Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 14, Issue 10, Pages 1681-1685Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201801741
Keywords
[2; 2]paracyclophane; circularly polarized luminescence; fluorophores; higher-ordered structures; planar chirality
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [17H05165, 17H05148]
- Nagase Science Technology Foundation
- Grants-in-Aid for Scientific Research [17H05148, 17H05165] Funding Source: KAKEN
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Planar chiral building blocks based on 4,7,12,15-tetrasubstituted [2.2]paracyclophanes were obtained via a synthetic route involving an optical resolution step. Planar chiral enantiomers, comprising two fluorophores that were stacked to form a V-shaped higher-ordered structure, were synthesized from these building blocks. The V-shaped molecules emitted intense circularly polarized luminescence (CPL). Their chiroptical properties were compared with those of X-shaped molecules bearing the same two fluorophores stacked together. The CPL sign of the X-shaped molecule was opposite to that of the V-shaped molecule, which is supported by the theoretical results, indicating that the CPL sign can be controlled by the orientation of the stacked fluorophores.
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