Pillararene-Decorated Single-Walled Carbon Nanotubes
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Control of single-walled carbon nanotube dispersion properties is of substantial interest to the scientific community. In this work, we sought to investigate the effect of a macrocycle, pillararene, on the dispersion properties of a polymer-nanotube complex. Pillararenes are a class of electron-rich macrocyclic hosts capable of forming inclusion complexes with electron-poor guests, such as alkyl nitriles. A hydroxyl-functionalized pillararene derivative was coupled to the alkyl bromide side chains of a polyfluorene, which was then used to coat the surface of single-walled carbon nanotubes. Noncovalent functionalization of carbon nanotubes with the macrocycle-containing conjugated polymer significantly enhanced nanotube solubility, resulting in dark and concentrated nanotube dispersions (600 μg mL-1), as evidenced by UV-vis-NIR spectroscopy and thermogravimetric analysis. Differentiation of semiconducting and metallic single-walled carbon nanotube species was analyzed by a combination of UV-vis-NIR, Raman, and fluorescence spectroscopy. Raman spectroscopy confirmed that the concentrated nanotube dispersion produced by the macrocycle-containing polymer was due to well-exfoliated nanotubes, rather than bundle formation. The polymer-nanotube dispersion was investigated using 1H NMR spectroscopy, and it was found that host-guest chemistry between pillararene and 1,6-dicyanohexane occurred in the presence of the polymer-nanotube complex. Utilizing the host-guest capability of pillararene, the polymer-nanotube complex was incorporated into a supramolecular organogel.
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