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Sidewall Carboxylic Acid Functionalization of Single-Walled Carbon Nanotubes
Abstract
The reactions of single-walled carbon nanotubes (SWNTs) with succinic or glutaric acid acyl peroxides in o-dichlorobenzene at 80-90 degrees 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 SOCl(2) 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 (13)C 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.
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Citations
Cited by
Fan, X., Peng, W., Li, Y., Li, X., Wang, S., Zhang, G., & Zhang, F. (2008) · Advanced Materials · doi:10.1002/adma.200801306 · Cited by 1,772
The biocompatibility of carbon nanotubes
Smart, S. K., Cassady, A. I., Lu, G. Q., & Martin, D. J. (2006) · Carbon · doi:10.1016/j.carbon.2005.10.011 · Cited by 1,011
Tang, T., Jiang, W.-J., Niu, S., Liu, N., Luo, H., Chen, Y.-Y., Jin, S.-F., Gao, F., Wan, L.-J., & Hu, J.-S. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b03507 · Cited by 880
Molecular Electronic Junctions
McCreery, R. L. (2004) · Chemistry of Materials · doi:10.1021/cm049517q · Cited by 555
Chae, H. G., Sreekumar, T. V., Uchida, T., & Kumar, S. (2005) · Polymer · doi:10.1016/j.polymer.2005.08.092 · Cited by 271
Metadata
- Authors
- Peng, H., Alemany, L. B., Margrave, J. L., & Khabashesku, V. N.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-11-15
- Volume
- 125
- Issue
- 49
- Pages
- 15174-15182
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2089122317
- Cited by
- 562
- References
- 0
- FWCI
- 14.62
- Type
- journal article
- Language
- en
- Open access
- closed
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- Peng, H., Alemany, L. B., Margrave, J. L., & Khabashesku, V. N. (2003). Sidewall Carboxylic Acid Functionalization of Single-Walled Carbon Nanotubes. Journal of the American Chemical Society. https://doi.org/10.1021/ja037746s
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