論文

査読有り
2021年3月22日

A Robust Porphyrin‐Stabilized Triplet Carbon Diradical

Angewandte Chemie International Edition
  • Kaisheng Wang
  • Pingting Liu
  • Fenni Zhang
  • Ling Xu
  • Mingbo Zhou
  • Akito Nakai
  • Kenichi Kato
  • Ko Furukawa
  • Takayuki Tanaka
  • Atsuhiro Osuka
  • Jianxin Song
  • 全て表示

60
13
開始ページ
7002
終了ページ
7006
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1002/anie.202015356
出版者・発行元
Wiley

The synthesis of robust high-spin carbon radicals is an important topic in organic chemistry. Toward this end, several porphyrin-stabilized radicals have been systematically explored. A singly naphthalene-fused porphyrin radical was synthesized by a reaction sequence consisting of a Suzuki-Miyaura coupling of beta-borylated porphyrin with 2-bromobenzaldehyde, addition of mesityl Grignard reagent, intramolecular Friedel-Crafts alkylation, and final oxidation with DDQ or tBuOK/O-2. This strategy was also used to synthesize doubly naphthalene-fused porphyrins and syn- and anti-fused-anthracene-bridged porphyrin dimers. While singly naphthalene-fused porphyrin radical has been shown to be a stable monoradical, doubly naphthalene-fused porphyrins and anti-fused-anthracene-bridged porphyrin dimers have been shown to be closed-shell molecules. Finally, the syn-dimer was characterized as a surprisingly stable radical (t(1/2)=28 days under ambient air and at 80 degrees C) that is storable for more than several months, despite its high-spin triplet ground-state carbon diradical.

リンク情報
DOI
https://doi.org/10.1002/anie.202015356
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000621037100001&DestApp=WOS_CPL
URL
https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202015356
URL
https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.202015356
ID情報
  • DOI : 10.1002/anie.202015356
  • ISSN : 1433-7851
  • eISSN : 1521-3773
  • ORCIDのPut Code : 115597338
  • Web of Science ID : WOS:000621037100001

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