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dc.contributor.authorLi, Huaping
dc.contributor.authorRisko, Chad
dc.contributor.authorSeo, Jung Hwa
dc.contributor.authorCampbell, Casey
dc.contributor.authorWu, Guang
dc.contributor.authorBrédas, Jean-Luc
dc.contributor.authorBazan, Guillermo C.
dc.date.accessioned2016-02-25T13:19:42Z
dc.date.available2016-02-25T13:19:42Z
dc.date.issued2011-08-17
dc.identifier.citationLi 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.
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.pmid21761908
dc.identifier.doi10.1021/ja204974m
dc.identifier.urihttp://hdl.handle.net/10754/598378
dc.description.abstractThe 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.
dc.description.sponsorshipThe 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).
dc.publisherAmerican Chemical Society (ACS)
dc.titleFullerene–Carbene Lewis Acid–Base Adducts
dc.typeArticle
dc.identifier.journalJournal of the American Chemical Society
dc.contributor.institutionUniversity of California, Santa Barbara, Santa Barbara, United States
dc.contributor.institutionGeorgia Institute of Technology, Atlanta, United States
dc.contributor.institutionDong-A University, Busan, South Korea
kaust.grant.numberKUS-C1-015-21
kaust.grant.fundedcenterCenter for Advanced Molecular Photovoltaics (CAMP)


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