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J Org Chem. 2017 May 19;82(10):5242-5249. doi: 10.1021/acs.joc.7b00511. Epub 2017 Apr 27.

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

The Journal of organic chemistry

Hidetaka Nishimura, Kazuo Tanaka, Yasuhiro Morisaki, Yoshiki Chujo, Atsushi Wakamiya, Yasujiro Murata

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.

PMID: 28430441 DOI: 10.1021/acs.joc.7b00511

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

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