Saucer[<i>n</i>]arenes: Synthesis, Structure, Complexation, and Guest‐Induced Circularly Polarized Luminescence Property

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  • Jing Li
    Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China
  • He‐Ye Zhou
    Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China
  • Ying Han
    Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China
  • Chuan‐Feng Chen
    Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China

説明

<jats:title>Abstract</jats:title><jats:p>Macrocycles denoted as saucer[n]arenes (n=4,5) were easily synthesized by the one‐pot condensation of 2,7‐dimethoxynaphthalene (2,7‐DMN) and paraformaldehyde in the presence of TFA or catalytic BF<jats:sub>3</jats:sub>⋅OEt<jats:sub>2</jats:sub>. With 1,1‐dimethylpiperidin‐1‐ium as the template, saucer[4]arene was selectively obtained. Crystal structures show that saucer[n]arenes are all composed of 2,7‐DMN moiety bridged by the methylene groups at 1,6‐positions: all of the 7‐methoxy groups lie on one face, and all of the 2‐methoxy groups lie on the other. Saucer[n]arenes exhibit strong fluorescence properties with the quantum yields of 19.6 % and 23.4 %. They form 1:1 complexes with ammonium salts in both solution and solid state (association constant up to 10<jats:sup>5</jats:sup> M<jats:sup>−1</jats:sup> in CDCl<jats:sub>3</jats:sub>). Chiral quaternary ammonium salts can induce the chirality of the dynamically racemic inherently chiral saucer[n]arenes in solution, and thus show mirror‐imaged circular dichroism signals and circularly polarized luminescence (CPL) properties.</jats:p>

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