ACS Publications. Most Trusted. Most Cited. Most Read
Novel Open-Cage Fullerenes Having a 12-Membered-Ring Orifice:  Removal of the Organic Addends from the Rim of the Orifice

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2004, 6, 8, 1245-1247
    Letter

    Novel Open-Cage Fullerenes Having a 12-Membered-Ring Orifice:  Removal of the Organic Addends from the Rim of the Orifice
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Chemistry, University of Crete, 71409 Iraklion, Greece, and Department of Chemistry, University of Sussex, Brighton BN1 9QJ, UK
    Other Access OptionsSupporting Information (1)

    Organic Letters

    Cite this: Org. Lett. 2004, 6, 8, 1245–1247
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol049843b
    Published March 13, 2004
    Copyright © 2004 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Two novel open-cage fullerene derivatives bearing a 12-membered-ring orifice on the fullerene cage have been isolated. Removal of the N-MEM protective group leads to the first open-cage [60]fullerene derivative without organic addends on the rim of the orifice.

    Copyright © 2004 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    †

     University of Crete.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    ‡

     University of Sussex.

    Supporting Information Available

    Click to copy section linkSection link copied!

    Detailed experimental procedures, NMR, FT-IR, and UV−VIS spectra. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 36 publications.

    1. Yoshifumi Hashikawa, Yasujiro Murata. Cobalt-Functionalized Open-[60]Fullerenes. Organometallics 2024, 43 (3) , 227-232. https://doi.org/10.1021/acs.organomet.3c00484
    2. Yoshifumi Hashikawa, Michihisa Murata, Atsushi Wakamiya, and Yasujiro Murata . Synthesis of Open-Cage Ketolactam Derivatives of Fullerene C60 Encapsulating a Hydrogen Molecule. Organic Letters 2014, 16 (11) , 2970-2973. https://doi.org/10.1021/ol501113y
    3. Yuming Yu, Xiang Xie, Tong Zhang, Shuming Liu, Yuanhua Shao, Liangbing Gan, and Yuliang Li . Synthesis of 18-Membered Open-Cage Fullerenes through Controlled Stepwise Fullerene Skeleton Bond Cleavage Processes and Substituent-Mediated Tuning of the Redox Potential of Open-Cage Fullerenes. The Journal of Organic Chemistry 2011, 76 (24) , 10148-10153. https://doi.org/10.1021/jo202014q
    4. M. Jalilur Rahman, Jun Yamakawa, Aoi Matsumoto, Hideo Enozawa, Tohru Nishinaga, Kenji Kamada and Masahiko Iyoda. Synthesis of Nonaphenylenes and Dodecaphenylenes Using Electron-Transfer Oxidation of Lipshutz Cuprates and Formation of Nanostructural Materials from Hexadodecyloxynonaphenylene. The Journal of Organic Chemistry 2008, 73 (14) , 5542-5548. https://doi.org/10.1021/jo800787u
    5. Zuo Xiao,, Jiayao Yao,, Dazhi Yang,, Fudong Wang,, Shaohua Huang,, Liangbing Gan,, Zhenshan Jia,, Zhongping Jiang,, Xiaobing Yang,, Bo Zheng,, Gu Yuan,, Shiwei Zhang, and, Zheming Wang. Synthesis of [59]Fullerenones through Peroxide-Mediated Stepwise Cleavage of Fullerene Skeleton Bonds and X-ray Structures of Their Water-Encapsulated Open-Cage Complexes. Journal of the American Chemical Society 2007, 129 (51) , 16149-16162. https://doi.org/10.1021/ja0763798
    6. G. Klupp,, F. Borondics,, É. Kováts,, Á. Pekker,, G. Bényei,, I. Jalsovszky,, R. Hackl,, S. Pekker, and, K. Kamarás. Vibrational Spectra of C60·C8H8 and C70·C8H8 in the Rotor-stator and Polymer Phases. The Journal of Physical Chemistry B 2007, 111 (43) , 12375-12382. https://doi.org/10.1021/jp075204h
    7. Carlo Thilgen and, François Diederich. Structural Aspects of Fullerene ChemistryA Journey through Fullerene Chirality. Chemical Reviews 2006, 106 (12) , 5049-5135. https://doi.org/10.1021/cr0505371
