5-(1-(4-phenyl)-3-(4-nitrophenyl)triazene)-10,15,20-triphenylporphyrin: a new triazene-porphyrin dye and its spectroelectrochemical properties


Autoria(s): Iglesias, Bernardo Almeida; Hoerner, Manfredo; Toma, Henrique Eisi; Araki, Koiti
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

21/10/2013

21/10/2013

2012

Resumo

The new triazene-porphyrin dye 5-(1-(4-phenyl)-3-(4-nitrophenyl)triazene)-10,15,20-triphenylporphyrin, encompassing a reactive protonated triazene moiety, was prepared starting from meso-tetraphenylporphyrin (H2TPP), first converting it to the 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin, then reducing to the 5-(4-aminophenyl)-10,15,20-tri(phenyl) porphyrin intermediate, and reacting with the diazonium salt of 4-nitroaniline; and characterized by spectroscopic and electrochemical methods. The absorption spectrum of the neutral species resembled the sum of H2TPP and of 1,3-bis(4-nitrophenyl) triazene spectrum, but the deprotonated anionic species showed more delocalized frontier orbitals, behaving as a push-pull system exhibiting triazenide-to-porphyrin charge-transfer transitions.

Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)

Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)

Identificador

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, HACKENSACK, v. 16, n. 2, supl. 1, Part 1, pp. 200-209, FEB, 2012

1088-4246

http://www.producao.usp.br/handle/BDPI/35211

10.1142/S1088424612004501

http://dx.doi.org/10.1142/S1088424612004501

Idioma(s)

eng

Publicador

WORLD SCI PUBL CO INC

HACKENSACK

Relação

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES

Direitos

closedAccess

Copyright WORLD SCI PUBL CO INC

Palavras-Chave #TRIAZENE-PORPHYRINS #SPECTROELECTROCHEMISTRY #PUSH-PULL SYSTEM #SPECTROSCOPY #BEHAVIOR #CHEMISTRY, MULTIDISCIPLINARY
Tipo

article

original article

publishedVersion