Effect of Substitution Pattern of <i>tert</i>‐Butyl Groups in a Bisbenzofuropyrazine Core π‐System on Optical Properties: Unique Mechanochromic Fluorescence Behavior

DOI Web Site Web Site 被引用文献7件 参考文献56件
  • Shotaro Nakamura
    Department of Applied Chemistry Graduate School of Engineering, Osaka University Suita Osaka 565-0871 Japan
  • Norimitsu Tohnai
    Department of Material and Life Science Graduate School of Engineering, Osaka University Suita Osaka 565-0871 Japan
  • Yuji Nishii
    Frontier Research Base for Global Young Researchers Graduate School of Engineering Suita Osaka 565-0871 Japan
  • Tomoaki Hinoue
    Department of Applied Chemistry Graduate School of Engineering, Osaka University Suita Osaka 565-0871 Japan
  • Masahiro Miura
    Department of Applied Chemistry Graduate School of Engineering, Osaka University Suita Osaka 565-0871 Japan

書誌事項

公開日
2018-10-25
資源種別
journal article
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/cptc.201800189
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Bisbenzofuro[2,3‐<jats:italic>b</jats:italic> : 2′,3′‐<jats:italic>e</jats:italic>]pyrazine (BBFPy) and its 2,8‐ and 3,9‐di(<jats:italic>tert</jats:italic>‐butyl)‐substituted derivatives (<jats:bold>2 a</jats:bold> and <jats:bold>2 b</jats:bold>) were synthesized by palladium‐catalyzed intramolecular direct arylation as the key step. The effect of introduction of two <jats:italic>tert</jats:italic>‐butyl groups to the BBFPy core at the different positions on the fluorescent properties was then investigated. The <jats:italic>tert</jats:italic>‐butyl groups not only enhance the tractability with increasing solubility, but also induce different crystal‐packing patterns as anticipated. The compounds <jats:bold>2 a</jats:bold> and <jats:bold>2 b</jats:bold> show relatively strong blue fluorescence in both the solution and solid state. The 2,8‐isomer <jats:bold>2 a</jats:bold> specifically exhibits a unique mechanochromism in the solid state; <jats:bold>2 a</jats:bold> exhibits two crystalline forms, both of which show green fluorescence by grinding, while different self‐recovering fluorescence patterns between them are observed by standing. The intriguing mechanochromism is rationally interpreted in terms of molecular arrangements determined by X‐ray crystallography.</jats:p>

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