Supramolecular functionalization of single-walled carbon nanotubes with triply fused porphyrin dimers: A study of structure-property relationships

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DOIResolve DOI: http://doi.org/10.1021/cm2004648
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TypeArticle
Journal titleChemistry of Materials
ISSN0897-4756
Volume23
Issue13
Pages31883194; # of pages: 7
SubjectBathochromic shift; Bulky substituents; Functionalizations; Long alkyl chains; Nanotube bundles; Nanotube surface; Nanotube walls; Porphyrin dimers; Prolonged solution; Single-walled carbon; Soret bands; Structure property relationships; Tert-butyl group; Triply fused porphyrin dimer; UV-vis spectroscopy; Bearings (structural); Dimers; Porphyrins; Positive ions; Raman spectroscopy; Solubility; Supramolecular chemistry; Surface defects; Transmission electron microscopy; Ultraviolet spectroscopy; Single-walled carbon nanotubes (SWCN)
AbstractA triply fused porphyrin dimer bearing long alkyl chains for enhanced solubility was prepared and investigated for its ability to supramolecularly functionalize single-walled carbon nanotubes. It was found that this porphyrin dimer indeed binds strongly to the nanotube surface, allowing the removal of excess unbound porphyrin from solution without diminishing nanotube solubility. UV-vis spectroscopy indicated a bathochromic shift of the porphyrin Soret band upon binding to the nanotube surface, while Raman spectroscopy indicated that functionalization with the porphyrin dimer does not lead to any defects being formed on the nanotube wall. Transmission electron microscopy revealed the presence of individual nanotubes and small nanotube bundles that were heavily coated with porphyrin dimers. Comparison to analogous fused dimers bearing tert-butyl groups for solubility clearly demonstrated that long alkyl chains are necessary for prolonged solution stability of the nanotube complexes. While a previously investigated tert-butyl derivative was found to bind to the nanotube surface, the resulting complex precipitated out of solution within minutes. It was also found that the position of bulky substituents on the porphyrin dimer had a dramatic effect on whether it was able to interact with the nanotube surface. © 2011 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Steacie Institute for Molecular Sciences (SIMS-ISSM)
Peer reviewedYes
NPARC number21271083
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Record identifierb5639eec-5b5d-4c3a-9699-2b496dcc49f3
Record created2014-03-24
Record modified2016-05-09
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