New Types of Planar Chiral [2.2]Paracyclophanes and Construction of One-Handed Double Helices

Yasuhiro Morisaki; Risa Sawada; Masayuki Gon; Yoshiki Chujo

doi:10.1002/asia.201601028

New Types of Planar Chiral [2.2]Paracyclophanes and Construction of One-Handed Double Helices

Chem Asian J. 2016 Sep 20;11(18):2524-7. doi: 10.1002/asia.201601028. Epub 2016 Aug 16.

Authors

Yasuhiro Morisaki^{1

2}, Risa Sawada³, Masayuki Gon³, Yoshiki Chujo⁴

Affiliations

¹ Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan. ymo@kwansei.ac.jp.
² Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan. ymo@kwansei.ac.jp.
³ Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.
⁴ Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan. chujo@chujo.synchem.kyoto-u.ac.jp.

PMID: 27469202
DOI: 10.1002/asia.201601028

Abstract

New types of planar chiral (Rp )- and (Sp )-4,7,12,15-tetrasubstituted [2.2]paracyclophanes were synthesized from racemic 4,12-dihydroxy[2.2]paracyclophane as the starting compound. Regioselective dibromination and transformation afforded a series of planar chiral (Rp )- and (Sp )-4,7,12,15-tetrasubstituted [2.2]paracyclophanes, which can be used as chiral building blocks. In this study, left- and right-handed double helical structures were constructed via chemoselective Sonogashira-Hagihara coupling. The double helical compounds were excellent circularly polarized luminescence (CPL) emitters with large molar extinction coefficients, good photoluminescence quantum efficiencies, and large CPL dissymmetry factors.

Keywords: [2.2]paracyclophane; circularly polarized luminescence; double helices; planar chirality.