Crystal structures and redox responses coupled with ion recognition of p-benzoquinone- And hydroquinone-fused [18]crown-6

Takayuki Kobayashi, Yuta Nakane, Takashi Takeda, Norihisa Hoshino, Hidetoshi Kawai, Tomoyuki Akutagawa

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The crystal structures and redox properties of p-benzoquinone (BQ)-fused [18]crown-6 1 and bis-BQ-fused [18]crown-6 2 were examined. The anion radicals of these BQ molecules were stabilized by addition of metal ions, through effective electrostatic interactions between the negatively charged BQ moiety and positively charged ion-capturing [18]crown-6 unit. The electrostatic interactions and solvation energy played important roles in determining the magnitudes of anodic redox shifts in the reduction potentials. Regular π-stacking of BQ units and regular arrays of [18]crown-6 units were observed in crystal 2, in which onedimensional π-electron columns were separated by ionic channels. The hydroquinone-fused [18]crown-6 molecule 3 and a new BQ- and phenol-fused [18]crown-6 derivative 4 were obtained as single crystals. The molecular conformations of [18]crown-6 in crystal 3 and hydrated crystal 3·H2O were different from each other.

Original languageEnglish
Pages (from-to)390-396
Number of pages7
JournalChemistry - An Asian Journal
Volume10
Issue number2
DOIs
Publication statusPublished - 2015 Feb

Keywords

  • Hydroquinone
  • Ion recognition
  • P-benzoquinone
  • Redox property
  • [18]crown-6

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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