Syntheses and properties of macromolecular fullerenes, a review

Geckeler, Kurt E.; Samal, Shashadhar

doi:10.1002/(sici)1097-0126(199909)48:9<743::aid-pi246>3.0.co;2-4

Cited by 114 publications

(14 citation statements)

References 76 publications

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“…The area of fullerene functionalization with synthetic macromolecules is relatively extensive and C 60 has been modified via various approaches. [2][3][4][5] Despite the diverse routes to functional fullerenes, only a few are highly efficient and specific. [6] The functionalization of fullerenes with polymeric chains does not only modify the properties of the polymers, but the chemical modification of fullerenes renders them into a processable form.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of Fullerenes with Cyclopentadienyl and Anthracenyl Capped Polymeric Building Blocks via Diels–Alder Chemistry

Nebhani¹,

Barner‐Kowollik²

2010

Macromol. Rapid Commun.

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Cyclopentadienyl (Cp) capped polymers [polyethylene glycols (PEGs), $\overline M _{\rm n}$ = 2 000 g · mol(-1) ], react readily with fullerenes in a 1:1 molar ratio (relative to the amount of fullerenes and Cp-end groups) at ambient temperature within 5 min in the absence of any catalyst in a Diels-Alder (DA) reaction to provide fullerene-PEG hybrids. Similarly, anthracenyl capped PEGs react with fullerenes (in a 1:3 molar ratio) in DA reactions to yield the corresponding hybrids, albeit over a period of 1.5 h at 80 °C and a lesser conversion. The efficiency of the transformation is monitored via electrospray ionization mass spectrometry (ESI-MS), demonstrating that the fullerenes can be transformed into polymer hybrids; most efficiently when Cp-functional polymer is used as the diene. In addition, the obtained hybrids were subjected to UV/Vis as well as thermogravimetric analysis further underpinning the formation of mono-substituted C(60) -PEG hybrids [wt.-%(exp) 70 ± 5 (PEG), 30 ± 5 (C(60) ), wt.-%(theo) 68 (PEG), 32 (C(60) )].

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Section: Introductionmentioning

confidence: 99%

Functionalization of Fullerenes with Cyclopentadienyl and Anthracenyl Capped Polymeric Building Blocks via Diels–Alder Chemistry

Nebhani¹,

Barner‐Kowollik²

2010

Macromol. Rapid Commun.

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“…An interesting approach consists of the functionalization of fullerenes by macromolecules so as to combine the physico-and photochemical properties of C 60 with the mechanical and solubility properties of polymers. [20][21][22] Nowadays a wide variety of polymeric fullerene derivatives is available mainly by addition of polymer chains that bear azide [23,24] or amine groups, [25,26] and anionic [27,28] and radical [29][30][31] species onto fullerene.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Poly(vinyl alcohol)/C₆₀ and Poly(N‐vinylpyrrolidone)/C₆₀ Nanohybrids as Potential Photodynamic Cancer Therapy Agents

Hurtgen

Debuigne

Mouithys-Mickalad

et al. 2010

Chemistry An Asian Journal

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Well-defined poly(vinyl acetate) (PVAc) and poly(N-vinylpyrrolidone)-co-poly(vinyl acetate) (PNVP-co-PVAc) chains end-capped by Co(acac)(2) (acac=acetylacetonate) and prepared by cobalt-mediated radical polymerization (CMRP) are grafted onto a fullerene. Homolytic Co-C bond cleavage of the polymer chain ends at 30 degrees C releases the polymeric radicals that add onto C(60), thereby leading to the corresponding PVAc/C(60) and PNVP-co-PVAc/C(60) nanohybrids. The [polymer-Co(acac)(2)]/[C(60)] molar ratio was varied to adjust the structure of the nanohybrids, and more particularly the number of grafted arms. Finally, the potential of the hydrosoluble PVOH/C(60) nanohybrids, which result from the methanolysis of the ester groups of PVAc/C(60), and of the PNVP-co-PVAc/C(60) nanohybrids as photosensitizers for photodynamic therapy (PDT), was approached. First, photobleaching tests demonstrated the ability of these nanohybrids to produce singlet oxygen upon irradiation, which can play a role in cell damage. Second, cell viability assays demonstrated that both types of nanohybrids are deprived of intrinsic cytotoxicity in the dark, whereas they promoted significant cell mortality when subjected to light treatment. The selective response of these materials to irradiation makes them promising compounds for PDT.