    8. Takeshi Kawase and, Hiroyuki Kurata. Ball-, Bowl-, and Belt-Shaped Conjugated Systems and Their Complexing Abilities:  Exploration of the Concave−Convex π−π Interaction. Chemical Reviews 2006, 106 (12) , 5250-5273. https://doi.org/10.1021/cr0509657
    9. Michihisa Murata,, Yasujiro Murata, and, Koichi Komatsu. Synthesis and Properties of Endohedral C60 Encapsulating Molecular Hydrogen. Journal of the American Chemical Society 2006, 128 (24) , 8024-8033. https://doi.org/10.1021/ja061857k
    10. Sho-ichi Iwamatsu,, Shizuaki Murata,, Yukihiro Andoh,, Masayuki Minoura,, Kaoru Kobayashi,, Naomi Mizorogi, and, Shigeru Nagase. Open-Cage Fullerene Derivatives Suitable for the Encapsulation of a Hydrogen Molecule. The Journal of Organic Chemistry 2005, 70 (12) , 4820-4825. https://doi.org/10.1021/jo050251w
    11. Yoshifumi Hashikawa, Shumpei Sadai, Shu Okamoto, Yasujiro Murata. Near‐Infrared‐Absorbing Chiral Open [60]Fullerenes. Angewandte Chemie 2023, 135 (2) https://doi.org/10.1002/ange.202215380
    12. Yoshifumi Hashikawa, Shumpei Sadai, Shu Okamoto, Yasujiro Murata. Near‐Infrared‐Absorbing Chiral Open [60]Fullerenes. Angewandte Chemie International Edition 2023, 62 (2) https://doi.org/10.1002/anie.202215380
    13. Zhen Liu, Rui Gao, Zeyu Liu, Zongpu Xia, Xueli Liu, Jialin Ming, Xiaoge Wang, Jie Su, Liangbing Gan. Synthesis of Open‐Cage Fullerenes with Pyrrole, Pyrrolone, Pyridinone, Iminofuran, and Pyranone Fragments Embedded on the Rim of the Orifice. European Journal of Organic Chemistry 2021, 2021 (41) , 5694-5701. https://doi.org/10.1002/ejoc.202100908
    14. Yoshifumi Hashikawa, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata. Structural modification of open-cage fullerene C 60 derivatives having a small molecule inside their cavities. Canadian Journal of Chemistry 2017, 95 (3) , 320-328. https://doi.org/10.1139/cjc-2016-0465
    15. Teruhiko Tanaka, Ryuichi Nojiri, Yoshiki Sugiyama, Ryouhei Sawai, Toshikazu Takahashi, Norihisa Fukaya, Jun-Chul Choi, Yoshio Kabe. Regioselective Diels–Alder reaction to open-cage ketolactam derivatives of C 60. Organic & Biomolecular Chemistry 2017, 15 (29) , 6136-6146. https://doi.org/10.1039/C7OB01347G
    16. Chi‐Shian Chen, Wen‐Yann Yeh. An Open‐Cage Fullerene That Mimics the C 60 H 10 (5,5)‐Carbon Nanotube Endcap to Host Acetylene and Hydrogen Cyanide Molecules. Chemistry – A European Journal 2016, 22 (46) , 16425-16428. https://doi.org/10.1002/chem.201604114
    17. Chi‐Shian Chen, Ting‐Shen Kuo, Wen‐Yann Yeh. Encapsulation of Formaldehyde and Hydrogen Cyanide in an Open‐Cage Fullerene. Chemistry – A European Journal 2016, 22 (26) , 8773-8776. https://doi.org/10.1002/chem.201601737
    18. 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
    19. Shuming Liu, Liangbing Gan. Aniline Induced Domino Ring Contraction Process on the Rim of an Open-Cage Fullerene with Carbonyl, Imino and Iactone Moieties. Chinese Journal of Chemistry 2014, 32 (8) , 819-821. https://doi.org/10.1002/cjoc.201400410
    20. Chi‐Shian Chen, Yu‐Fang Lin, Wen‐Yann Yeh. Activation of Open‐Cage Fullerenes with Ruthenium Carbonyl Clusters. Chemistry – A European Journal 2014, 20 (4) , 936-940. https://doi.org/10.1002/chem.201304186
    21. Fa‐Bao Li, Guan‐Wu Wang. Fullerenes. 2013, 1-89. https://doi.org/10.1002/0471238961.0621121220012512.a01.pub2
    22. Jianxin Zhang, Fudong Wang, Nana Xin, Dazhi Yang, Liangbing Gan. Preparation of Ketolactone and Bislactone [60]Fullerene Derivatives and Their Conversion into Open‐Cage Fullerenes with a 12‐ or 15‐Membered Orifice. European Journal of Organic Chemistry 2011, 2011 (27) , 5366-5373. https://doi.org/10.1002/ejoc.201100777
