Synthesis, characterization and electrochemistry of bismuth porphyrins: X-ray crystal structure of (OEP)Bi(SO3CF3)

Michaudet, Lydie; Fasseur, D.; Guilard, Roger; Ou, Zhongping; Kadish, Karl M.; Dahaoui, Slimane; Lecomte, Claude

doi:10.1002/(sici)1099-1409(200004/05)4:3<261::aid-jpp203>3.0.co;2-b

Cited by 40 publications

(34 citation statements)

References 22 publications

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“…presentar ciertas desventajas, como son, velocidades de reacción lentas, rendimientos bajos y productos de baja pureza [1][2][3][4][5][6][7]. La electrosíntesis es una ruta alternativa para la obtención de metaloporfirinas.…”

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Electrochemical Metallization with Ni(II) from 5,10,15,20- Tetraquis(p-hydroxiphenyl)porfirin

Aguilera¹,

Blanco²,

Huerta³

et al. 2009

Port. Electrochim. Acta

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The electro-synthesis of a nickel metalloporphyrin by using the 5,10,15,20-tetraquis(phydroxyphenyl)porphyrin (TPPOH) as binding agent is reported. Before the electrosynthesis, cyclic voltammetry technique was applied to establish the best conditions for the electrochemical reduction of the porphyrin to the di-anion radical. The electrosynthesis of the metalloporphyrin was done under the conditions found from voltammetry. The electrolysis was performed in a non-divided cell, with a nickel sacrificial anode and at controlled potential, in order to favouring the chemical formation of the metal-complex by reaction between the porphyrin dianion radical and Ni(II) ions, both of them electro-generated during the process. The effect of the use of an ultrasonic wave of 20 kHz in the metalloporphyrin electro-synthesis process was studied. The porphyrin, of free base, and the products obtained in both the absence and the presence of ultrasonic were characterized through Atomic Absorption, UV-Visible, IR and elemental analysis. The results of this characterization make available to establish that the process leads to the formation of the metalloporphyrin of Ni(II) with TPPOH, with an electrolytic efficiency greater than 80%. The application of the 20 kHz ultrasonic wave at the amplitude of the study favoured the yield of the reaction and did not lead to changes in the electrochemical mechanism.Keywords: 5,10,15,20-tetraquis(p-hydroxyphenyl)porphyrin, nickel metalloporphyrins, electrosynthesis, sonic-electrochemistry, sonic-chemistry. IntroducciónLos primeros estudios acerca de las porfirinas y sus derivados, se han enfocado principalmente a la obtención de metaloporfirinas por vía química directa, haciendo reaccionar sales metálicas con las bases libres de las porfirinas. Este método de síntesis es el más utilizado para preparar metaloporfirinas, a pesar de * Corresponding author. E-mail address: leonyjerez@gmail.com E.N. Aguilera et al. / Port. Electrochim. Acta 27 (2009) 317-328 318 presentar ciertas desventajas, como son, velocidades de reacción lentas, rendimientos bajos y productos de baja pureza [1][2][3][4][5][6][7]. La electrosíntesis es una ruta alternativa para la obtención de metaloporfirinas. Las ventajas de la aplicación de esta técnica incluyen, entre otras: altos rendimientos, mayor pureza en los productos obtenidos, condiciones de reacción suaves, así como tiempos cortos de reacción. Sin embargo, esta técnica ha sido poco explotada y en muy pocos trabajos se ha reportado la obtención de metaloporfirinas por vía electroquímica [8][9]. En [10] se informa acerca de la electrosíntesis de un metalocomplejo de níquel con la 5,10,15,20-tetraquis(p-hidroxifenil)porfirina para modificar un electrodo de carbón vítreo, para su uso como sensor de contaminantes clorados. El proceso fue llevado a cabo en una celda no dividida, empleando acetonitrilo como disolvente y aplicando una corriente de 20 mA durante 15 minutos. Los resultados de la caracterización del producto obtenido, revelaron la formación de un...

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Electrochemical Metallization with Ni(II) from 5,10,15,20- Tetraquis(p-hydroxiphenyl)porfirin

Aguilera¹,

Blanco²,

Huerta³

et al. 2009

Port. Electrochim. Acta

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“…The first solid state structure of a bismuth porphyrin was reported by Guilard, Kadisk et al in 2000 [8]. In this work, either bismuth nitrate or bismuth triflate was used.…”

Section: The First X-ray Structure Of (Oep)bi(so 3 Cf 3 )mentioning

confidence: 95%

“…Reprinted with permission from[8]. Copyright(2000) Society of Porphyrins & Phthalocyanines potential oxygen atom donors, analogous of DOTA like compounds.…”

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confidence: 92%

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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“…This can be partly explained by the fact that cations such Tl(I), Pb(II), and Bi(III) possess a large ionic radius and are not expected to fit well in the porphyrin cavity but rather to exhibit an out-of-plane (OOP) coordination [3][4][5][6].…”

Section: Introductionmentioning

confidence: 98%

Structural analysis of a dimeric trinuclear zinc(II) complex based on a preorganized yet flexible strap porphyrin

Najjari

Roisnel

Boitrel

2017

J. Porphyrins Phthalocyanines

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ABSTRACT:We report the solid-state structure of an unexpected trinuclear zinc dimeric porphyrin complex resulting of zinc insertion into a single strap porphyrin. The latter bears an overhanging carboxylic acid which usually interacts with metal cations either in out-of-plane (OOP) or in hangingatop (HAT) coordination mode by changing its location above the porphyrin coordination site. However, in the present studies, the overhanging carboxylic group acts as a bidentate ligand and binds the OOPbound zinc cation together with another zinc cation bridging two porphyrin units. KEYWORDS:porphyrins, coordination, synthesis, X-ray diffraction, cation binding.

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Synthesis, characterization and electrochemistry of bismuth porphyrins: X-ray crystal structure of (OEP)Bi(SO₃CF₃)

Cited by 40 publications

References 22 publications

Electrochemical Metallization with Ni(II) from 5,10,15,20- Tetraquis(p-hydroxiphenyl)porfirin

Electrochemical Metallization with Ni(II) from 5,10,15,20- Tetraquis(p-hydroxiphenyl)porfirin

Bismuth Complexes of Porphyrins and their Potential in Medical Applications

Structural analysis of a dimeric trinuclear zinc(II) complex based on a preorganized yet flexible strap porphyrin

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