Radical Addition of a Conjugated Polymer to Multilayer Fullerenes (Carbon Nano-onions)

Rettenbacher, Arno S.; Perpall, Mark W.; Echegoyen, Luís; Hudson, Joan; Smith, Dennis W.

doi:10.1021/cm0626132

Cited by 70 publications

(36 citation statements)

References 21 publications

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“…Tour et al [23] firstly ran a radical polymerization via a thermally-triggered Bergman cyclization and obtained conjugated aromatic polymers such as poly(p-phenylene)s (PPPs) and polynaphthalenes (PNs) in 1994, thereby highlighting the Bergman cyclization as a new synthetic tool for polymers or other materials. Smith and co-workers [24,25] subsequently used the Bergman cyclization of bis(o-diynylarene) to form branched oligomers at 210 °C, which could either react with carbon nano-onions to improve their solubility, or be carbonized to generate glassy carbon. Moore et al [26,27] used diradicals generated via a Bergman cyclization to initiate the radical polymerization of a variety of vinyl monomers.…”

Section: Introductionmentioning

confidence: 99%

Recent advances of the Bergman cyclization in polymer science

Chen

2015

Sci. China Chem.

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The Bergman cyclization has strongly impacted on a number of fields including pharmaceutics, synthetic chemistry, and material science. The diradical intermediates stemmed from enediynes can not only cause DNA cleavage under physiological conditions but also function as monomer or initiator participants in polymer science. The homo-polymerization of enediynes through the Bergman cyclization to fabricate conjugated polymers is a fascinating strategy due to the advantages of facial operation, high efficiency, tailored structure, and catalyst-free operation. Moreover, conjugated polymers generated through the Bergman cyclization show many remarkable properties, such as excellent thermal stability, good solubility, and processability, which enables these polymers to be further manufactured into carbon-rich materials. Recent times have seen extensive efforts devoted to the application of the Bergman cyclization in polymer science and materials chemistry. A variety of synthetic strategies have been developed to fabricate structurally unique materials via the Bergman cyclization, including the fabrication of rod-like polymers with polyester, dendrimers and chiral imide side chains, functionalization of carbon nanomaterials by surface-grafting conjugated polymers, formation of nanoparticles by intramolecular collapse of single polymer chains, and the construction of carbon nanomembranes with different morphologies. Future developments involving the Bergman cyclization in polymer science, probably by altering the reaction mechanism to precisely control the microstructure of polymeric products, are also proposed in this review article.

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Section: Introductionmentioning

confidence: 99%

Recent advances of the Bergman cyclization in polymer science

Chen

2015

Sci. China Chem.

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“…These properties make them suitable for applications such as the encapsulation of foreign materials [25,26], catalyst supports [27] and lubricant additives [28,29]. The combination of CNOs with polymers obtains novel materials with great potential in a wide range of different applications including optical limiting [12,30,31], energy and gas stores [32,33], anode materials for Lithium-Ion Batteries [34] and additives for capacitor devices [35].…”

Section: When Kroto and Mckaymentioning

confidence: 99%

Method to obtain carbon nano-onions by pyrolisys of propane

2013

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“…Initial trial was documented by Smith and coworkers [18] since Bergman cyclization of BODA (vide supra) have already been well investigated in their lab (Scheme 10). The suspension of pretreated carbon nano-onions (CNOs) and BODAs in NMP was ultrasonicated, then refluxed for 4 d. The gained BODA-CNO copolymers covered two fractions: partially BODA-functionalized CNOs that could only dissolved in the highly polar solvent NMP and highly BODAfunctionalized CNOs soluble in both NMP and CHCl 3 .…”

Section: Surface Modification Of Carbon Materialsmentioning

confidence: 99%

Bergman Cyclization in Polymer Chemistry and Material Science

Xiao

2011

Macromol. Rapid Commun.

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Bergman cyclization of enediynes, regarded as a promising strategy for anticancer drugs, now finds its own niche in the area of polymer chemistry and material science. The highly reactive aromatic diradicals generated from Bergman cyclization can undergo polymerization acting as either monomers or initiators of other vinyl monomers. The former, namely homopolymerization, leads to polyphenylenes and polynaphthalenes with excellent thermal stability, good solubility, and processability. The many remarkable properties of these aromatic polymers have further endowed them to be manufactured into carbon-rich materials, e.g., glassy carbons and carbon nanotubes. Whereas used as initiators, enediynes provide a novel resource for high molecular weight polymers with narrow polydispersities. The aromatic diradicals are also useful for introducing oligomers or polymers onto pristine carbonous nanomaterials, such as carbon nano-onions and carbon nanotubes, to improve their dispersibility in organic solvents and polymer solutions.

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Radical Addition of a Conjugated Polymer to Multilayer Fullerenes (Carbon Nano-onions)

Cited by 70 publications

References 21 publications

Recent advances of the Bergman cyclization in polymer science

Recent advances of the Bergman cyclization in polymer science

Method to obtain carbon nano-onions by pyrolisys of propane

Bergman Cyclization in Polymer Chemistry and Material Science

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