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Sidewall Carboxylic Acid Functionalization of Single-Walled Carbon Nanotubes

2003; American Chemical Society; Volume: 125; Issue: 49 Linguagem: Inglês

10.1021/ja037746s

1943-2984

Haiqing Peng, Lawrence B. Alemany, John L. Margrave, Valéry N. Khabashesku,

Fullerene Chemistry and Applications

The reactions of single-walled carbon nanotubes (SWNTs) with succinic or glutaric acid acyl peroxides in o-dichlorobenzene at 80−90 °C resulted in the addition of 2-carboxyethyl or 3-carboxypropyl groups, respectively, to the sidewalls of the SWNT. These acid-functionalized SWNTs were converted to acid chlorides by derivatization with SOCl2 and then to amides with terminal diamines such as ethylenediamine, 4,4'-methylenebis(cyclohexylamine), and diethyltoluenediamine. The acid-functionalized SWNTs and the amide derivatives were characterized by a set of materials characterization methods including attenuated total reflectance (ATR) FTIR, Raman and solid state 13C NMR spectroscopy, transmission electron microscopy (TEM), and thermal gravimetry-mass spectrometry (TG-MS). The degree of SWNT sidewall functionalization with the acid-terminated groups was estimated as 1 in 24 carbons on the basis of TG-MS data. In comparison with the pristine SWNTs, the acid-functionalized SWNTs show an improved solubility in polar solvents, for example, alcohols and water, which enables their processing for incorporation into polymer composite structures as well as for a variety of biomedical applications.