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Impact of Surface Functionalization on Bacterial Cytotoxicity of Single-Walled Carbon Nanotubes

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Department of Chemical and Environmental Engineering, Yale University, New Haven, Connecticut 06520-8286, United States
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States
§ School of Forestry and Environmental Studies, Yale University, New Haven, Connecticut 06520, United States
*Phone: (203) 432-9703; fax: (203) 432-4837; e-mail: [email protected]
Cite this: Environ. Sci. Technol. 2012, 46, 11, 6297–6305
Publication Date (Web):April 19, 2012
Copyright © 2012 American Chemical Society

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    The addition of surface functional groups to single-walled carbon nanotubes (SWNTs) is realized as an opportunity to achieve enhanced functionality in the intended application. At the same time, several functionalized SWNTs (fSWNTs), compared to SWNTs, have been shown to exhibit decreased cytotoxicity. Therefore, this unique class of emerging nanomaterials offers the potential enhancement of SWNT applications and potentially simultaneous reduction of their negative human health and environmental impacts depending on the specific functionalization. Here, the percent cell viability loss of Escherichia coli K12 resulting from the interaction with nine fSWNTs, n-propylamine, phenylhydrazine, hydroxyl, phenydicarboxy, phenyl, sulfonic acid, n-butyl, diphenylcyclopropyl, and hydrazine SWNT, is presented. The functional groups range in molecular size, chemical composition, and physicochemical properties. While physiochemical characteristics of the fSWNTs did not correlate, either singularly or in combination, with the observed trend in cell viability, results from combined light scattering techniques (both dynamic and static) elucidate that the percent loss of cell viability can be correlated to fSWNT aggregate size distribution, or dispersity, as well as morphology. Specifically, when the aggregate size polydispersity, quantified as the width of the distribution curve, and the aggregate compactness, quantified by the fractal dimension, are taken together, we find that highly compact and narrowly distributed aggregate size are characteristics of fSWNTs that result in reduced cytotoxicity. The results presented here suggest that surface functionalization has an indirect effect on the bacterial cytotoxicity of SWNTs through the impact on aggregation state, both dispersity and morphology.

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    Supporting Information includes further details on novel aspects of the hydrazine and diphenylcyclopropyl SWNT functionalization syntheses, the cytotoxicity assay, including representative fluorescent images, the proposed azo coupling byproduct (Figure S6), a list of QikProp descriptors, percent functionalization calculations, and statistical analysis. Additional characterization data including NMR data for diphenylcyclopropyl, n-propylamine, phenylhydrazine, phenyl, and butyl SWNT (Figure S1–S5), QikProp output data of six descriptors for fSWNTs (Table S1), Raman spectra (Figure S7), percent mass loss curves from TGA (Figure S8), tabulated burn off temperatures from DTG curves (Table S1), representative TEM images (Figure S9), tabulated pKa values of the functional groups and proposed dominant species (Table S2), electrophoretic mobilities in 0.9% NaCl (Figure S10), I/Io vs q plots for determining Df (Figure S11), tabulated Df for all fSWNTs (Table S3) and cytotoxicity and aggregate size distributions of ball milled samples (Figure S12). This material is available free of charge via the Internet at

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