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Oxygen-Bridged Diphenylnaphthylamine as a Scaffold for Full-Color Circularly Polarized Luminescent Materials.

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      Abstract

      An oxygen-bridged diphenylnaphthylamine with a helical shape was designed and synthesized as a key scaffold for circularly polarized luminescent (CPL) materials. The introduction of electron-withdrawing groups, such as formyl and 2,2-dicyanovinyl substituents at the naphthyl moiety in this skeleton effectively decreases the LUMO level and thus allows a tuning of the band gap. The prepared model compounds exhibit intense CPL signals with a dissymmetry factor (g value) of 10(-3) both in CH2Cl2 solutions and in the solid states. The emission colors of these derivatives are influenced both by the substituents as well as by solvent effects, covering the whole visible region from blue to deep red.

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      Affiliations
      [1 ] Institute for Chemical Research, Kyoto University , Uji, Kyoto 611-0011, Japan.
      [2 ] Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura , Nishikyo-ku, Kyoto 615-8510, Japan.
      [3 ] Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University , 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan.
      [4 ] Precursory Research for Embryonic Science and Technology (PRESTO) Japan Science and Technology Agency , 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.
      Journal
      J. Org. Chem.
      The Journal of organic chemistry
      American Chemical Society (ACS)
      1520-6904
      0022-3263
      May 19 2017
      : 82
      : 10
      28430441
      10.1021/acs.joc.7b00511

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