[60]Fullerene as a Substituent

Bagno, Alessandro; Claeson, Sofia; Maggini, Michele; Martini, Maria Luisa; Prato, Maurizio; Scorrano, Gianfranco

doi:10.1002/1521-3765(20020301)8:5<1015::aid-chem1015>3.0.co;2-q

Cited by 60 publications

(58 citation statements)

References 18 publications

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“…[2][3][4] Although pristine C 60 can form nanocrystalline preparations that have been reported to have biological activity, 5-8 most workers have studied chemically modified or functionalized fullerenes that acquire solubility in water or biologically compatible solvents and thereby have increased versatility. [9][10][11][12] Photodynamic therapy (PDT) is a rapidly advancing treatment for multiple diseases and is based on the administration of a nontoxic drug or dye known as a photosensitizer (PS) either systemically, locally, or topically to a patient bearing a lesion (frequently but not always cancer13), followed after some time by the illumination of the lesion with visible light, which activates the PS and, in the presence of oxygen, leads to the generation of cytotoxic reactive oxygen species and consequently to cell death and tissue destruction.14 -16 The light is absorbed by the PS molecule, and an electron is excited to the first excited singlet state. In addition to losing energy by fluorescence or internal conversion, the excited singlet can undergo the process known as intersystem crossing to the long-lived triplet state.…”

Section: Introductionmentioning

confidence: 99%

Photodynamic therapy with fullerenes

Mróz

Tegos

Gali

et al. 2007

Photochem Photobiol Sci

276

209

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Fullerenes are a class of closed-cage nanomaterials made exclusively from carbon atoms. A great deal of attention has been focused on developing medical uses of these unique molecules especially when they are derivatized with functional groups to make them soluble and therefore able to interact with biological systems. Due to their extended π-conjugation they absorb visible light, have a high triplet yield and can generate reactive oxygen species upon illumination, suggesting a possible role of fullerenes in photodynamic therapy. Depending on the functional groups introduced into the molecule, fullerenes can effectively photoinactivate either or both pathogenic microbial cells and malignant cancer cells. The mechanism appears to involve superoxide anion as well as singlet oxygen, and under the right conditions fullerenes may have advantages over clinically applied photosensitizers for mediating photodynamic therapy of certain diseases.

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Section: Introductionmentioning

confidence: 99%

Photodynamic therapy with fullerenes

Mróz

Tegos

Gali

et al. 2007

Photochem Photobiol Sci

276

209

View full text Add to dashboard Cite

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“…* In polar media, delocalization of the nitrogen lone pair of the pyrrolidine ring fused to fullerene leads, due to interaction of this lone pair with the π system of fullerene, to an increase in the acidity by several orders of magnitude and a decrease in the reactivity of the pyrrolidine nitrogen atom, for example, in N methyl 1 (n alkyl)fullerenopyrrolidine. 19,20 of the fullerene fragment, which is manifested in a larger shift of the first reduction peak of compound 1 to nega tive potentials compared to the 4 pyridyl derivative of fullerenopyrrolidine (C 60 4 py). 21 In addition, the elec tron withdrawing properties of the substituent C 60 are rather weak (σ = 0.06).…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic study of the reaction of cis-1,3-di(2-pyridyl)[60]fullereno[1,2-c]pyrrolidine and 2-(2-pyridylmethyl)-1,3-di(2-pyridyl)[60]fullereno[1,2-c]pyrrolidine with zinc meso-tetraphenylporphyrinate

et al. 2005

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Spectroscopic study of the reaction of cis 1,3 di(2 pyridyl)[60]fullereno[1,2 c]pyrrolidine and 2 (2 pyridylmethyl) 1,3 di(2 pyridyl)[60]fullereno[1,2 c]pyrrolidine with zinc meso tetraphenylporphyrinateAxial coordination of the pyrrolidine nitrogen atom in cis 1,3 di(2 pyridyl)[60]fulle reno[1,2 c]pyrrolidine to zinc meso tetraphenylporphyrinate in cyclohexane gives rise to a donor acceptor complex. The formation constant of the 1 : 1 porphyrin-fullerenopyrrolidine complex was determined by spectrophotometric and fluorescence titration. The values of the constant estimated by spectrophotometric and fluorescence methods are 1.2•10 4 and 9.7•10 3 L mol -1 , respectively.

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“…However, the lower basicity of NH-pyrrolidine [60]fullerenes compared with their analogs without fullerene, by six orders of magnitude [46], makes the alkylation of the amino moiety a particularly difficult process.…”

Section: Azomethine Ylidesmentioning

confidence: 99%

“…For example, the 3 -(N-phenylpyrazolyl)isoxazolino [60] fullerene dyad (46) was prepared in 22% yield from the corresponding nitrile oxide (Scheme 23.17) [60]. Longer reaction times afforded larger amounts of bisadducts.…”

Section: Nitrile Oxidesmentioning

confidence: 99%

Application of Microwave Irradiation in Carbon Nanostructures

Langa

Cruz

2012

Microwaves in Organic Synthesis

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Fullerenes Under Microwave Irradiation IntroductionSince Krätschmer and co-workers discovered a procedure for the preparation of bulk quantities of C 60 [1] in the early 1990s, the physical properties of fullerenes have been intensively investigated. However, members of this new family of compounds are insoluble or sparingly soluble in most solvents [2] and, consequently, C 60 is difficult to handle. Chemical functionalization allows the preparation of soluble C 60 derivatives that maintain the electronic properties of fullerenes. For this reason, the chemistry and derivatization of fullerenes has continued to attract attention aimed at preparing derivatives with interesting physical properties and biological activities [3]. New materials based on C 60 derivatives have shown promise in the fields of material science [4], solar energy conversion [5], nonlinear optical behavior [6], superconductivity [7], ferromagnetism [8], medicinal chemistry [9], and HIV-1 protease inhibition [10].Among the suitable procedures for the functionalization of fullerenes (Scheme 23.1) [11], cycloadditions provide a powerful tool as C 60 behaves as an electron-deficient olefin with a relatively low-lying LUMO (−3.14 eV) [12,13].As a consequence, a large variety of cycloaddition reactions have been carried out [12, 14] in which C 60 (1) is the reactive 2π component. In this context, [1 + 2]-, [2 + 2]-, [3 + 2]-, and [4 + 2]-cycloadditions have all been performed (Scheme 23.2) and the conditions for cycloadduct formation depend strongly on the gap between the controlling orbitals. For this reason, it is frequently necessary to use harsh conditions involving several hours (or days) under reflux in high-boiling solvents. As microwave irradiation has been successfully used in cycloaddition reactions solving problems concerning reversibility and decomposition of reagents and/or products, it was evident to use this methodology in fullerene chemistry as most fullerene derivatives are prepared by Diels-Alder [15] or 1,3-dipolar cycloaddition reactions [16].Microwaves in Organic Synthesis, Third Edition.

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[60]Fullerene as a Substituent

Cited by 60 publications

References 18 publications

Photodynamic therapy with fullerenes

Photodynamic therapy with fullerenes

Spectroscopic study of the reaction of cis-1,3-di(2-pyridyl)[60]fullereno[1,2-c]pyrrolidine and 2-(2-pyridylmethyl)-1,3-di(2-pyridyl)[60]fullereno[1,2-c]pyrrolidine with zinc meso-tetraphenylporphyrinate

Application of Microwave Irradiation in Carbon Nanostructures

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