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

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

    Research output: Contribution to journalArticlepeer-review

    11 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 - Feb 2009

    All Science Journal Classification (ASJC) codes

    • Chemistry(all)

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