SET Mechanism in the Functionalization of Single-Walled Carbon Nanotubes

Chattopadhyay, J.; Chakraborty, Soma; Mukherjee, Arnab; Wang, Runtang; Engel, Paul S.; Billups, W. E.

doi:10.1021/jp071746n

Cited by 54 publications

(68 citation statements)

References 38 publications

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“…11), nanotubes are typically treated with lithium metal in liquid ammonia followed by the addition of either alkyl iodides [153] , aryl iodides, [154] or aryl/alkyl sulfides. [155] The same group [156] has also broadened this reaction to the use of either lithium, sodium, or potassium in liquid ammonia to yield dodecylated tubes that are soluble in organic solvents. The fast electron transfer process from lithium to the nanotubes was associated with SWNT debundling, as observed by TEM and AFM.…”

Section: Alkylationmentioning

confidence: 98%

Functional Covalent Chemistry of Carbon Nanotube Surfaces

2009

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In this Progress Report, we update covalent chemical strategies commonly used for the focused functionalization of single‐walled carbon nanotube (SWNT) surfaces. In recent years, SWNTs have been treated as legitimate nanoscale chemical reagents. Hence, herein we seek to understand, from a structural and mechanistic perspective, the breadth and types of controlled covalent reactions SWNTs can undergo in solution phase, not only at ends and defect sites but also along sidewalls. We explore advances in the formation of nanotube derivatives that essentially maintain and even enhance their performance metrics after precise chemical modification. We especially highlight molecular insights (and corresponding correlation with properties) into the binding of functional moieties onto carbon nanotube surfaces. Controllable chemical functionalization suggests that the unique optical, electronic, and mechanical properties of SWNTs can be much more readily tuned than ever before, with key implications for the generation of truly functional nanoscale working devices.

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Section: Alkylationmentioning

confidence: 98%

Functional Covalent Chemistry of Carbon Nanotube Surfaces

2009

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“…The functionalization reactions of all the reductive CCNs are currently attributed to a SET mechanism 343,359,361 ( Figure 28) analogous to the reductive functionalization of reduced molecular polyaromatics; 362 in the key step, a reagent, typically an organohalide, accepts an electron from the doped conduction band of the carbon nanomaterial. The so-formed radical anion decomposes to form a neutral radical and an anionic leaving group.…”

Section: Mechanism Of Reductive Functionalizationmentioning

confidence: 99%

Charged Carbon Nanomaterials: Redox Chemistries of Fullerenes, Carbon Nanotubes, and Graphenes

et al. 2018

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Since the discovery of buckminsterfullerene over 30 years ago, sp 2 -hybridised carbon nanomaterials (including fullerenes, carbon nanotubes, and graphene) have stimulated new science and technology across a huge range of fields. Despite the impressive intrinsic properties, challenges in processing and chemical modification continue to hinder applications. Charged carbon nanomaterials (CCNs), formed via the reduction or oxidation of these carbon nanomaterials, facilitate dissolution, purification, separation, chemical modification, and assembly. This approach provides a compelling alternative to traditional damaging and restrictive liquid phase exfoliation routes. The broad chemistry of CCNs not only provides a versatile and potent means to modify the properties of the parent nanomaterial but also raises interesting scientific issues. This review focuses on the fundamental structural forms: buckminsterfullerene, single-walled carbon nanotubes, and single-layer graphene, describing the generation of their respective charged nanocarbon species, their interactions with solvents, chemical reactivity, specific (opto)electronic properties, and emerging applications. CONTENTS

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“…18,19 Using alkali metals dissolved in liquid ammonia is another method of generating solvated electrons that transfer to the CNTs to produce radical CNT anions. 20,21 This route has been employed for functionalization with a series of alkyl and aryl groups. Several extended works have demonstrated the efficiency and scalability of reduction functionalization on CNTs, 22À27 yet the similar approaches have yet to be investigated for the functionalization of BNNTs, neither by theory nor experiment.…”

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confidence: 99%

Covalent Functionalization of Boron Nitride Nanotubes via Reduction Chemistry

et al. 2015

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Access and use of this website and the material on it are subject to the Terms and Conditions set forth at Covalent functionalization of boron nitride nanotubes via reduction chemistry Shin, Homin; Guan, Jingwen; Zgierski, Marek Z.; Kim, Keun S.; Kingston, Christopher T.; Simard, Benoit http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/jsp/nparc_cp.jsp?lang=fr L'accès à ce site Web et l'utilisation de son contenu sont assujettis aux conditions présentées dans le site LISEZ CES CONDITIONS ATTENTIVEMENT AVANT D'UTILISER CE SITE WEB. NRC Publications Record / Notice d'Archives des publications de CNRC:http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/ctrl?action=rtdoc&an=21277400&lang=en http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/ctrl?action=rtdoc&an=21277400&lang=fr READ THESE TERMS AND CONDITIONS CAREFULLY BEFORE USING THIS WEBSITE.http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/jsp/nparc_cp.jsp?lang=en Vous avez des questions? Nous pouvons vous aider. Pour communiquer directement avec un auteur, consultez la première page de la revue dans laquelle son article a été publié afin de trouver ses coordonnées. Si vous n'arrivez pas à les repérer, communiquez avec nous à PublicationsArchive-ArchivesPublications@nrc-cnrc.gc.ca. Questions?Contact the NRC Publications Archive team at PublicationsArchive-ArchivesPublications@nrc-cnrc.gc.ca. If you wish to email the authors directly, please see the first page of the publication for their contact information. NRC Publications Archive Archives des publications du CNRCThis publication could be one of several versions: author's original, accepted manuscript or the publisher's version. / La version de cette publication peut être l'une des suivantes : la version prépublication de l'auteur, la version acceptée du manuscrit ou la version de l'éditeur. For the publisher's version, please access the DOI link below./ Pour consulter la version de l'éditeur, utilisez le lien DOI ci-dessous.http://doi.org/10.1021/acsnano.5b06523 ACS Nano, 9, 12, pp. 12573-12582, 2015-11-18 B oron nitride nanotubes (BNNTs) consist of seamless cylinders of alternating boron and nitrogen atoms in a hexagonal BN bonding network. 1,2 Since their first synthesis in 1995, 1 BNNTs have been considered as revolutionary materials due to their unique properties, which are as compelling as those of carbon nanotubes (CNTs). Despite their structural similarity to CNTs, BNNTs also exhibit a range of physical and chemical properties distinct from CNTs, which are mainly attributed to the partial ionic bonding character of BN. For example, the mixed ionic and covalent bonding nature of BNNTs results in their wide band gaps, around 6.0 eV independent of diameter and chirality. Figure 1 illustrates the calculated valence electron density distribution of a (6,6) CNT and BNNT. The valence charges of a CNT are equally distributed around C atoms, indicating a strong covalent CÀC bond network as well as the delocalized electrons, while the bonding electrons of BNNT are more concentrated around N atoms with an asymmetric charge distribu...

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SET Mechanism in the Functionalization of Single-Walled Carbon Nanotubes

Cited by 54 publications

References 38 publications

Functional Covalent Chemistry of Carbon Nanotube Surfaces

Functional Covalent Chemistry of Carbon Nanotube Surfaces

Charged Carbon Nanomaterials: Redox Chemistries of Fullerenes, Carbon Nanotubes, and Graphenes

Covalent Functionalization of Boron Nitride Nanotubes via Reduction Chemistry

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