Detection of methoxylated anions of fullerenes by electrospray ionization mass spectrometry

Electrospray ionization mass spectrometry (ESI-MS) has been applied to the study of the reactions of fullerenes in solution. The C[sub 60][sup [minus]] and other anionic species are readily examined directly in 1:1 toluene/methanol by negative ion ESI-MS. Addition of a NaOMe/MeOH solution to C[sub 6...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1993-11, Vol.115 (22), p.10334-10337
Main Authors: Wilson, Stephen R, Wu, Yunhui
Format: Article
Language:English
Subjects:
400102 - Chemical & Spectral Procedures
400201 - Chemical & Physicochemical Properties
ALCOHOLS
ALKYLATED AROMATICS
ANIONS
AROMATICS
CARBON
CHARGED PARTICLES
CHEMICAL REACTIONS
Chemistry
COUPLING
DEUTERIUM COMPOUNDS
ELEMENTS
Exact sciences and technology
FULLERENES
GLYCOLS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
IONS
Mass spectrometry
MASS SPECTROSCOPY
METHANOL
NONMETALS
Organic chemistry
ORGANIC COMPOUNDS
ORGANIC POLYMERS
OXIDATION
POLYETHYLENE GLYCOLS
POLYMERS
Reactivity and mechanisms
SPECTROSCOPY
TOLUENE
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Summary:Electrospray ionization mass spectrometry (ESI-MS) has been applied to the study of the reactions of fullerenes in solution. The C[sub 60][sup [minus]] and other anionic species are readily examined directly in 1:1 toluene/methanol by negative ion ESI-MS. Addition of a NaOMe/MeOH solution to C[sub 60] in toluene leads to formation of C[sub 60][sup [minus]] and C[sub 60](OMe)[sub n][sup [minus]] (n = 1, 3, 5, 7) as major anions as well as a product derived from coupling and oxidation with toluene, C[sub 60]O[sub 2](CH[sub 2]C[sub 6]H[sub 5])[sup [minus]]. The expected isotopic shifts of the peaks in deuteriomethanol or deuteriotoluene confirmed the proposed formulas. Similar experiments on C[sub 70] gave the same types of anions. A crown ether tagged fulleroid was also used for the same reaction, but the ESI-MS study could be done in both positive and negative ion modes. Our results showed that fulleroids do have chemical properties similar to those of fullerenes themselves. 21 refs., 4 figs.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00075a057