Preferred functionalization of metallic and small-diameter single walled carbon nanotubes via reductive alkylation

Wunderlich, D.; Hauke, Frank; Hirsch, Andreas

doi:10.1039/b716732f

Cited by 72 publications

(85 citation statements)

References 38 publications

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“…The subsequent reoxidation of the charged (pentyne) n -SWCNT n-intermediates by air yields neutral (pentyne) n -SWCNT derivatives, which exhibit pronounced dispersibility in organic solvents such as THF or o-DCB. In contrast to the corresponding reactions with alkylides [21,36,37] or amides, [38] lithium acetylide based reaction sequences require elevated temperatures. Therefore, in this study a variety of different solvents, for example, o-DCB, o-xylene or diglyme, were investigated to open a larger temperature window due to the higher boiling points of these solvents.…”

Section: Resultsmentioning

confidence: 97%

A Novel Diameter‐Selective Functionalization of SWCNTs with Lithium Alkynylides

et al. 2010

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Covalent functionalization by addition to the sidewalls ofsingle‐walled carbon nanotubes (SWCNTs) is one of the most important methods for the derivatization of carbon nanotubes. The nucleophilic addition of organometallic reagents (carbon‐ and nitrogen‐based carbanions) has recently become a widely used tool for the introduction of functional moieties onto the surface of this new carbon allotrope. The extension of this concept by the successful nucleophilic addition of in situ generated lithium acetylides to the SWCNT scaffold is presented herein. The chemically derivatized SWCNTs have been characterized in detail by TGA/MS, Raman, UV/Vis/NIR and fluorescence spectroscopy. On the basis of a detailed examination of the signals in the radial breathing‐mode region of the Raman spectra, the preferred functionalization of smaller‐diameter tubes has been clearly demonstrated.

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Section: Resultsmentioning

confidence: 97%

A Novel Diameter‐Selective Functionalization of SWCNTs with Lithium Alkynylides

et al. 2010

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“…The heterogeneous dispersion formed in the end is purged with water until pH remains neutral, filtered, washed and dried to receive functionalized nanotubes in terms of bucky pa- per. For the detailed procedure of synthesis of the different R n -SWCNTs see [10]. The resonant Raman measurements were carried out using a micro-Raman setup in backscattering geometry, the samples being excited by a dye laser with about 0.3 mW laser power on the samples.…”

Section: Sample Preparation and Experimental Setupmentioning

confidence: 99%

“…Experimentally, Wunderlich et al have recently shown these criteria for successful addition of organometallic compounds and also for the reductive alkylation to carbon nanotubes, showing the inversely proportional behaviour to the tube diameter. Additionally they report steric demands of the addends for the reactivity [10]. In this paper we show the diameter dependence of addition reactions, the added molecules both being electron rich moieties.…”

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confidence: 96%

Diameter dependence of addition reactions to carbon nanotubes

Müller

Maultzsch

Wunderlich³

et al. 2008

Physica Status Solidi (b)

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We present resonant Raman measurements on carbon nanotubes functionalized with primary alkyl groups of different chain length. From the resonance profiles of the radial breathing mode (RBM) we assign the chiral indices of the tubes in order to study the selective reactivity of different tubes. We focus on diameter dependence showing inversely proportional behaviour to diameter for both metallic and semiconducting nanotubes. (© 2008 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim)

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“…In particular, charging provides a means to process single-walled carbon nanotubes (SWCNTs), whilst avoiding aggressive sonication and time consuming centrifugation processes. Anionic nanotube (nanotubide) polyelectrolytes have been generated using reductive chemical (alkali metal naphthalide/THF 3 , alkali metal/ liquid ammonia 4,5 ) and electrochemical approaches 6 . The covalent chemistry of reduced carbon nanomaterials has also been studied extensively, extending to a whole library of electrophilic addition and radical-based surface modifications [7][8][9] that can be tailored to specific applications.…”

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confidence: 99%

Giant cationic polyelectrolytes generated via electrochemical oxidation of single-walled carbon nanotubes

et al. 2013

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Previously, reduced single-walled carbon nanotube anions have been used for effective processing and functionalization. Here we report individually separate and distinct (that is, discrete) single-walled carbon nanotube cations, directly generated from a pure anode using a non-aqueous electrochemical technique. Cyclic voltammetry provides evidence for the reversibility of this nanoion electrochemisty, and can be related to the complex electronic density of states of the single-walled carbon nanotubes. Fixed potentiostatic oxidation allows spontaneous dissolution of nanotube cations ('nanotubium'); Raman spectroscopy and transmission electron microscopy show that sequential fractions are purified, separating amorphous carbon and short, defective single-walled carbon nanotubes, initially. The preparation of nanotubium, in principle, enables a new family of nucleophilic grafting reactions for single-walled carbon nanotubes, exploited here, to assemble nanotubes on amine-modified Si surfaces. Other nanoparticle polyelectrolyte cations may be anticipated.

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Preferred functionalization of metallic and small-diameter single walled carbon nanotubes via reductive alkylation

Cited by 72 publications

References 38 publications

A Novel Diameter‐Selective Functionalization of SWCNTs with Lithium Alkynylides

A Novel Diameter‐Selective Functionalization of SWCNTs with Lithium Alkynylides

Diameter dependence of addition reactions to carbon nanotubes

Giant cationic polyelectrolytes generated via electrochemical oxidation of single-walled carbon nanotubes

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