Planar Chiral [2.2]Paracyclophanes: Optical Resolution and Transformation to Optically Active π-Stacked Molecules

• Yasuhiro Morisaki

  Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337 , Japan

• Yoshiki Chujo

  Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510 , Japan

Abstract

In this article, our recent results from practical optical resolution methods of disubstituted and tetrasubstituted [2.2]paracyclophane compounds and their transformations are described. The obtained enantiopure [2.2]paracyclophane compounds have been used as chiral building blocks to prepare optically active π-stacked molecules. π-Stacked molecules construct optically active second-ordered structures, such as V-, N-, M-, X-, triangle-shaped, and one-handed double helical structures, due to the orientation of stacked π-electron systems. They emit circularly polarized luminescence (CPL) by photo-excitation. [2.2]Paracyclophane-based chiral π-stacked molecules in this article emit brightly owing to good photoluminescence (PL) quantum efficiencies as well as large molar extinction coefficients. In particular, emission is of course CPL with a large disymmetry factor (glum value). It is basically difficult to achieve CPL with high brightness, high PL efficiency, and large glum value by using other chiral scaffolds; therefore, planar chiral [2.2]paracyclophane is an ideal scaffold to be an excellent CPL emitters.

Journal

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 92 (2), 265-274, 2018-11-03

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360848661918093056
• NII Article ID: 130007591390
• DOI: 10.1246/bcsj.20180259
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/92/2/265/56298924/bcsj.20180259.pdf
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