ACS Publications. Most Trusted. Most Cited. Most Read
From Planar to Cage in 15 Easy Steps: Resolving the C60H21F9– → C60– Transformation by Ion Mobility Mass Spectrometry

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2016, 138, 35, 11254-11263
    Article

    From Planar to Cage in 15 Easy Steps: Resolving the C60H21F9– → C60– Transformation by Ion Mobility Mass Spectrometry
    Click to copy article linkArticle link copied!

    View Author Information
    † Institute of Physical Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 2, 76131 Karlsruhe, Germany
    ‡ Institute of Nanotechnology, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
    § Institut für Organische Chemie, University Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
    *[email protected]
    *[email protected]
    Other Access OptionsSupporting Information (1)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2016, 138, 35, 11254–11263
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.6b06205
    Published August 8, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    A combination of mass spectrometry, collision-induced dissociation, ion mobility mass spectrometry (IM-MS), and density functional theory (DFT) has been used to study the evolution of anionic species generated by laser-desorption of the near-planar, fluorinated polycyclic aromatic hydrocarbon (PAH), C60H21F9 (s). The dominant decay process for isolated, thermally activated C60H21F9– species comprises a sequence of multiple regioselective cyclodehydrofluorination and cyclodehydrogenation reactions (eliminating HF and H2, respectively, while forming additional pentagons and/or hexagons). The DFT calculations allow us to set narrow bounds on the structures of the resulting fragment ions by fitting structural models to experimentally determined collision cross sections. These show that the transformation of the precursor anion proceeds via a series of intermediate structures characterized by increasing curvature, ultimately leading to the closed-shell fullerene cage C60– as preprogrammed by the precursor structure.

    Copyright © 2016 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.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.6b06205.

    • Additional figures including mass spectra, contour maps of anion signal versus arrival time and mass, and structures, and experimental parameters (PDF)

    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 16 publications.

    1. Dominik Lungerich, Helen Hoelzel, Koji Harano, Norbert Jux, Konstantin Yu. Amsharov, Eiichi Nakamura. A Singular Molecule-to-Molecule Transformation on Video: The Bottom-Up Synthesis of Fullerene C60 from Truxene Derivative C60H30. ACS Nano 2021, 15 (8) , 12804-12814. https://doi.org/10.1021/acsnano.1c02222
    2. Ruth Dorel, Antonio M. Echavarren. From Palladium to Gold Catalysis for the Synthesis of Crushed Fullerenes and Acenes. Accounts of Chemical Research 2019, 52 (7) , 1812-1823. https://doi.org/10.1021/acs.accounts.9b00227
    3. Younes Valadbeigi, Vahideh Ilbeigi, Bartosz Michalczuk, Martin Sabo, Stefan Matejcik. Study of Atmospheric Pressure Chemical Ionization Mechanism in Corona Discharge Ion Source with and without NH3 Dopant by Ion Mobility Spectrometry combined with Mass Spectrometry: A Theoretical and Experimental Study. The Journal of Physical Chemistry A 2019, 123 (1) , 313-322. https://doi.org/10.1021/acs.jpca.8b11417
    4. Jonathan Cremers, Renée Haver, Michel Rickhaus, Juliane Q. Gong, Ludovic Favereau, Martin D. Peeks, Tim D. W. Claridge, Laura M. Herz, Harry L. Anderson. Template-Directed Synthesis of a Conjugated Zinc Porphyrin Nanoball. Journal of the American Chemical Society 2018, 140 (16) , 5352-5355. https://doi.org/10.1021/jacs.8b02552
    5. Papri Chakraborty, Abhijit Nag, Ganesan Paramasivam, Ganapati Natarajan, Thalappil Pradeep. Fullerene-Functionalized Monolayer-Protected Silver Clusters: [Ag29(BDT)12(C60)n]3– (n = 1–9). ACS Nano 2018, 12 (3) , 2415-2425. https://doi.org/10.1021/acsnano.7b07759
    6. Lawrence T. Scott . Exotic Chemistry and Rational Organic Syntheses at 1000 °C. The Journal of Organic Chemistry 2016, 81 (23) , 11535-11547. https://doi.org/10.1021/acs.joc.6b02113
    7. Xiu Huang, Huihui Liu, Dawei Lu, Yue Lin, Jingfu Liu, Qian Liu, Zongxiu Nie, Guibin Jiang. Mass spectrometry for multi-dimensional characterization of natural and synthetic materials at the nanoscale. Chemical Society Reviews 2021, 50 (8) , 5243-5280. https://doi.org/10.1039/D0CS00714E
    8. Dominik Lungerich, Jakob Felix Hitzenberger, Michael Ruppel, Tibor Döpper, Matthias Witt, Ivana Ivanović‐Burmazović, Andreas Görling, Norbert Jux, Thomas Drewello. Gas‐Phase Transformation of Fluorinated Benzoporphyrins to Porphyrin‐Embedded Conical Nanocarbons. Chemistry – A European Journal 2020, 26 (53) , 12180-12187. https://doi.org/10.1002/chem.202002638
    9. Jonathan Cremers. The Template-Directed Synthesis of a Fully Conjugated 14-Porphyrin Nanoball. 2020, 151-221. https://doi.org/10.1007/978-3-030-39101-0_5
    10. Papri Chakraborty, Thalappil Pradeep. The emerging interface of mass spectrometry with materials. NPG Asia Materials 2019, 11 (1) https://doi.org/10.1038/s41427-019-0149-3
    11. Joerg Tomada, Thomas Dienel, Frank Hampel, Roman Fasel, Konstantin Amsharov. Combinatorial design of molecular seeds for chirality-controlled synthesis of single-walled carbon nanotubes. Nature Communications 2019, 10 (1) https://doi.org/10.1038/s41467-019-11192-y
    12. Ulrike Warzok, Lisa K. Mahnke, Wolfgang Bensch. Soluble Hetero‐Polyoxovanadates and Their Solution Chemistry Analyzed by Electrospray Ionization Mass Spectrometry. Chemistry – A European Journal 2019, 25 (6) , 1405-1419. https://doi.org/10.1002/chem.201803291
    13. Konstantin Amsharov. Rational Synthesis of Fullerenes. 2018https://doi.org/10.5772/intechopen.73251
    14. Joerg Tomada, Konstantin Amsharov. Single-Walled Carbon Nanotube's End-Cap Engineering—Molecular Seeds for Controlled Synthesis of Chirality-Pure SWCNT. 2018https://doi.org/10.1016/B978-0-12-409547-2.14210-6
    15. Marc Mulet-Gas, Laura Abella, Maira R. Cerón, Edison Castro, Alan G. Marshall, Antonio Rodríguez-Fortea, Luis Echegoyen, Josep M. Poblet, Paul W. Dunk. Transformation of doped graphite into cluster-encapsulated fullerene cages. Nature Communications 2017, 8 (1) https://doi.org/10.1038/s41467-017-01295-9
    16. Konstantin Amsharov. Towards Rational Synthesis of Non‐IPR Fullerenes Via Tandem Cyclodehydrofluorination of Fluoroarene‐Based Precursors. physica status solidi (b) 2017, 254 (11) https://doi.org/10.1002/pssb.201700170
    Download PDF
    Go to Journal of the American Chemical Society
    Get e-Alerts
    Get e-Alerts

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2016, 138, 35, 11254–11263
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.6b06205
    Published August 8, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

    Article Views

    1242

    Altmetric

    -

    Citations

    16
    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.