Journal
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
Volume 16, Issue 2, Pages 200-209Publisher
WORLD SCI PUBL CO INC
DOI: 10.1142/S1088424612004501
Keywords
triazene-porphyrins; spectroelectrochemistry; push-pull system
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Funding
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)
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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.
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