Synthesis of multiporphyrinic α-polypeptides: towards the study of the migration of an excited state for the mimicking of the natural light harvesting device

Solladié, Nathalie; Hamel, Arnaud; Gross, Maurice

doi:10.1016/s0040-4039(00)01049-2

Cited by 57 publications

(76 citation statements)

References 19 publications

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“…The details of synthesis of porphyrin-peptide oligomers have been reported previously. 16 Nanostructured SnO 2 films were cast on an optically transparent electrode (OTE) by applying a 2% colloidal solution obtained from Alfa Chemicals. The air-dried films were annealed at 673 K. The details of the preparation of SnO 2 films on conducting glass substrates were reported elsewhere.…”

Section: Experimental Materialsmentioning

confidence: 99%

“…15 In this context, we have recently reported synthesis of porphyrin oligomers with polypeptidic backbones in which porphyrins are held in a favored spacing and orientation by fairly short helical polypeptides. 16 With regard to electron acceptors, fullerene, which is an extensively conjugated three-dimensional p system, is an ideal electron acceptor because of the minimal changes of structure and solvation associated with the electron-transfer reduction. 17 Thus, the combination of porphyrin and fullerene is regarded as an ideal donor-acceptor couple, since the combination results in a small reorganization energy, which accelerates photoinduced electron transfer and slows charge recombination, leading to the generation of a long-lived charge-separated state with a high quantum yield.…”

Section: Introductionmentioning

confidence: 99%

“…28 We have investigated the effects of the number of porphyrins in a polypeptide unit [P(H 2 P) n (n = 1, 2,4,8,16) and P(ZnP) n (n = 1, 2, 4, 8, 16)] and of the types of porphyrins (H 2 P vs. ZnP) and fullerenes (C 60 vs. C 60 derivatives) in Fig. 1 on the structures, spectroscopic, and photoelectrochemical properties of the porphyrin-C 60 composite electrodes.…”

Section: Introductionmentioning

confidence: 99%

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Organic solar cells. Supramolecular composites of porphyrins and fullerenes organized by polypeptide structures as light harvesters

et al. 2007

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We have constructed supramolecular solar cells composed of a series of porphyrin-peptide oligomers [porphyrin functionalized a-polypeptides, P(H 2 P) n or P(ZnP) n (n = 1, 2, 4, 8, 16)], and fullerenes assembled on a nanostructured SnO 2 electrode using an electrophoretic deposition method. Remarkable enhancement in the photoelectrochemical performance as well as the broader photoresponse in the visible and near-infrared regions is seen with increasing the number of porphyrin units in a-polypeptide structures. Formation of supramolecular clusters of porphyrins and fullerenes prepared in acetonitrile-toluene = 3 : 1 has been confirmed by transmission electron micrographs (TEM) and the absorption spectra. The highly colored composite clusters of porphyrin-peptide oligomers and fullerenes have been assembled as threedimensional arrays onto nanostructured SnO 2 films using an electrophoretic deposition method. A high power conversion efficiency (g) of y1.6% and the maximum incident photon-tophotocurrent efficiency (IPCE = 56%) were attained using composite clusters of free base and zinc porphyrin-peptide hexadecamers [P(H 2 P) 16 and P(ZnP) 16 ] with fullerenes, respectively. Femtosecond transient absorption and fluorescence measurements of porphyrin-fullerene composite films confirm improved electron-transfer properties with increasing number of porphyrins in a polypeptide unit. The formation of molecular assemblies between porphyrins and fullerenes with a polypeptide structure controls the electron-transfer efficiency in the supramolecular complexes, meeting the criteria required for efficient light energy conversion.

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Section: Experimental Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Organic solar cells. Supramolecular composites of porphyrins and fullerenes organized by polypeptide structures as light harvesters

et al. 2007

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“…2). 9 An iterative synthetic strategy was developed for the preparation of the oligomers, based on the choice of mild conditions for the selective deprotection of both allyl and BOC groups. The BOC protective group of 2 was cleaved with 91% yield by stirring the substrate for 2 h at room temperature in a 1 M solution in dichloromethane of trimethylsilylchloride and phenol.…”

Section: Resultsmentioning

confidence: 99%

Towards multiporphyrinic α‐helices with a polypeptidic backbone as system endowed with light harvesting capabilities

Solladié¹,

Hamel²,

Gross³

2001

Chirality

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“…The unavailability of a vaccine and the spread and intensification of drug resistance over the past [15][16][17][18][19][20] years have led to a dramatic decline in the efficacy of the most affordable antimalarial drugs. [1][2][3] In order to circumvent that situation, medications based on the association of two substances acting against the parasite have been developed.…”

Section: Introductionmentioning

confidence: 99%

High Antiplasmodial Activity of Novel Plasmepsins I and II Inhibitors

et al. 2006

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The aim of this study was to develop new antiplasmodial compounds acting through distinct mechanisms during both the liver and the blood stages of the parasite life cycle. Compounds were designed on the basis of the “double-drug” approach: primaquine, which has been linked to statine-based inhibitors of plasmepsins (PLMs), the plasmodial aspartic proteases involved in degradation of hemeoglobin. The compounds were tested in vitro for anti-PLM I/PLM II activities and against chloroquine-sensitive (D10) and chloroquine-resistant (W2) strains of P. falciparum. An antiplasmodial activity (IC50) as low as 0.1 μM was obtained, an excellent improvement in comparison with inhibitors previously reported (IC50 = 2−20 μM). The killing activity was equally directed against both P. falciparum strains and was correlated to lipophilicity (calculated as ALogP), for all compounds but one (9). All compounds inhibited PLM I and PLM II in the nanomolar range (K i = 1−700 nM). The most promising compounds (2, 6, 10) were not cytotoxic against human fibroblasts at 100 μM and were highly selective for PLMs vs human cathepsin D.

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Synthesis of multiporphyrinic α-polypeptides: towards the study of the migration of an excited state for the mimicking of the natural light harvesting device

Cited by 57 publications

References 19 publications

Organic solar cells. Supramolecular composites of porphyrins and fullerenes organized by polypeptide structures as light harvesters

Organic solar cells. Supramolecular composites of porphyrins and fullerenes organized by polypeptide structures as light harvesters

Towards multiporphyrinic α‐helices with a polypeptidic backbone as system endowed with light harvesting capabilities

High Antiplasmodial Activity of Novel Plasmepsins I and II Inhibitors

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