論文

2012年10月

Retro-Diels-Alder approach to the synthesis of π-expanded azuliporphyrins and their porphyrinoid aromaticity

Chemistry - A European Journal
  • Tetsuo Okujima
  • ,
  • Tasuku Kikkawa
  • ,
  • Haruyuki Nakano
  • ,
  • Hiroshi Kubota
  • ,
  • Nobumasa Fukugami
  • ,
  • Noboru Ono
  • ,
  • Hiroko Yamada
  • ,
  • Hidemitsu Uno

18
40
開始ページ
12854
終了ページ
12863
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1002/chem.201201399

Bicyclo[2.2.2]octadiene (BCOD) fused azuliporphyrins were synthesized by 3+1 porphyrin synthesis of azulitripyrranes with diformylpyrroles. Subsequent retro-Diels-Alder reaction of the BCOD-fused azuliporphyrins afforded azulibenzo-, azulidibenzo-, and azulitribenzoporphyrins 1-5. NMR and UV/Vis spectra, as well as nucleus-independent chemical shift (NICS) calculations revealed that 1-5 and their diprotonated dications exhibit relatively low porphyrinoid aromaticity, which was dependent on the position and number of fused benzene rings present. Porphyrins: A series of azulibenzoporphyrins were synthesized based on 3+1 porphyrin synthesis and retro-Diels-Alder reaction of bicyclo[2.2.2] octadiene-fused precursors (see scheme). UV/Vis spectra and NICS calculations revealed that their diprotonated dications exhibited a low porphyrinoid aromaticity from the porphyrinlike π circuit, which was dependent on the position and number of fused benzene rings. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

リンク情報
DOI
https://doi.org/10.1002/chem.201201399
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000309238400037&DestApp=WOS_CPL
URL
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84867043681&origin=inward
ID情報
  • DOI : 10.1002/chem.201201399
  • ISSN : 0947-6539
  • eISSN : 1521-3765
  • SCOPUS ID : 84867043681
  • Web of Science ID : WOS:000309238400037

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