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

56 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. © 2011 American Chemical Society.

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.

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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. {\textcopyright} 2011 American Chemical Society.",

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

AU - Seo, Jung Hwa

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. © 2011 American Chemical Society.

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. © 2011 American Chemical Society.

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EP - 12413

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -

Fullerene–Carbene Lewis Acid–Base Adducts

Abstract

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