Detection of methoxylated anions of fullerenes by electrospray ionization mass spectrometry

• 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
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja00075a057

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.