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“…21 C 60 molecules can be introduced into the main chain of an organic polymer to form a 'pearl necklace' polymer, in which the C 60 units are part of the polymer chain, or into the side chain of a polymer as a pendant group to form a 'charm bracelet' polymer. [22][23][24][25][26] The latter approach is especially interesting as C 60 moieties could be directly linked to a soluble preformed polymer by following different synthetic procedures. [27][28][29][30] The remarkable retention of the electronic structure of the C 60 moieties observed by UV-vis spectroscopy and cyclic voltammetry is a very encouraging result, 31 which augurs well for the observation of unusual fullerene-type properties in products obtained from these polymers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a [60] fullerene—Functionalized isotactic polypropylene derivative

Martínez

Gómez

Marco

et al. 2008

J. Polym. Sci. A Polym. Chem.

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The covalent attachment of [60] fullerene (C 60 ) to isotactic polypropylene (i-PP) is achieved by direct reaction in 1,2,4-trichlorobenzene (TCB) solution in the presence of dicumyl peroxide (DCP). The chemically modified pendant C 60 /i-PP polymers are soluble in chlorinated solvents and have been characterized by ultravioletvisible and fourier transform infrared spectroscopy, scanning electron microscopy, X-ray diffraction, differential scanning calorimetry, cyclic voltametry, and thermogravimetric analysis. From the results it can be concluded that the modification of i-PP by grafting via a free-radical reaction competes with the possibility of chain scission of i-PP due to the presence of DCP. The functionalized polymers crystallize in the monoclinic crystal modification, and have high crystallinity. The incorporation of C 60 significantly enhances the thermal stability of the i-PP. Electrochemical measurements demonstrate good electron acceptor properties of the fullerenated i-PP samples. V V C 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 6722-6733, 2008

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Syntheses and properties of macromolecular fullerenes, a review

Cited by 114 publications

References 76 publications

Functionalization of Fullerenes with Cyclopentadienyl and Anthracenyl Capped Polymeric Building Blocks via Diels–Alder Chemistry

Functionalization of Fullerenes with Cyclopentadienyl and Anthracenyl Capped Polymeric Building Blocks via Diels–Alder Chemistry

Synthesis of Poly(vinyl alcohol)/C₆₀ and Poly(N‐vinylpyrrolidone)/C₆₀ Nanohybrids as Potential Photodynamic Cancer Therapy Agents

Synthesis of a [60] fullerene—Functionalized isotactic polypropylene derivative

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Syntheses and properties of macromolecular fullerenes, a review

Cited by 114 publications

References 76 publications

Functionalization of Fullerenes with Cyclopentadienyl and Anthracenyl Capped Polymeric Building Blocks via Diels–Alder Chemistry

Functionalization of Fullerenes with Cyclopentadienyl and Anthracenyl Capped Polymeric Building Blocks via Diels–Alder Chemistry

Synthesis of Poly(vinyl alcohol)/C60 and Poly(N‐vinylpyrrolidone)/C60 Nanohybrids as Potential Photodynamic Cancer Therapy Agents

Synthesis of a [60] fullerene—Functionalized isotactic polypropylene derivative

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Synthesis of Poly(vinyl alcohol)/C₆₀ and Poly(N‐vinylpyrrolidone)/C₆₀ Nanohybrids as Potential Photodynamic Cancer Therapy Agents