Optically Active Triangle‐shaped Macrocycles Based on Planar Chiral [2.2]Paracyclophane

Abstract An optically active macrocycle containing an enantiopure pseudo‐ ortho ‐linked [2.2]paracyclophane skeleton was synthesized. This molecule consisted of a phenylene‐ethynylene‐typed π‐conjugation system, which was folded to construct a triangle‐shaped (one‐handed helical) structure. The extended π‐conjugation length derived from the single π‐conjugation system resulted in a large molar absorption coefficient and a good photoluminescence quantum efficiency. Intense circularly polarized luminescence (CPL) signals were observed, and the chiroptical properties were reproduced by the molecular simulations. The macrocycle was found to be a good CPL emitter with a high anisotropy factor and high CPL brightness values.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-03-11
DOI
https://doi.org/10.1002/ajoc.202500155
Citations
2
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
1.87
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article

Optically Active Triangle‐shaped Macrocycles Based on Planar Chiral [2.2]Paracyclophane

Ryo Inoue, Yasuhiro Morisaki, Yuki Fujita
2 citations
Asian Journal of Organic Chemistry
Synthesis and Properties of Aromatic Compounds
1.87
article

Optically Active Triangle‐shaped Macrocycles Based on Planar Chiral [2.2]Paracyclophane

Ryo Inoue, Yasuhiro Morisaki, Yuki Fujita
article en
2 citations

Abstract

Abstract An optically active macrocycle containing an enantiopure pseudo‐ ortho ‐linked [2.2]paracyclophane skeleton was synthesized. This molecule consisted of a phenylene‐ethynylene‐typed π‐conjugation system, which was folded to construct a triangle‐shaped (one‐handed helical) structure. The extended π‐conjugation length derived from the single π‐conjugation system resulted in a large molar absorption coefficient and a good photoluminescence quantum efficiency. Intense circularly polarized luminescence (CPL) signals were observed, and the chiroptical properties were reproduced by the molecular simulations. The macrocycle was found to be a good CPL emitter with a high anisotropy factor and high CPL brightness values.

Asian Journal of Organic ChemistryVol. 14(5)
University of Hyogo (JP), Kwansei Gakuin University (JP)
Openalex Percentile: Top 17%
Synthesis and Properties of Aromatic Compounds
1.87
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