Microwave-assisted sidewall functionalization of single-wall carbon nanotubes by Diels–Alder cycloaddition

Delgado, Juan Luis; Cruz, Pilar de la; Langa, Fernando; Urbina, Antonio; Casado, Juan; Navarrete, Juan T. López

doi:10.1039/b402375g

Cited by 157 publications

(107 citation statements)

References 27 publications

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“…Diels-Alder reactions under microwave conditions have also been used to modify singlewall carbon nanotubes (SWNT). [301] Two recent review articles highlight the importance of microwave chemistry for carbohydrate chemistry. [302] The authors work in the area of microwave chemistry has been generously supported by the Austrian Science Fund (FWF, P15582, and I18-N07), the "Jubiläumsfonds der Österreichi-schen Nationalbank" (ÖNB, Project 7904), and various industrial contributors.…”

Section: Addendummentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: Addendummentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…The possibility of the DA reaction has been studied theoretically since 2002. [25] It has been proved experimentally that the DA reaction can be performed on CNT either assisted by microwaves [26] or by using fluorinated CNT [27] or by metal complex catalyzed high pressure reactions. [28] However, these methods are performed using reactants without further functional groups.…”

Section: Introduction Amentioning

confidence: 99%

Functionalization of Carbon Materials using the Diels‐Alder Reaction

Munirasu

Albuerne

Boschetti‐de‐Fierro

et al. 2010

Macromol. Rapid Commun.

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A simple and efficient Diels-Alder (DA) reaction on carbon material has been demonstrated.The present work involves single and multiwall carbon nanotubes (CNT), as well as Herringbone carbon nanofiber. The CNTs show a dual nature of reactivity in DA reaction, i.e. they behave both as dienophile and diene with furfuryl groups and maleic anhydride derivatives, respectively. Various functional groups, including alcohol, amine, epoxy, carboxylic and ester have been introduced on the carbon materials. The results suggest that the reactivity of CNT in DA reaction may resemble the chemistry of small molecules.

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“…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.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Studies of Substitutionally Doped Single-Walled Nanotubes

Yeung

Chen

Wang

2010

Journal of Nanotechnology

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The rich chemistry of single-walled carbon nanotubes (SWCNTs) is enhanced by substitutional doping, a process in which a single atom of the nanotube sidewall is replaced by a heteroatom. These so-called heteroatom-substituted SWCNTs (HSWCNTs) exhibit unique chemical and physical properties not observed in their corresponding undoped congeners. Herein, we present theoretical studies of both main group element and transition metal-doped HSWCNTs. Within density functional theory (DFT), we discuss mechanistic details of their proposed synthesis from vacancy-defected SWCNTs and describe their geometric and electronic properties. Additionally, we propose applications for these nanomaterials in nanosensing, nanoelectronics, and nanocatalysis.

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Microwave-assisted sidewall functionalization of single-wall carbon nanotubes by Diels–Alder cycloaddition

Abstract: The first Diels-Alder cycloaddition of o-quinodimethane to SWNT has been performed under microwave irradiation.

Cited by 157 publications

References 27 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Functionalization of Carbon Materials using the Diels‐Alder Reaction

Theoretical Studies of Substitutionally Doped Single-Walled Nanotubes

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