Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 65, Pages 14871-14877Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202003188
Keywords
[2.2]paracyclophane; axial chirality; circularly polarized luminescence; planar chirality; propeller chirality
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Funding
- Japan Society for the Promotion of Science [19H02792]
- Murata Science Foundation
- Research Foundation for the Electrotechnology of Chubu
- Grants-in-Aid for Scientific Research [19H02792] Funding Source: KAKEN
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Optically active X-shaped molecules based on the planar chiral [2.2]paracyclophane building block were prepared, in which di(methoxy)terphenyl units were stacked on the central benzene rings. At 25 degrees C, anisolyl rings freely rotate in solution, while in the crystal form, they are fixed by intramolecular CH-pi interactions, thereby leading to the expression of the axial chirality, i.e., propeller chirality was exhibited by the planar chiral [2.2]paracyclophane moiety. The X-shaped molecule exhibited good circularly polarized luminescence (CPL) profiles with moderate Phi(PL) and a large g(lum) value in the order of 10(-3) at 25 degrees C, in solution. In contrast, at -120 degrees C, dual CPL emission with opposite signs was observed. According to the theoretical studies, the rotary motion of the anisolyl units is suppressed in the excited states, and so emission from two isomers could be observed. These results demonstrate that the axial chirality was controlled by the planar chirality, leading ultimately to propeller chirality.
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