    23. Liangbing Gan, Dazhi Yang, Qianyan Zhang, Huan Huang. Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices. Advanced Materials 2010, 22 (13) , 1498-1507. https://doi.org/10.1002/adma.200903705
    24. Georgios C. Vougioukalakis, Manolis M. Roubelakis, Michael Orfanopoulos. Open-cage fullerenes: towards the construction of nanosized molecular containers. Chem. Soc. Rev. 2010, 39 (2) , 817-844. https://doi.org/10.1039/B913766A
    25. Zuo Xiao, Jiayao Yao, Yuming Yu, Zhenshan Jia, Liangbing Gan. Carving two adjacent holes on [60]fullerene through two consecutive epoxide to diol to dione transformations. Chemical Communications 2010, 46 (44) , 8365. https://doi.org/10.1039/c0cc02750b
    26. Yoshio Kabe, Houjin Hachiya, Tomohisa Saito, Daisuke Shimizu, Masakatsu Ishiwata, Kazuharu Suzuki, Yuko Yakushigawa, Wataru Ando. Diastereoselective syntheses and oxygenation of silyl fulleroids. Journal of Organometallic Chemistry 2009, 694 (13) , 1988-1997. https://doi.org/10.1016/j.jorganchem.2009.01.046
    27. Houjin Hachiya, Yoshio Kabe. Production of a 15-membered Ring Orifice in Open-cage Fullerenes by Double Photooxygenation of Azafulleroid. Chemistry Letters 2009, 38 (4) , 372-373. https://doi.org/10.1246/cl.2009.372
    28. Masahiko Iyoda. . Advanced Synthesis & Catalysis 2009, 984. https://doi.org/10.1002/adsc.200900048
    29. Zhongping Jiang, Yan Zhang, Liangbing Gan, Zheming Wang. Preparation of fullerenol, fullerenone, and aminofullerene derivatives through selective cleavage of fullerene C–H, C–C, C–N, and C–O bonds in fullerene-mixed peroxide derivatives. Tetrahedron 2008, 64 (50) , 11394-11403. https://doi.org/10.1016/j.tet.2008.08.053
    30. Norbert Hoffmann. Photochemical Reactions as Key Steps in Organic Synthesis. Chemical Reviews 2008, 108 (3) , 1052-1103. https://doi.org/10.1021/cr0680336
    31. Xiaobing Yang, Liangbing Gan, Zheming Wang. Controlled regio- and chemoselective addition of isothiocyanate to the dione moiety of a cage-opened fullerene-mixed peroxide derivative. Chemical Communications 2008, 106 (17) , 1980. https://doi.org/10.1039/b800722e
    32. Manolis M. Roubelakis, Georgios C. Vougioukalakis, Michael Orfanopoulos. Open-Cage Fullerene Derivatives Having 11-, 12-, and 13-Membered-Ring Orifices:  Chemical Transformations of the Organic Addends on the Rim of the Orifice. The Journal of Organic Chemistry 2007, 72 (17) , 6526-6533. https://doi.org/10.1021/jo070796l
    33. Koichi Komatsu, Yasujiro Murata. A New Route to an Endohedral Fullerene by Way of σ-Framework Transformations. Chemistry Letters 2005, 34 (7) , 886-891. https://doi.org/10.1246/cl.2005.886
    34. P. R. Birkett. 21  Fullerenes. Annual Reports Section "A" (Inorganic Chemistry) 2005, 101 , 429. https://doi.org/10.1039/b414979n
    35. Sho-ichi Iwamatsu, Shizuaki Murata. H2O@open-cage fullerene C60: control of the encapsulation property and the first mass spectroscopic identification. Tetrahedron Letters 2004, 45 (34) , 6391-6394. https://doi.org/10.1016/j.tetlet.2004.07.008
    36. Georgios C. Vougioukalakis, Kosmas Prassides, Josep M. Campanera, Malcolm I. Heggie, Michael Orfanopoulos. Open-Cage Fullerene Derivatives with 15-Membered-Ring Orifices. The Journal of Organic Chemistry 2004, 69 (13) , 4524-4526. https://doi.org/10.1021/jo049842x
    Download PDF
    Go to Organic Letters
    Get e-Alerts
    Get e-Alerts

    Organic Letters

    Cite this: Org. Lett. 2004, 6, 8, 1245–1247
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol049843b
    Published March 13, 2004
    Copyright © 2004 American Chemical Society
    Request reuse permissions

    Article Views

    438

    Altmetric

    -

    Citations

    36
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.