Synthesis and characterization of novel azo-embedded N-confused tetraphenylporphyrin

Motoki Toganoh, Takayoshi Hihara, Kentaro Yonekura, Yuichi Ishikawa, Hiroyuki Furuta

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A unique class of azo porphyrin, 5,10,15,20-tetraphenyl-21-phenylazo-(2- aza-21-carbaporphyrin 1, in which an azophenyl group is embedded in N-confused porphyrin, was synthesized and characterized by 1H NMR, 13C NMR, UV-vis absorption, MS, and X-ray crystallographic analysis. Synthesis of 1 was achieved through a coupling reaction of 21-amino N-confused tetraphenylporphyrin with nitrosobenzene and subsequent deoxygenation of resulting azoxy derivative with a trioxo rhenium(VII) N-fused porphyrinato catalyst. The azo-conjugate molecule was exclusively obtained as a trans-isomer and no isomerization to the cis-isomer was observed under thermal or photoirradiation. The absorption spectrum of 1 shows a moderate red-shift due to the effective interaction between the porphyrinic π-system and the connecting azophenyl group. Upon protonation, this effect is essentially lost as a result of removing degeneracy of LUMO and LUMO+1.

Original languageEnglish
Pages (from-to)215-222
Number of pages8
JournalJournal of Porphyrins and Phthalocyanines
Volume13
Issue number2
DOIs
Publication statusPublished - Jan 1 2009

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Porphyrins
Isomers
Nuclear magnetic resonance
Rhenium
Protonation
Isomerization
Absorption spectra
Derivatives
X rays
Catalysts
Molecules
tetraphenylporphyrin
Hot Temperature
nitrosobenzene
5,10,15,20-tetraphenyl-21-phenylazo-2-aza-21-carbaporphyrin

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Synthesis and characterization of novel azo-embedded N-confused tetraphenylporphyrin. / Toganoh, Motoki; Hihara, Takayoshi; Yonekura, Kentaro; Ishikawa, Yuichi; Furuta, Hiroyuki.

In: Journal of Porphyrins and Phthalocyanines, Vol. 13, No. 2, 01.01.2009, p. 215-222.

Research output: Contribution to journalArticle

Toganoh, Motoki ; Hihara, Takayoshi ; Yonekura, Kentaro ; Ishikawa, Yuichi ; Furuta, Hiroyuki. / Synthesis and characterization of novel azo-embedded N-confused tetraphenylporphyrin. In: Journal of Porphyrins and Phthalocyanines. 2009 ; Vol. 13, No. 2. pp. 215-222.
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