Type
ArticleAuthors
Li, HuapingRisko, Chad
Seo, Jung Hwa
Campbell, Casey
Wu, Guang
Brédas, Jean-Luc
Bazan, Guillermo C.

KAUST Grant Number
KUS-C1-015-21Date
2011-08-17Permanent link to this record
http://hdl.handle.net/10754/598378
Metadata
Show full item recordAbstract
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.Citation
Li 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.Sponsors
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).Publisher
American Chemical Society (ACS)PubMed ID
21761908ae974a485f413a2113503eed53cd6c53
10.1021/ja204974m
Scopus Count
Collections
Publications Acknowledging KAUST SupportRelated articles
- Charge transfer via the dative N-B bond and dihydrogen contacts. Experimental and theoretical electron density studies of small Lewis acid-base adducts.
- Authors: Mebs S, Grabowsky S, Förster D, Kickbusch R, Hartl M, Daemen LL, Morgenroth W, Luger P, Paulus B, Lentz D
- Issue date: 2010 Sep 23
- Dihydrogen activation by frustrated carbene-borane Lewis pairs: an experimental and theoretical study of carbene variation.
- Authors: Kronig S, Theuergarten E, Holschumacher D, Bannenberg T, Daniliuc CG, Jones PG, Tamm M
- Issue date: 2011 Aug 1
- Lewis Acid-Base Adducts of Sc<sub>2</sub>C<sub>2</sub>@C<sub>3v</sub>(8)-C<sub>82</sub>/N-Heterocyclic Carbene: Toward Isomerically Pure Metallofullerene Derivatives.
- Authors: Bao L, Chen M, Shen W, Yang L, Jin P, Lu X
- Issue date: 2017 Dec 18
- Sc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub> -C<sub>80</sub> as a novel Lewis acid to trap abnormal <i>N</i>-heterocyclic carbenes: the unprecedented formation of a singly bonded [6,6,6]-adduct.
- Authors: Chen M, Bao L, Ai M, Shen W, Lu X
- Issue date: 2016 Mar 1
- Divalent carbon(0) chemistry, part 2: Protonation and complexes with main group and transition metal Lewis acids.
- Authors: Tonner R, Frenking G
- Issue date: 2008