoishi, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata. Trapping N 2 and CO 2 on the Sub-Nano Scale in the Confined Internal Spaces of Open-Cage C 60 Derivatives: Isolation and Structural Characterization of the Host-Guest Complexes. Angewandte Chemie 2015, 127 (49) , 15004-15007. https://doi.org/10.1002/ange.201507785
  30. Tsukasa Futagoishi, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata. Trapping N 2 and CO 2 on the Sub-Nano Scale in the Confined Internal Spaces of Open-Cage C 60 Derivatives: Isolation and Structural Characterization of the Host-Guest Complexes. Angewandte Chemie International Edition 2015, 54 (49) , 14791-14794. https://doi.org/10.1002/anie.201507785
  31. Yasujiro Murata. Open-Cage Fullerene Derivatives: Synthesis, Reactions, and Encapsulation of a Small Molecule. 2015,,, 117-131. https://doi.org/10.1007/978-4-431-55357-1_8
  32. , , , , . Chemical Science of π-Electron Systems. 2015,,https://doi.org/10.1007/978-4-431-55357-1
  33. Andrea Krachmalnicoff, Richard Bounds, Salvatore Mamone, Malcolm H. Levitt, Marina Carravetta, Richard J. Whitby. Synthesis and characterisation of an open-cage fullerene encapsulating hydrogen fluoride. Chemical Communications 2015, 51 (24) , 4993-4996. https://doi.org/10.1039/C5CC00499C
  34. Andrea Krachmalnicoff, Malcolm H. Levitt, Richard J. Whitby. An optimised scalable synthesis of H 2 [email protected] 60 and a new synthesis of H 2 @C 60. Chem. Commun. 2014, 50 (86) , 13037-13040. https://doi.org/10.1039/C4CC06198E
  35. Lijun Shi, Dazhi Yang, Francesca Colombo, Yuming Yu, Wen‐Xiong Zhang, Liangbing Gan. Punching a Carbon Atom of C 60 into its Own Cavity to Form an Endohedral Complex [email protected] 59 O 6 under Mild Conditions. Chemistry – A European Journal 2013, 19 (49) , 16545-16549. https://doi.org/10.1002/chem.201303501
  36. Lijun Shi, Liangbing Gan. Open-cage fullerenes as tailor-made container for a single water molecule. Journal of Physical Organic Chemistry 2013, 26 (10) , 766-772. https://doi.org/10.1002/poc.3169

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