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 journalArticlepeer-review

48 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 languageEnglish (US)
Pages (from-to)12410-12413
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number32
DOIs
StatePublished - Aug 17 2011
Externally publishedYes

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