Journal
JOURNAL OF MATERIALS CHEMISTRY C
Volume 3, Issue 3, Pages 521-529Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4tc02339k
Keywords
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [24685018]
- Japan Society for the Promotion of Science [26-2514]
- Grants-in-Aid for Scientific Research [24685018, 14J02514] Funding Source: KAKEN
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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 (epsilon) and photoluminescence quantum efficiency (Phi(lum)). 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 ([alpha](D)) and molar ellipticity ([theta]) in the ground state and intense circularly polarized luminescence (CPL) with large dissymmetry factors (g(lum)) 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.
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