Synthesis of porphyrin-2,3,12,13- and -2,3,7,8-tetraones: building blocks for the synthesis of extended porphyrin arrays

Crossley, Maxwell J.; Govenlock, Linda J.; Prashar, Jognandan K.

doi:10.1039/c39950002379

Cited by 110 publications

(99 citation statements)

References 2 publications

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“…Following the common acid catalyzed route to condense aromatic o -diamines with vicinal diketones [13], the zinc α-dione porphyrin derivative 3 [14] was reacted with the 2,3-diaminoporphyrin zinc complex 2 . Porphyrin 1 (Scheme 1) was synthesized and isolated according to literature procedures [11,12] and subsequently reduced with NaBH 4 , in the presence of Pd/C 10% wt, under nitrogen in a CH 2 Cl 2 /MeOH (10:1) solution.…”

Section: Resultsmentioning

confidence: 99%

β-Pyrazino-fused tetrarylporphyrins

et al. 2013

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Section: Resultsmentioning

confidence: 99%

β-Pyrazino-fused tetrarylporphyrins

et al. 2013

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“…The peripheral nitro substituents of porphyrins can be reduced to the corresponding amino derivatives using SnCl 2 /HCl [162], or with NaBH 4 and 10% Pd/C in methanol [163], and β-aminoporphyrins have been shown to undergo acylation, diazotization and various reactions with carbonyl compounds [164-167]. …”

Section: Porphyrin Functionalizationmentioning

confidence: 99%

Syntheses and Functionalizations of Porphyrin Macrocycles

Vicente¹,

Smith²

2014

COS

108

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Porphyrin macrocycles have been the subject of intense study in the last century because they are widely distributed in nature, usually as metal complexes of either iron or magnesium. As such, they serve as the prosthetic groups in a wide variety of primary metabolites, such as hemoglobins, myoglobins, cytochromes, catalases, peroxidases, chlorophylls, and bacteriochlorophylls; these compounds have multiple applications in materials science, biology and medicine. This article describes current methodology for preparation of simple, symmetrical model porphyrins, as well as more complex protocols for preparation of unsymmetrically substituted porphyrin macrocycles similar to those found in nature. The basic chemical reactivity of porphyrins and metalloporphyrin is also described, including electrophilic and nucleophilic reactions, oxidations, reductions, and metal-mediated cross-coupling reactions. Using the synthetic approaches and reactivity profiles presented, eventually almost any substituted porphyrin system can be prepared for applications in a variety of areas, including in catalysis, electron transport, model biological systems and therapeutics.

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“…The difference in rate of metallation of chlorin-like and bacteriochlorin-like rings was recognised and exploited in earlier work on the synthesis of extended porphyrins. 115 …”

Section: Resultsmentioning

confidence: 99%