Reactions of fluoroalkanoyl peroxides with single‐walled carbon nanotubes: application to sidewall modification of single‐walled carbon nanotubes with the introduction of fluoroalkyl groups

Abstract

Fluoroalkanoyl peroxides reacted with single‐walled carbon nanotubes (SW‐CNTs) to afford fluoroalkylated SW‐CNT derivatives under very mild conditions. Fluoroalkylated SW‐CNT derivatives [RF‐(SW‐CNT)s] thus obtained exhibited no solubility in aqueous and traditional organic media; however, RF‐(SW‐CNT)s were solubilized into water more effectively than the parent SW‐CNT by the use of fluoroalkyl end‐capped homooligomers. However, fluroalkyl end‐capped SW‐CNT cooligomers were obtained by the reactions of fluroalkanoyl peroxides with SW‐CNTs in the presence of radical polymerizable monomers, and these fluoralkylated SW‐CNT cooligomers were found to exhibit a good solubility in aqueous and organic media. Copyright © 2006 John Wiley & Sons, Ltd.

Adsorption of Small Gas Molecules onto Pt-Doped Single-Walled Carbon Nanotubes

“…26 However, it has been shown that the electronic properties of these materials can be altered through doping 27 or functionalization. 3,[28][29][30][31][32][33][34][35][36] Recently, our group has proposed a transformation whereby one of the carbon atoms in the sidewall is replaced with a transition metal. 37,38 This newly incorporated metal atom serves as a locus for reactivity and displays characteristics of classical organometallic complexes.…”

Theoretical Studies of Substitutionally Doped Single-Walled Nanotubes

“…The nanotube length and diameter are l and d, respectively, while σ and θ are the molecular cross-section area and coverage, respectively [71]. From Table 9, the trend between the adsorbate species and net charge transfer is clear.…”

“…Additionally, analysis of the HOMO−LUMO gap may provide some insight. Peng and coworkers have previously suggested that charge transfer between the nanotube and adsorbate can result in a change in the conductance along the axis as described by the following relationship [71]:…”

“…Chemical functionalization of carbon nanotubes can easily disrupt the extended conjugation and reduce the electrical conductivity along the axis of the tube. In particular, covalent modification of the sidewalls of carbon nanotubes has been achieved [3] via strategies including tandem fluorination/nucleophilic substitution [54][55][56], ozonolysis [57,58], Diels-Alder cycloaddition [59,60], osmylation [61], hydroboration [62], dissolving metal reduction (Billups reaction) [63], carbene addition [64], nitrene addition [65], dipolar cycloaddition of azomethine ylides [66], vinyl carbonylation via zwitterionic intermediates [67,68], other electrophilic oxidations [69], radical alkylation [64,70], perfluoroalkylation [71,72], and arylation [73]. Current technologies suffer from low reactivity and/or poor selectivity.…”

Synthesis of Novel Cross-Linked Fluorinated Cooligomeric Nanoparticles: Synthetic Approach to Colloidal Stable Fluorinated Magnetic Nanocomposites

“…Partially fluorinated polymers, especially fluoroalkyl end-capped oligomers are attractive fluorinated functional materials, because they exhibit various unique characteristic such as high solubility, surface active properties, biological activities, and nanometer size-controlled selfassembled molecular aggregates which cannot be achieved by the corresponding non-fluorinated, randomly or blocktype fluoroalkylated polymers, and low-molecular weight fluorinated surfactants [1][2][3][4][5][6][7][8][9][10][11] . The self-assembled fluorinated molecular aggregates formed by fluoroalkyl end-capped oligomers could interact with fullerene and carbon nanotube as guest molecules in aqueous media to afford fluorinated molecular aggregates-fullerene and carbon nanotube nanocomposites, respectively in aqueous solutions [12][13][14][15] . However, the shape of these fluorinated molecular aggregates is in general easily exchangeable under a variety of conditions, and the encapsulated guest molecules should have an easy releasing characteristic from the aggregates cores to their outsides under these conditions 16) .…”