A simplified synthesis for meso-tetraphenylporphine

Adler, Alan D.; Longo, Frederick R.; Finarelli, John D.; Goldmacher, Joel E.; Assour, Jacques M.; Korsakoff, Leonard

doi:10.1021/jo01288a053

Cited by 2,569 publications

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“…[20][21][22] This synthesis involves the condensation of pyrrole with 4-pyridinecarbaldehyde and pentafluorobenzaldehyde, under reflux for 30 min in acetic acid at 118 °C. Under such conditions, a mixture of porphyrin 1 and the desired porphyrin 2 were directly obtained.…”

Section: Synthesis and Characterization Of Porphyrinmentioning

confidence: 99%

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Maestrin¹,

Ribeiro²,

Tedesco³

et al. 2004

J. Braz. Chem. Soc.

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A terapia fotodinâmica (TFD) está baseada na administração e no acúmulo de fotossensibilizador, por exemplo, de tipo porfirina ou clorina, em tecidos doentes. As clorinas apresentam propriedades fotofísicas semelhantes àquelas das porfirinas, mas com intensificação e deslocamento das bandas Q, o que faz com que sejam bons candidatos para TFD. Neste trabalho relata-se a síntese da 5,10,15-tris(pentafluorofenil)-20-(4-piridil)porfirina, (2), e das clorinas isômeras 4, (5,10,20-tris(pentafluorofenil)-15-(4-piridil)-tetra-hidro-1H-N-metil-pirrolo[3,4-b]porfirina e 5, (5,10,15-tris(pentafluorofenil)-20-(4-piridil)-tetra-hidro-1H-N-metil-pirrolo[3,4-b]porfirina, obtidas a partir de 2, por reação de cicloadição 1,3-dipolar com um ileto azometínico, e respectivas caracterizações estruturais por UV-Vis, RMN e EM-FAB. Foram avaliadas as propriedades fotofísicas, fotoquímicas e fotodegradativas para a nova clorina 4, obtida com melhor rendimento que o seu isômero 5. O rendimento quântico de fotodegradação (φ Fd , mol Einstein -1 ) foi de 0,047±0,014. Foram ainda realizados testes com ácido úrico para demonstrar a capacidade do fotossensibilizador na produção de 1 O 2 . Os resultados mostraram que a nova clorina 4 pode ser considerada como um bom fotossensibilizador para TFD.Photodynamic therapy (PDT) is based on the accumulation of a photosensitizer, such as a porphyrin or a chlorin, in a malignant tissue after its administration. Chlorins exhibit photophysical properties similar to those of the porphyrin macrocycles, but with intensified and red-shifted Q bands, making chlorin-containing systems even better candidates for PDT. In this contribution, we report the synthesis of 5,10,15-tris(pentafluorophenyl)-20-(4-pyridyl)porphyrin, (2) and its transformation to the novel chlorin derivatives 4, (5,10,20-tris(pentafluorophenyl)-15-(4-pyridyl)-tetrahydro-1H-N-methyl-pyrrolo [3,4-b]porphyrin and 5, (5,10,15-tris(pentafluorophenyl)-20-(4-pyridyl)-tetrahydro-1H-N-methyl-pyrrolo[3,4-b]porphyrin) by 1,3-dipolar cycloaddition with an azomethine ylide. The new products have been characterized by UV-Vis, 1 H NMR and FAB-MS. The photophysics, photochemical and photobleaching properties of chlorin 4 have been evaluated. Its quantum yield of photobleaching (φ Pb , mol Einstein -1 ) was 0.047±0.014. In order to demonstrate the production of 1 O 2 when 4 is used as a photosensitizer, uric acid tests have been carried out. The results indicate that chlorin 4 can be considered a promising photosensitizer in PDT.

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Section: Synthesis and Characterization Of Porphyrinmentioning

confidence: 99%

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Maestrin¹,

Ribeiro²,

Tedesco³

et al. 2004

J. Braz. Chem. Soc.

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“…The porphyrins used in this study were prepared by published protocols. [35][36][37] Zinc(ii) 5,10,15,20-tetraphenylporphyrin (ZnTPP) and zinc(ii) 5,15-bis(4-carboxyphenyl)-10,20-diphenylporphyrin (ZnDCPP) were evaporated from a molecular evaporator at 275 • C and 350 • C, respectively. For the AFM investigation, the molecules were deposited to the substrate at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Thermally induced anchoring of a zinc-carboxyphenylporphyrin on rutile TiO2 (110)

Jöhr

Hinaut

Pawlak

et al. 2017

The Journal of Chemical Physics

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Functionalization of surfaces has become of high interest for a wealth of applications such as sensors, hybrid photovoltaics, catalysis, and molecular electronics. Thereby molecule-surface interactions are of crucial importance for the understanding of interface properties. An especially relevant point is the anchoring of molecules to surfaces. In this work, we analyze this process for a zinc-porphyrin equipped with carboxylic acid anchoring groups on rutile TiO2 (110) using scanning probe microscopy. After evaporation, the porphyrins are not covalently bound to the surface. Upon annealing, the carboxylic acid anchors undergo deprotonation and bind to surface titanium atoms. The formation of covalent bonds is evident from the changed stability of the molecule on the surface as well as the adsorption configuration. Annealed porphyrins are rotated by 45° and adopt another adsorption site. The influence of binding on electronic coupling with the surface is investigated using photoelectron spectroscopy. The observed shifts of Zn 2p and N 1s levels to higher binding energies indicate charging of the porphyrin core, which is accompanied by a deformation of the macrocycle due to a strong interaction with the surface.

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“…25 These results of the photoreduction of Zn phylloerythrin (35) were interpreted from by-product analysis and 2 H incorporation studies 310,82 as the primary formation of two isomeric porphodimethenes (36a,b) (A RAAX = 515 nm). These can subsequently isomerize in a dark (or light 25 ) reaction into the c/5-chlorin (37a), or are partially reoxidized into the porphyrin (35). The isomer 36a also undergoes a reaction in which ring Ε is opened to form a rhodochlorin 31b (Section II, B, 2).…”

Section: Metalloporphyrins To Metallochlorinsmentioning

confidence: 97%

“…The mechanism of hydroporphyrin formation during the synthesis of TPP has been studied by several groups. 7,8,35,36 It could be shown that the initially formed TPP-porphinogen is oxidized in an acid-catalyzed reaction to the porphyrin via a porphodimethene 37 intermediate. 8 The chlorin is then formed by the subsequent re-reduction of the porphyrin.…”

Section: Chemical Reduction To Chlorinsmentioning

confidence: 99%

Synthesis and Stereochemistry of Hydroporphyrins

Scheer¹

1978

The Porphyrins

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A simplified synthesis for meso-tetraphenylporphine

Cited by 2,569 publications

References 0 publications

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Thermally induced anchoring of a zinc-carboxyphenylporphyrin on rutile TiO2 (110)

Synthesis and Stereochemistry of Hydroporphyrins

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