Fullerene-carbene Lewis acid-base adducts |
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Authors: | Li Huaping Risko Chad Seo Jung Hwa Campbell Casey Wu Guang Brédas Jean-Luc Bazan Guillermo C |
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Institution: | Center for Polymers and Organic Solids, Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States. |
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Abstract: | The reaction between a bulky N-heterocylic carbene (NHC) and C(60) 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 C(60) 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 C(60). 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. |
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