Synthesis of di-peri-dinaphthoporphyrins by PtCl2-mediated cyclization of quinodimethane-type porphyrins

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

doi:10.1002/anie.201601303

Synthesis of di-peri-dinaphthoporphyrins by PtCl₂-mediated cyclization of quinodimethane-type porphyrins

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Di-peri-dinaphthoporphyrins can be regarded as a key and common substructure of fused porphyrinoids. PtCl₂-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 PtCl₂-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 ¹H NMR, UV/Vis absorption, cyclic voltammetry, NICS calculations, and AICD plot.

Original language	English
Pages (from-to)	6305-6309
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	21
DOIs	https://doi.org/10.1002/anie.201601303
Publication status	Published - 2016 May 17

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201601303

Cite this

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title = "Synthesis of di-peri-dinaphthoporphyrins by PtCl2-mediated cyclization of quinodimethane-type porphyrins",

abstract = "Di-peri-dinaphthoporphyrins can be regarded as a key and common substructure of fused porphyrinoids. PtCl2-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 PtCl2-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 1H NMR, UV/Vis absorption, cyclic voltammetry, NICS calculations, and AICD plot.",

author = "Masataka Umetani and Koji Naoda and Takayuki Tanaka and Lee, {Seung Kyu} and Juwon Oh and Dongho Kim and Atsuhiro Osuka",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

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doi = "10.1002/anie.201601303",

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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

PY - 2016/5/17

Y1 - 2016/5/17

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AB - Di-peri-dinaphthoporphyrins can be regarded as a key and common substructure of fused porphyrinoids. PtCl2-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 PtCl2-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 1H NMR, UV/Vis absorption, cyclic voltammetry, NICS calculations, and AICD plot.

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