Design and Synthesis of Internal-Edge-Substituted Helicenes

  • Usui Kazuteru
    Faculty of Pharmaceutical Sciences, Showa Pharmaceutical University

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  • ヘリセンのらせん構造内部空間に着目した機能性分子の創製研究
  • ヘリセン ノ ラセン コウゾウ ナイブ クウカン ニ チャクモク シタ キノウ ショウブンコ ノ ソウセイ ケンキュウ

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Abstract

<p>Helicenes are nonplanar 3D screw-shaped polycyclic compounds based on ortho-fused benzenes or aromatic rings, unlike other chiral compounds, and exhibit unique structural, optical, and electronic features. Thus, a large number of helicenes were investigated so far for a broad range of applications in study on chirality, catalysis, optoelectronics, and biology. In this study, a variety of carbo[5]helicenes with a substituent exclusively oriented toward the interior curvature of the helix are synthesiszed by PtCl2-catalyzed cycloisomerization. These[5]helicenes show a high enough configurationally stability. Based on this research, a series of novel optically active[5]helicene-derived phosphine ligands (L1, with a 7,8-dihydro[5]helicene core structure- and L2, with a fully aromatic[5]helicene core structure) were synthesized and applied to Pd-catalyzed asymmetric reactions. Furthermore, we recently designed and synthesized internal-edge-substituted coumarin-fused[6]helicenes with a phenyl substituent. Of particular note, the enantiomerically pure crystal adopted a one-dimensional columnar structure, which clearly showed the importance of the proper choice of a substituent for columnar arrangement.</p>

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