A Versatile and Convenient Method for the Functionalization of Porphyrins

Didier, Amandine; Michaudet, Lydie; Ricard, David; Baveux-Chambenoît, Valérie; Richard, Philippe; Boitrel, Bernard

doi:10.1002/1099-0690(200105)2001:10<1927::aid-ejoc1917>3.0.co;2-5

Cited by 20 publications

(30 citation statements)

References 32 publications

(23 reference statements)

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“…To do so, we designed a series of ligands with preorganized straps allowing ester or carboxylic acid groups to hang above the N-core, with a possible chelate effect. Such structures were obtained by reacting diethyl malonate on several atropisomers (aaaa, abab, and aabb) of picket porphyrins [28,29]. The two ligands 3 and 4 bearing ester groups in their straps in the aabb and abab series have been first investigated for bismuth complexation (Fig.…”

Section: Resultsmentioning

confidence: 99%

The overhanging carboxylic acid strategy: an alternative route to the porphyrin core expansion/modification for the coordination of large metal ions

Gac

Boitrel

2012

J. Porphyrins Phthalocyanines

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This account summarizes how the binding properties of a regular porphyrin macrocycle for large cations can be significantly modified and even tuned when the surrounding skeleton delivers at least one carboxylic acid group close to the N -core. While kinetics of metal insertion are drastically improved, unique dinuclear species can be obtained with a possible control of the nuclearity. The first incorporation of an α-core emitter radioisotope of particular interest for cancer therapy was recently demonstrated. All in all, this overhanging carboxylic acid strategy can be regarded as an alternative to either expanded porphyrins for the coordination of large cations from groups 14–15 (PbII, BiIII) or contracted and isomeric porphyrins for the coordination of smaller cations from group 12 (HgII)

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Section: Resultsmentioning

confidence: 99%

The overhanging carboxylic acid strategy: an alternative route to the porphyrin core expansion/modification for the coordination of large metal ions

Gac

Boitrel

2012

J. Porphyrins Phthalocyanines

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“…Using proton NMR spectroscopy, we have been able to demonstrate the effective coordination of the nitrogen base to the metal in the porphyrin. For instance, by preparing the zinc complex of a porphyrin bearing the tailed 2-methylimidazole and by comparison with the chemical shifts of the free-base compound, the signals corresponding to the 2-methylimidazole are clearly downfield-shifted [16].…”

Section: Resultsmentioning

confidence: 99%

Tripodal and/or picket porphyrins to mimic the cytochrome c oxidase activity

Didier

Ricard

L’Her

et al. 2003

J. Porphyrins Phthalocyanines

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The efficiency of different series of tris-(2-aminoethyl)amine TREN-capped porphyrins as catalysts for the electroreduction of dioxygen has been studied after adsorption of the molecules at the surface of a graphite electrode. The influence of two structural features have been explored: the relative position of the two metals in the iron-copper bimetallic complexes and the nature of the benzyl groups of the tripod itself. These compounds have also been compared with picket porphyrins bearing aromatic amino functions, e.g. quinoline. The conclusions obtained in the case of TRENcapped catalysts cannot be extended to those bearing aromatic pickets.

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“…This second approach is based on a general and easy preparation of several types of strapped porphyrins in only two steps, starting from different 'U-shaped' acceptors, by acylation of three isomers of TAPP [22]. This methodology was shown particularly adapted to the preparation of various cation binding superstructures and can be regarded as a generalization of Chang's ligand appended reaction [23].…”

Section: Bis-strapped Porphyrinsmentioning

confidence: 99%

“…First, the two signals of H 7 are really different, one of them being strongly downfield-shifted to 6.97 ppm. This value compares well with the chemical shift of the same proton of the analogous free base porphyrin in the aaaa geometry for which the X-ray structure clearly showed that the two straps, located on the same side of the porphyrin and because of a reciprocal steric repulsion, were almost in vertical position [22]. Second, one doublet of the AB system corresponding to the benzylic protons is shielded down to À0.06 ppm, just like in 15Zn (Figure 9.11d).…”

Section: Bis-strapped Porphyrinsmentioning

confidence: 99%

Bismuth Complexes of Porphyrins and their Potential in Medical Applications

Boitrel

2010

Biological Chemistry of Arsenic, Antimony and Bismuth

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In the past, the major medical application of bismuth consisted of the treatment of gastric ulcers by ingestion of large quantities of bismuth citrate. More recently, the resurgence of interest for bismuth medical applications has been more oriented towards possible applications in radiotherapy, and particularly in alpha-radioimmunotherapy (Figure 9.1) [1]. As this specific application will be reviewed exhaustively in Chapter 13 of this book, we will only discuss the design, synthesis and coordination properties of bismuth porphyrin complexes in this chapter, assuming that the goals and limits of this peculiar application are known. However, we should keep in mind that both alpha-emitter isotopes of bismuth-212 and 213 exhibit a very short half life of 60 and 45 min respectively, as this radiochemical property directly implies fast kinetics formation of complexes. Even if this potential application is far from being achieved, this very basic requirement will guide the research for new bismuth porphyrins.From the coordination point of view, porphyrins are known to coordinate most of the metallic and pseudometallic elements, and metalloporphyrins with over 80 different central

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A Versatile and Convenient Method for the Functionalization of Porphyrins

Cited by 20 publications

References 32 publications

The overhanging carboxylic acid strategy: an alternative route to the porphyrin core expansion/modification for the coordination of large metal ions

The overhanging carboxylic acid strategy: an alternative route to the porphyrin core expansion/modification for the coordination of large metal ions

Tripodal and/or picket porphyrins to mimic the cytochrome c oxidase activity

Bismuth Complexes of Porphyrins and their Potential in Medical Applications

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