An azulene-based chiral helicene and its air-stable cation radical

Masahiro Narita, Takaaki Teraoka, Toshihiro Murafuji, Yoshihito Shiota, Kazunari Yoshizawa, Shigeki Mori, Hidemitsu Uno, Shinji Kanegawa, Osamu Sato, Kenta Goto, Fumito Tani

Research output: Contribution to journalArticle

Abstract

A helicene compound called AIBTh, wherein two azulene units are fused with isobenzothiophene, has been prepared and characterized by spectroscopic and crystallographic methods. The enantiomers of AIBTh were resolved by HPLC, exhibiting stable optical activity. AIBTh showed two reversible oxidation and one irreversible reduction waves with a HOMO-LUMO gap of 2.07 eV. Upon one-electron oxidation of AIBTh, its air-stable cation radical was isolated and analyzed by EPR as well as X-ray crystallography. Based on the EPR spectrum, the crystal structure, and DFT calculation, it is suggested that favorable resonance structures including aromatic tropylium cation forms and wide delocalization of electronic spin are dominating in the electronic structure of the cation radical.

Original languageEnglish
Pages (from-to)1867-1873
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume92
Issue number11
DOIs
Publication statusPublished - Jan 1 2019

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Cations
Paramagnetic resonance
Air
Oxidation
Enantiomers
X ray crystallography
Discrete Fourier transforms
Electronic structure
Crystal structure
Electrons
azulene
tropylium

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

An azulene-based chiral helicene and its air-stable cation radical. / Narita, Masahiro; Teraoka, Takaaki; Murafuji, Toshihiro; Shiota, Yoshihito; Yoshizawa, Kazunari; Mori, Shigeki; Uno, Hidemitsu; Kanegawa, Shinji; Sato, Osamu; Goto, Kenta; Tani, Fumito.

In: Bulletin of the Chemical Society of Japan, Vol. 92, No. 11, 01.01.2019, p. 1867-1873.

Research output: Contribution to journalArticle

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AU - Yoshizawa, Kazunari

AU - Mori, Shigeki

AU - Uno, Hidemitsu

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AU - Goto, Kenta

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