Mechanochromism, Twisted/Folded Structure Determination, and Derivatization of (<i>N</i>‐Phenylfluorenylidene)acridane

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  • Yutaka Matsuo
    Hefei National Laboratory for Physical Sciences at the Microscale University of Science and Technology of China 96 Jinzhai Road Hefei Anhui 230026 China
  • Ya Wang
    Hefei National Laboratory for Physical Sciences at the Microscale University of Science and Technology of China 96 Jinzhai Road Hefei Anhui 230026 China
  • Hiroshi Ueno
    School of Chemistry Northeast Normal University 5268 Renmin Street Changchun Jilin 130024 China
  • Takafumi Nakagawa
    Department of Mechanical Engineering School of Engineering The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-8656 Japan
  • Hiroshi Okada
    Department of Mechanical Engineering School of Engineering The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-8656 Japan

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<jats:title>Abstract</jats:title><jats:p>(N‐Phenylfluorenylidene)acridane (Ph‐FA) compounds with electron‐withdrawing and ‐donating substituents (H, MeO, Ph, NO<jats:sub>2</jats:sub>, Br, F) at the para position of the phenyl group were successfully synthesized by Barton–Kellogg reactions of <jats:italic>N</jats:italic>‐aryl thioacridones and diazofluorene. By using the substituent on the nitrogen atom to alter the electronic properties, both the folded and twisted conformers of <jats:italic>p</jats:italic>‐NO<jats:sub>2</jats:sub>‐C<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>‐FA could be crystallographically characterized, which enabled the charge transfer from the electron‐donating acridane moiety to the electron‐accepting fluorenylidene moiety to be understood. Ground‐state mechanochromism, thermochromism, vapochromism, and proton‐induced chromism were demonstrated between the folded and twisted conformations of the conformers. Protonation and chemical oxidation of Ph‐FA gave two stable acridinium compounds, namely, the fluorenylacridinium and acridinium radical cations. The present study will contribute to the development of functional dyes and organic semiconductors.</jats:p>

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