A novel synthesis of triple-deckered triporphyrin

Abdalmuhdi, I.; Chang, C. K.

doi:10.1021/jo00203a034

Cited by 56 publications

(21 citation statements)

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“…Synthetic bisporphyrins bridged by various spacers have been shown to be useful and promising for studies of the details of primary photosynthetic processes [5][6][7][8]. Currently much effort has been directed towards the creation and investigation of higher oligomers of porphyrins contain!ng three or more covalently linked macrocycles [9][10][11][12][13][14][15]. On the other hand, self-assembly of molecular units in the frame of non-covalent supramolecular chemistry [16] is a highly promising way in terms of tile considerable acceleration of constructing various architectures of light-harvesting and charge-transport systems.…”

Section: Introductionmentioning

confidence: 99%

Formation and optical properties of self-organized pentameric porphyrin arrays

Chernook

Rempel

Borczyskowski

et al. 1996

Chemical Physics Letters

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Principles of formation, electronic absorption and fluorescence spectra are reported for self-organized pentameric arrays of tetrapyrrolic macrocycles. In these arrays two molecules of Zn-porphyrin dimers, Zn(II)l,4-bis [5-(10,15,20+tri-p-hexylphenylporphyrinyl)]-benzene ((ZnHTPP) 2) are bound via one molecule of a tetrapyridyl-substituted free base of porphyrin or tetrahydroporphyrin. The process of self-assembly is based on the twofold coordination of the central Zn ions !n the dimer with the nitrogen atoms of the pyridyl rings in the free base which is strong enough to make the complexes stable at room temperature. The formation of the complexes can be followed by changes in the absorption bands of (ZnHTPP) 2 characteristic of an axial extra-ligation of Zn-porphyrins with pyridine or pyridyl-substituted compounds. The spectral behavior of the free bases in the pentads is determined by a non-planar distortion of their macrocycle caused by the two-point binding with the dimers. The fluorescence intensity of the Zn-porphyrin dimer decreases essentially upon complexation with the tetrapyridyl-substituted free bases. This quenching effect is assigned to a singlet-silaglet energy transfer from the complexed Zn-porphyrin dimers to the free base subunit in the pentad.

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Section: Introductionmentioning

confidence: 99%

Formation and optical properties of self-organized pentameric porphyrin arrays

Chernook

Rempel

Borczyskowski

et al. 1996

Chemical Physics Letters

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“…We were among the first to exploit this condensation and utilized this approach to prepared the heme models shown in Figure 9,74 starting with o ‐nitrobenzaldehyde to obtain atropisomers. If the aldehyde is already part of a porphyrin, such a condensation in one step gives the triple‐decker porphyrin 75. An extension of this approach furnished the impressive quintuple‐decker porphyrin 76.…”

Section: Stewart Ferguson Macdonald (1913–1998)mentioning

confidence: 99%

Paul Rothemund and S. Ferguson MacDonald, and their Namesake Reactions – The Influence of the Fischer School on my Life in Porphyrin Chemistry

Chang

2015

Israel Journal of Chemistry

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The Rothemund reaction and the MacDonald 2+2 condensation are two named reactions widely recognized in porphyrin syntheses. Yet not much has been written about the persons whose work paved the way to various porphyrins and porphyrinoids now realized. Paul Rothemund and S. Ferguson MacDonald both obtained their doctorate under Hans Fischer at Munich. Here I attempt to piece together the life stories of the two chemists, tracing back to the connections with the Fischer School, and giving the historical context to their namesake reactions. The pioneering discoveries of Fischer and his students, with later modifications, have become standard methods in the modern era for the synthesis of sizable quantities of porphyrins and porphyrinoids employed for enzyme models, catalysts, drugs, sensors, and building blocks of materials and biomedical research. This essay highlights the pioneers’ achievements, renders history relevant, and recounts the influence they had on my research.

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“…They are able to mimic the fundamental functions of the photosynthetic reaction centers, such as antenna function, stabilization of charge separation, sequential electron transfer (Boxer and Bucks, 1979;Wasielewski et al, 1982;Fujita et at., 1982;Calcaterra et at., 1983;Moore et al, 1984). Porphyrins or phthalocyanins, included in diads or triads, colinked or piled up, have been designed (Sakata et al, 1985;Seta et al, 1985;Abdalmuhdi and Chang, 1985;Dubowchik and Hamilton, 1986;Gaspard et al, 1986). In addition to their importance for the understanding of some key steps in natural photosynthesis, model molecules are increasingly attracting attention as precursors of components which could be used for technological applications in the field of molecular electronics (Aviram et a/., 1982;Joachim and Launay, 1984).…”

Section: Introductionmentioning

confidence: 99%

Stacked Zinc Triporphyrin as a Photoinduced Molecular Wire in Bilayers

Seta

Bienvenue

Maillard

et al. 1989

Photochem & Photobiology

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A molecule with three stacked zinc-porphyrin cycles and two basket-handles has been synthesized and incorporated into a bilayer lipid membrane. Under light excitation and in the presence of redox compounds in the aqueous phases bathing the membrane, this molecule induces a net electron flux across the membrane. The experimental variations of the flux with some external physicochemical parameters are accounted for by a tentative mechanism which relies on the ability of the porphyrin to act as an electron wire.

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A novel synthesis of triple-deckered triporphyrin

Abstract: The structure of the primary electron-donor-acceptor complex in reaction centers as well sis the molecular events involved in the electron-transport processes remain to be Scheme I

Cited by 56 publications

References 2 publications

Formation and optical properties of self-organized pentameric porphyrin arrays

Formation and optical properties of self-organized pentameric porphyrin arrays

Paul Rothemund and S. Ferguson MacDonald, and their Namesake Reactions – The Influence of the Fischer School on my Life in Porphyrin Chemistry

Stacked Zinc Triporphyrin as a Photoinduced Molecular Wire in Bilayers

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