4.5 Article

Optically Active Cyclic Compounds Based on Planar Chiral [2.2]Paracyclophane with Naphthalene Units

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 5, Issue 3, Pages 353-359

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201500468

Keywords

[2; 2]paracyclophanes; circularly polarized luminescence; naphthalenes; planar chirality; photoluminescence

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan [15H00992]
  2. Japan Society for the Promotion of Science for Young Scientists [14J02514]
  3. Grants-in-Aid for Scientific Research [14J02514, 15H00992] Funding Source: KAKEN

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Two optically active cyclic compounds based on a planar chiral [2.2]paracyclophane core and containing either benzene or naphthalene moieties at the four corners of the structures were synthesized. Their optical and chiroptical properties were investigated by UV/vis absorption, photoluminescence (PL), circular dichroism, and circularly polarized luminescence (CPL) spectroscopy, as well as by density functional theory calculations. The circularly polarized luminescence (CPL) performance of the naphthalene-containing cyclic compound was high with a large molar extinction coefficient, good photoluminescence efficiency, and a good CPL dissymmetry factor.

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