• Login
    View Item 
    •   Home
    • Office of Sponsored Research (OSR)
    • KAUST Funded Research
    • Publications Acknowledging KAUST Support
    • View Item
    •   Home
    • Office of Sponsored Research (OSR)
    • KAUST Funded Research
    • Publications Acknowledging KAUST Support
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

    All of KAUSTCommunitiesIssue DateSubmit DateThis CollectionIssue DateSubmit Date

    My Account

    Login

    Quick Links

    Open Access PolicyORCID LibguidePlumX LibguideSubmit an Item

    Statistics

    Display statistics

    Fullerene–Carbene Lewis Acid–Base Adducts

    • CSV
    • RefMan
    • EndNote
    • BibTex
    • RefWorks
    Type
    Article
    Authors
    Li, Huaping
    Risko, Chad
    Seo, Jung Hwa
    Campbell, Casey
    Wu, Guang
    Brédas, Jean-Luc
    Bazan, Guillermo C. cc
    KAUST Grant Number
    KUS-C1-015-21
    Date
    2011-08-17
    Permanent link to this record
    http://hdl.handle.net/10754/598378
    
    Metadata
    Show full item record
    Abstract
    The reaction between a bulky N-heterocylic carbene (NHC) and C60 leads to the formation of a thermally stable zwitterionic Lewis acid-base adduct that is connected via a C-C single bond. Low-energy absorption bands with weak oscillator strengths similar to those of n-doped fullerenes were observed for the product, consistent with a net transfer of electron density to the C60 core. Corroborating information was obtained using UV photoelectron spectroscopy, which revealed that the adduct has an ionization potential ∼1.5 eV lower than that of C60. Density functional theory calculations showed that the C-C bond is polarized, with a total charge of +0.84e located on the NHC framework and -0.84e delocalized on the C 60 cage. The combination of reactivity, characterization, and theoretical studies demonstrates that fullerenes can behave as Lewis acids that react with C-based Lewis bases and that the overall process describes n-doping via C-C bond formation. © 2011 American Chemical Society.
    Citation
    Li H, Risko C, Seo JH, Campbell C, Wu G, et al. (2011) Fullerene–Carbene Lewis Acid–Base Adducts. Journal of the American Chemical Society 133: 12410–12413. Available: http://dx.doi.org/10.1021/ja204974m.
    Sponsors
    The research at UCSB was supported by the National Science Foundation (DMR-1035480) and the Department of Energy through the Center of Energy Efficient Materials. The work at Georgia Tech was partly supported by the STC Program of the National Science Foundation (DMR-012967) and by the Center for Advanced Molecular Photovoltaics (CAMP) through Award KUS-C1-015-21 from King Abdullah University of Science and Technology (KAUST).
    Publisher
    American Chemical Society (ACS)
    Journal
    Journal of the American Chemical Society
    DOI
    10.1021/ja204974m
    PubMed ID
    21761908
    ae974a485f413a2113503eed53cd6c53
    10.1021/ja204974m
    Scopus Count
    Collections
    Publications Acknowledging KAUST Support

    entitlement

    Related articles

    • Charge transfer via the dative N-B bond and dihydrogen contacts. Experimental and theoretical electron density studies of small Lewis acid-base adducts.
    • Authors: Mebs S, Grabowsky S, Förster D, Kickbusch R, Hartl M, Daemen LL, Morgenroth W, Luger P, Paulus B, Lentz D
    • Issue date: 2010 Sep 23
    • Dihydrogen activation by frustrated carbene-borane Lewis pairs: an experimental and theoretical study of carbene variation.
    • Authors: Kronig S, Theuergarten E, Holschumacher D, Bannenberg T, Daniliuc CG, Jones PG, Tamm M
    • Issue date: 2011 Aug 1
    • Lewis Acid-Base Adducts of Sc<sub>2</sub>C<sub>2</sub>@C<sub>3v</sub>(8)-C<sub>82</sub>/N-Heterocyclic Carbene: Toward Isomerically Pure Metallofullerene Derivatives.
    • Authors: Bao L, Chen M, Shen W, Yang L, Jin P, Lu X
    • Issue date: 2017 Dec 18
    • Sc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub> -C<sub>80</sub> as a novel Lewis acid to trap abnormal <i>N</i>-heterocyclic carbenes: the unprecedented formation of a singly bonded [6,6,6]-adduct.
    • Authors: Chen M, Bao L, Ai M, Shen W, Lu X
    • Issue date: 2016 Mar 1
    • Divalent carbon(0) chemistry, part 2: Protonation and complexes with main group and transition metal Lewis acids.
    • Authors: Tonner R, Frenking G
    • Issue date: 2008
    DSpace software copyright © 2002-2021  DuraSpace
    Quick Guide | Contact Us | Send Feedback
    Open Repository is a service hosted by 
    Atmire NV
     

    Export search results

    The export option will allow you to export the current search results of the entered query to a file. Different formats are available for download. To export the items, click on the button corresponding with the preferred download format.

    By default, clicking on the export buttons will result in a download of the allowed maximum amount of items. For anonymous users the allowed maximum amount is 50 search results.

    To select a subset of the search results, click "Selective Export" button and make a selection of the items you want to export. The amount of items that can be exported at once is similarly restricted as the full export.

    After making a selection, click one of the export format buttons. The amount of items that will be exported is indicated in the bubble next to export format.