Synthesis of di-peri-dinaphthoporphyrins by PtCl 2 -mediated cyclization of quinodimethane-type porphyrins

Masataka Umetani, Koji Naoda, Takayuki Tanaka, Seung Kyu Lee, Juwon Oh, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Di-peri-dinaphthoporphyrins can be regarded as a key and common substructure of fused porphyrinoids. PtCl 2 -mediated cycloisomerization reaction of quinodimethane-type porphyrins provided these doubly fused porphyrins, which exhibit characteristic paratropic ring currents that presumably arise from 24 π antiaromatic circuit as a dominant resonance contributor. UV/Vis absorption spectra, cyclic voltammetry, and excited-state dynamics as well as theoretical calculation support this conclusion. The core of the matter: Di-peri-dinaphthoporphyrins have been synthesized by PtCl 2 -mediated cycloisomerization reaction of quinodimethane-type porphyrins. These porphyrins can be regarded as a key substructure of fused porphyrinoids, for which a 24π antiaromatic circuit was proven to be a dominant resonance contributor by 1 H NMR, UV/Vis absorption, cyclic voltammetry, NICS calculations, and AICD plot.

Original languageEnglish
Pages (from-to)6305-6309
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number21
DOIs
Publication statusPublished - 2016 May 17

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Cyclization
Porphyrins
Cyclic voltammetry
Networks (circuits)
Excited states
Absorption spectra
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Umetani, Masataka ; Naoda, Koji ; Tanaka, Takayuki ; Lee, Seung Kyu ; Oh, Juwon ; Kim, Dongho ; Osuka, Atsuhiro. / Synthesis of di-peri-dinaphthoporphyrins by PtCl 2 -mediated cyclization of quinodimethane-type porphyrins In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 21. pp. 6305-6309.
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Synthesis of di-peri-dinaphthoporphyrins by PtCl 2 -mediated cyclization of quinodimethane-type porphyrins . / Umetani, Masataka; Naoda, Koji; Tanaka, Takayuki; Lee, Seung Kyu; Oh, Juwon; Kim, Dongho; Osuka, Atsuhiro.

In: Angewandte Chemie - International Edition, Vol. 55, No. 21, 17.05.2016, p. 6305-6309.

Research output: Contribution to journalArticle

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AU - Umetani, Masataka

AU - Naoda, Koji

AU - Tanaka, Takayuki

AU - Lee, Seung Kyu

AU - Oh, Juwon

AU - Kim, Dongho

AU - Osuka, Atsuhiro

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