Fullerene-carbene Lewis acid-base adducts

Huaping Li; Chad Risko; Jung Hwa Seo; Casey Campbell; Guang Wu; Jean Luc Brédas; Guillermo C. Bazan

doi:10.1021/ja204974m

Fullerene-carbene Lewis acid-base adducts

Huaping Li, Chad Risko, Jung Hwa Seo, Casey Campbell, Guang Wu, Jean Luc Brédas, Guillermo C. Bazan^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

57 Scopus citations

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	https://doi.org/10.1021/ja204974m
State	Published - Aug 17 2011
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged 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

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja204974m

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title = "Fullerene-carbene Lewis acid-base adducts",

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.",

author = "Huaping Li and Chad Risko and Seo, {Jung Hwa} and Casey Campbell and Guang Wu and Br{\'e}das, {Jean Luc} and Bazan, {Guillermo C.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged 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.",

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AU - Li, Huaping

AU - Risko, Chad

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AU - Campbell, Casey

AU - Wu, Guang

AU - Brédas, Jean Luc

AU - Bazan, Guillermo C.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged 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.

PY - 2011/8/17

Y1 - 2011/8/17

N2 - 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.

AB - 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.

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Fullerene-carbene Lewis acid-base adducts

Abstract

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ASJC Scopus subject areas

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