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Porphyrin Synthesis by the “3+1” Approach: New Applications for an Old Methodology
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TLDR
The 3+1 approach has been used in the synthesis of new porphyrin structures, including tetrapyrrolic compounds with fused aromatic rings as mentioned in this paper, using other aromatic or unsaturated dialdehydes, including benzene-and pyridine-containing macrocycles.Abstract:
Acid-catalyzed condensation of tripyrranes with pyrrole-2,5-dicarboxaldehydes, followed by oxidation with an electron-deficient quinone, affords porphyrin products in excellent yields. This previously little used methodology has now been exploited in the synthesis of novel porphyrin structures, including tetrapyrrolic compounds with fused aromatic rings. By utilizing other aromatic or unsaturated dialdehydes, the “3+1” approach also allows the synthesis of new aromatic porphyrinoid systems, including benzene- and pyridine-containing macrocycles and carbaporphyrins.read more
Citations
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Porphyrin-based photosensitizers for use in photodynamic therapy
TL;DR: The history of the first generation PDT agent hematoporphyrin derivative is described in detail in this article, where the optical spectra of porphyrins and chlorins are analyzed.
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Synthetic routes to multiporphyrin arrays.
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Conjugated Macrocycles Related to the Porphyrins. 12.1 Oxybenzi- and Oxypyriporphyrins: Aromaticity and Conjugation in Highly Modified Porphyrinoid Structures
TL;DR: The 3 + 1 approach for porphyrinoid synthesis is an excellent methodology for preparing aromatic 6-membered ring subunit analogues as mentioned in this paper, and it has been shown to yield 35−52% yield.
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Recent Advances on the Synthesis and Chemistry of Carbaporphyrins and Related Porphyrinoid Systems
TL;DR: A wide spectrum of meso-unsubstituted porphyrin analogs have been synthesized using modified Lindsey-Rothemund reaction conditions, ranging from nonaromatic benziporphyrins to highly diatropic systems such as benzocarbaporphyrinoids as mentioned in this paper.
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The photophysical properties of expanded porphyrins: relationships between aromaticity, molecular geometry and non-linear optical properties
TL;DR: The main purpose of this article is to describe the structure-property relationships of a variety of expanded porphyrins based on experimental and theoretical results, which include steady-state and time-resolved spectroscopic characterizations, non-linear absorption ability and nucleus-independent chemical shift calculations.
References
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Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions
TL;DR: In this article, a new synthetic strategy for preparing tetraphenylporphyrins is presented, which should greatly expand synthetic entries into porphyrin-containing model systems, and is complementary to the Adler-Longo procedure.
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Investigation of the synthesis of ortho-substituted tetraphenylporphyrins
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A useful synthesis of pyrroles from nitroolefins
Derek H. R. Barton,Derek H. R. Barton,J. Kervagoret,J. Kervagoret,Samir Z. Zard,Samir Z. Zard +5 more
TL;DR: In this article, it was shown that β-acetoxy-nitro compounds react with α-isocyano-esters in the presence of an organic base to give pyrroles in good yield.
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