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.
Original language | English (US) |
---|---|
Pages (from-to) | 12410-12413 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 133 |
Issue number | 32 |
DOIs | |
State | Published - Aug 17 2011 |
Externally published | Yes |
Bibliographical note
KAUST Repository Item: Exported on 2020-10-01Acknowledged KAUST grant number(s): KUS-C1-015-21
Acknowledgements: 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).
This publication acknowledges KAUST support, but has no KAUST affiliated authors.
ASJC Scopus subject areas
- General Chemistry
- Biochemistry
- Catalysis
- Colloid and Surface Chemistry