Solubilization of single‐wall carbon nanotubes in aqueous solutions of calixarenes

Abstract

The present work reports the studies of the solubilization of single-wall carbon nanotubes in aqueous solutions of calix[4]resorcinarene derivatives and p-sulfonato-calix[n]arenes (n = 4, 6) modified by alkyl (butyl and dodecyl) substituents. The highest dispersion ability is demonstrated by calix[4]resocinarene, which bears aminomethyl groups on the upper rim and phosphorus-bearing alkyl fragments on the lower rim of calixarene. Optical absorption spectroscopy justifies the formation of stable suspensions of SWNT in aqueous solutions of calixarenes.

Selective diameter uptake of single-walled carbon nanotubes in water using phosphonated calixarenes and ‘extended arm’ sulfonated calixarenes

“…There have been limited studies on the specific use of watersoluble calixarenes for the solubilization of SWCNTs. Lobach et al investigated various types of amphiphilic macrocycles, such as different upper and lower rim functionalized calix [4]resorcinarene and p-sulfonato-calix[n]arenes (n ¼ 4, 6), modified by lower rim alkyl substituents (butyl and dodecyl), 32 with the ability to form stable suspensions of SWCNTs in aqueous media. Furthermore, Ogoshi et al focused on p-sulfonato-calix[n]arenes (n ¼ 4, 6, 8), with successful solubilization of SWCNTs with the higher order oligomers, with p-sulfonato-calix [8]arene forming a dimer as part of a supramolecular SWCNT network polymer.…”

“…We also report a detailed investigation into the effects of using 'extended arm' p-sulfonated calix [8] p-sulfonated calixarenes. 32,33 The 'extended arm' calixarenes have a higher hydrophobic surface area relative to the parent p-sulfonated calixarene.…”

Phosphorus-containing macrocyclic compounds: synthesis and properties

“…200 This characteristic feature of aminoalkylated derivatives of phosphorus-containing calix [4]resorcinols was employed in investigations aimed at improving the dispersion of carbon nanotubes in water to find new technological aspects of their application. 201 In addition, it was shown 197 ± 200 that self-associated supramolecular systems based on phosphorylated calix [4]resorcinols 232 and their aminomethylated derivatives 233 exhibit high catalytic activity in the hydrolysis of phosphonic acid esters and phosphorylation of polyethyleneimines.…”

Phosphorylated Aminoacetal in the Synthesis of New Acyclic, Cyclic, and Heterocyclic Polyphenol Structures

“…We have shown earlier that condensation of functionally substituted acetals with resorcinol and its derivatives in acidic media is a convenient method to prepare unique linear and cyclic polyphenols, namely, P,N‐containing calix[4]resorcinols , derivatives of diarylmethane series including those on macrocyclic framework , and imidazolidine‐2‐ones containing polyphenol fragments . It was determined that synthesized calix[4]resorcinols can be utilized in micellar catalysis and are able to complexation with rare earth metal ions and extraction of carbon nanotubes . Derivatives of diarylmethane series are of interest as polydentate ligands .…”