Closed Pentaaza[9]helicene and Hexathia[9]/[5]helicene

Oxidative Fusion Reactions of ortho-Phenylene-Bridged Cyclic Hexapyrroles and Hexathiophenes

Fengkun Chen, Takayuki Tanaka, Yong Seok Hong, Tadashi Mori, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Oxidative fusion reactions of ortho-phenylene-bridged cyclic hexapyrroles and hexathiophenes furnished novel closed helicenes in a selective manner. X-Ray diffraction analysis unambiguously revealed the structures to be a closed pentaaza[9]helicene, the longest azahelicene reported so far, and an unexpected double-helical structure of hexathia[9]/[5]helicene, whose formation was assumed to result from multiple oxidative fusion along with a 1,2-aryl shift. The pentaaza[9]helicene exhibited well-defined emission with high fluorescence quantum yield (ΦF=0.31) among the known [9]helicenes. Chiral resolution of the racemic pentaaza[9]helicene and hexathia[9]/[5]helicene were achieved by chiral-phase HPLC and the enantiomers were characterized by circular dichroism spectra and DFT calculations.

Original languageEnglish
Pages (from-to)14688-14693
Number of pages6
JournalAngewandte Chemie - International Edition
Volume56
Issue number46
DOIs
Publication statusPublished - 2017 Nov 13

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Fusion reactions
Enantiomers
Dichroism
Quantum yield
Discrete Fourier transforms
X ray diffraction analysis
Fluorescence
helicenes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Chen, Fengkun ; Tanaka, Takayuki ; Hong, Yong Seok ; Mori, Tadashi ; Kim, Dongho ; Osuka, Atsuhiro. / Closed Pentaaza[9]helicene and Hexathia[9]/[5]helicene : Oxidative Fusion Reactions of ortho-Phenylene-Bridged Cyclic Hexapyrroles and Hexathiophenes. In: Angewandte Chemie - International Edition. 2017 ; Vol. 56, No. 46. pp. 14688-14693.
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Closed Pentaaza[9]helicene and Hexathia[9]/[5]helicene : Oxidative Fusion Reactions of ortho-Phenylene-Bridged Cyclic Hexapyrroles and Hexathiophenes. / Chen, Fengkun; Tanaka, Takayuki; Hong, Yong Seok; Mori, Tadashi; Kim, Dongho; Osuka, Atsuhiro.

In: Angewandte Chemie - International Edition, Vol. 56, No. 46, 13.11.2017, p. 14688-14693.

Research output: Contribution to journalArticle

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AU - Chen, Fengkun

AU - Tanaka, Takayuki

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AU - Mori, Tadashi

AU - Kim, Dongho

AU - Osuka, Atsuhiro

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Y1 - 2017/11/13

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