Syntheses, electrochemistry and photophysical properties of a series of meso-pyridylpentafluorophenylporphyrins


Autoria(s): MOREIRA, Emmanuel Z.; FERREIRA, Alba D. Q.; NERI, Claudio Roberto; MUKHOPADHYAY, Sumitra; DOVIDAUSKAS, Sergio; NIKOLAOU, Sofia; IAMAMOTO, Yassuko
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

19/10/2012

19/10/2012

2010

Resumo

This work presents the synthesis and characterization of a series of substituted pyridylpentafluroporphyrins, including the separation of the cis- and trans-isomers, the latter being characterized by X-ray crystallography. The spectroscopic and electrochemical properties of the series are dependent on the number of electron withdrawing pentafluorophenyl substituent, but they do not depend on the symmetry of the molecule. Ongoing from the monosubstituted to the more substituted pentafluorophenyl porphyrin H(2)(MPyTFPP) derivative, the Soret bands are slightly red-shifted and their quantum fluorescence yields range from 0.035 to 0.046, consistent with the value of 0.045 for the fully substituted 5,10,15,20-tetrapentafluorophenylporphyrin (dichloromethane solutions). The redox potentials of the reductive processes of monoanion and dianion formation are also sensitive to the number of pentafluoro substituents, shifting 180 mV to more positive values for the P(0)/P(-1) process ongoing from the monopentafluoro to the tris-pentafluorophenyl substituted derivative.

Brazilian agencies Fundacao de Amparo a Pesquisa do Estado de Sao Paulo FAPESP

FAPESP

Conselho Nacional de Desenvolvimento Cientifico e Tecnologico, CNPq

Identificador

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, v.14, n.11, p.975-984, 2010

1088-4246

http://producao.usp.br/handle/BDPI/20807

10.1142/S108842461000280X

http://dx.doi.org/10.1142/S108842461000280X

Idioma(s)

eng

Publicador

WORLD SCI PUBL CO INC

Relação

Journal of Porphyrins and Phthalocyanines

Direitos

restrictedAccess

Copyright WORLD SCI PUBL CO INC

Palavras-Chave #meso-pyridylpentafluorophenylporphyrins #spectroscopy #X-ray #isomerism #electrochemistry #PORPHYRIN-PYROMELLITIMIDE TRIADS #PI-PI INTERACTIONS #PHOTODYNAMIC THERAPY #ARTIFICIAL PHOTOSYNTHESIS #ELECTRON-TRANSFER #REACTION CENTERS #ENERGY-TRANSFER #SYSTEMS #DERIVATIVES #PYRIDYL #Chemistry, Multidisciplinary
Tipo

article

original article

publishedVersion