Fullerene-containing porphyrins: Synthesis and potential practical applications

Karmova, Fatima M.; Lebedeva, V. S.; Mironov, A. F.

doi:10.1134/s1070363216090322

Cited by 9 publications

(2 citation statements)

References 81 publications

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“…Currently, active work is underway to create photoactive structures based on fullerene-dye dyads for photovoltaics and a number of other applications. [1,2] These dyads are of particular interest for photodynamic therapy as photosensitizers, since fullerene C 60 has extremely high photoactivity -under light excitation it is capable of passing to an excited triplet state with almost 100 % quantum yield [3,4] and effectively generate reactive oxygen species (ROS).…”

Section: Introductionmentioning

confidence: 99%

Pyropheophorbide-Fullerene Dyad: Synthesis and Photochemical Properties

Rybkin¹,

Belik²,

Tarakanov³

et al. 2019

MHC

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The methylpyropheophorbide-fullerene[60] dyad was synthesized by 1,3-dipolar cycloadditions of the corresponding azomethine ylide to C 60 (Prato reaction). Using the mass spectrometric method with soft matrix-activated ionization it was possible to achieve a significant reduction in fragmentation processes by the retro-Diels-Alder reaction, which allows to reliably detect the presence of polyadducts of azomethine ylide cycloadditions to fullerene. The use of gel permeation chromatography under conditions of weakening of the intermolecular π-π interaction between methylpyropheophorbide and fullerene moieties makes it possible to effectively separate mixed products with ~ 1.5 fold difference in molecular weight. It has been shown that the fluorescence of the dyad is quenched more than 5000 times (compared to the native dye). The singlet oxygen quantum yield of the dyad is 360 times less than that for the native methylpyropheophorbide a, however, its efficiency of superoxide generation increases by 18.5 times. The obtained result agrees well with the previously reported mechanism of relaxation of the excited state of the dyad through a charge-separated state, which can lead to the formation of superoxide. The observed effects indicate a change in the mechanism of photodynamic activity from type II (generation of singlet oxygen) for the native dye to type I (generation of superoxide) for the dyad, which shows a promising method of creation of highly efficient photosensitizers based on similar dye-fullerene[60] dyads.

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Section: Introductionmentioning

confidence: 99%

Pyropheophorbide-Fullerene Dyad: Synthesis and Photochemical Properties

Rybkin¹,

Belik²,

Tarakanov³

et al. 2019

MHC

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“…[5] There have been published a considerable number of papers on molecular photosystems based on porphyrins and fullerenes synthesis (beginning with simple donor-acceptor dyads till multichromophoric systems), as well as on supramolecular structures using different kinds of non-covalent interactions (hydrogen bonds, anion Advances in the Synthesis of Porphyrin-Fullerenes binding, metal-ligand coordination, crown ether-ammonium cation binding, electrostatic interactions and π-πstacking) in order to simulate natural photosynthetic systems and to study the basic principles of the photoinduced energy and electron transfer in antenna-reaction centers, as well as with the aim of creation of artificial storage and energy transfer systems. [6][7][8][9][10][11][12][13][14][15][16][17][18] For a number of the covalent-bound porphyrin-fullerene systems the charge-separation lifetime was comparable and even exceeded the lifetime of the charge-separated state in the natural bacterial photosynthetic reactive center.…”

Section: Introductionmentioning

confidence: 99%