7,7,8,8-tetraaryl-o-quinodimethane stabilized by dibenzo annulation: A helical π-electron system that exhibits electrochromic and unique chiroptical Properties

Takanori Suzuki, Yuto Sakano, Tomohiro Iwai, Shinichi Iwashita, Youhei Miura, Ryo Katoono, Hidetoshi Kawai, Kenshu Fujiwara, Yasushi Tsuji, Takanori Fukushima

研究成果: Article査読

30 被引用数 (Scopus)

抄録

When two benzene rings are fused to a tetraaryl-o-quinodimethane skeleton, sterically hindered helical molecules 1 acquire a high thermodynamic stability. Because the tetraarylbutadiene subunit contains electron-donating alkoxy groups, 1 undergo reversible two-electron oxidation to 22+, which can be isolated as deeply colored stable salts. Intramolecular transfer of the point chirality (e.g., sec-butyl) on the aryl groups to helicity induces a diastereomeric preference in dications 2 b2+ and 2 c2+, which represents an efficient method for enhancing circular-dichroism signals. Thus, those redox pairs can serve as new electrochiroptical response systems. X-ray analysis of dication 22+ revealed π-π stacking interaction of the diarylmethylium moieties, which is also present in solution. The stacking geometry is the key contributor to the chirosolvatochromic response.

本文言語English
ページ(範囲)117-123
ページ数7
ジャーナルChemistry - A European Journal
19
1
DOI
出版ステータスPublished - 2013 1月 2
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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