FeCl3-Mediated Oxidative Spirocyclization of Difluorenylidene Diarylethanes Leading to Dispiro[fluorene-9,5′-indeno[2,1-a]indene-10′,9″-fluorene]s

Jian Zhao, Zhanqiang Xu, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto, Tienan Jin

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

A novel FeCl3-mediated oxidative spirocyclization for construction of a new class of di-spirolinked π-conjugated molecules, dispiro[fluorene-9,5′-indeno[2,1-a]indene-10′,9″-fluorene]s (DSFIIFs), has been reported. The combination of FeCl3 with FeO(OH) triggered an unprecedented double one-electron oxidation of difluorenylidene diarylethanes to afford the corresponding dispirocycles in high yields. The highest fluorescence quantum yield was up to 0.94 in solution. This protocol is also applicable to the synthesis of the non-spirolinked dihydroindenoindenes.

Original languageEnglish
Pages (from-to)259-263
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number1
DOIs
Publication statusPublished - 2016 Jan 4

Keywords

  • conjugation
  • fluorescence
  • materials science
  • oxidation
  • spirocompounds

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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