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Issue 3, 2015
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Optically active cyclic compounds based on planar chiral [2.2]paracyclophane: extension of the conjugated systems and chiroptical properties

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Abstract

A series of optically active cyclic compounds based on the planar chiral tetrasubstituted [2.2]paracyclophane core were synthesized to obtain luminescent materials with excellent chiroptical properties in both the ground and excited states. The optical resolution of tetrasubstituted [2.2]paracyclophane was carried out using our previously reported method. The obtained cyclic compounds were composed of the optically active propeller-shaped structures created by the [2.2]paracyclophane core with p-phenylene–ethynylene moieties. The compounds exhibited good optical profiles, with a large molar extinction coefficient (ε) and photoluminescence quantum efficiency (Φlum). The emission occurred mainly from the propeller-shaped cyclic structures. This optically active higher-ordered structure provided chiroptical properties of high performance, such as a large specific rotation ([α]D) and molar ellipticity ([θ]) in the ground state and intense circularly polarized luminescence (CPL) with large dissymmetry factors (glum) in the excited state. The results suggest that planar chiral [2.2]paracyclophane-based optically active higher-ordered structures, such as the propeller-shaped cyclic structure, are promising scaffolds for obtaining CPL and that appropriate modifications can enhance the CPL characteristics.

Graphical abstract: Optically active cyclic compounds based on planar chiral [2.2]paracyclophane: extension of the conjugated systems and chiroptical properties

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Publication details

The article was received on 17 Oct 2014, accepted on 18 Nov 2014 and first published on 19 Nov 2014


Article type: Paper
DOI: 10.1039/C4TC02339K
Author version available: Download Author version (PDF)
Citation: J. Mater. Chem. C, 2015,3, 521-529
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    Optically active cyclic compounds based on planar chiral [2.2]paracyclophane: extension of the conjugated systems and chiroptical properties

    M. Gon, Y. Morisaki and Y. Chujo, J. Mater. Chem. C, 2015, 3, 521
    DOI: 10.1039/C4TC02339K

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