Synthesis of a Tetrabenzotetraaza[8]circulene by a "fold-In" Oxidative Fusion Reaction

Fengkun Chen, Yong Seok Hong, Soji Shimizu, Dongho Kim, Takayuki Tanaka, Atsuhiro Osuka

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Abstract

Tetrabenzotetraaza[8]circulene (1) has been synthesized in good yield by a "fold-in" oxidative fusion reaction of a 1,2-phenylene-bridged cyclic tetrapyrrole. X-ray diffraction analysis of 1 has revealed a planar square structure with a central cyclooctatetraene (COT) core that shows little alternation of the bond lengths. Despite these structural features, 1 shows aromatic-like character, such as sharp absorption bands, high fluorescence quantum yields (ΦF=0.55 in THF), and a single exponential fluorescence decay with τF=3.8 ns. These observations indicate a dominant contribution of an [8]radialene-like π conjugation and hence aromatic character of the local aromatic segments in 1.

Original languageEnglish
Pages (from-to)10639-10642
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number36
DOIs
Publication statusPublished - Sep 1 2015

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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