Synthesis of two optically active V-shaped molecules: Investigating the correlation between the stacking angle and chiroptical properties

This study demonstrates the synthesis of two optically active V-shaped molecules using enantiopure pseudo-ortho- and pseudo-meta-disubstituted [2.2]paracyclophane as the chiral building blocks. Both consist of the same π-electron system (p-phenylene-ethynylene containing three benzenes) stacked at t...

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Bibliographic Details
Published inTetrahedron Vol. 138; pp. 133406 - 133411
Main Authors Matsumura, Kensei, Inoue, Ryo, Morisaki, Yasuhiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.05.2023
Elsevier
Subjects
Chemistry
Chemistry, Organic
Circularly polarized luminescence
Cyclophane
Physical Sciences
Planar chirality
Science & Technology
Planar chirality
Circularly polarized luminescence
Cyclophane
CIRCULARLY-POLARIZED LUMINESCENCE
FUNCTIONALIZATION
RESOLUTION
PROGRESS
PLANAR
DERIVATIVES
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Summary:This study demonstrates the synthesis of two optically active V-shaped molecules using enantiopure pseudo-ortho- and pseudo-meta-disubstituted [2.2]paracyclophane as the chiral building blocks. Both consist of the same π-electron system (p-phenylene-ethynylene containing three benzenes) stacked at the terminal benzene rings with stacking angles of 60° and 120°, respectively. The chiroptical properties, particularly the circularly polarized luminescence behavior, of the molecule with a stacking angle of 60° were better than those of its counterpart, and these results were confirmed via theoretical studies. A correlation exists between the chiroptical properties and stacking angle of emissive π-conjugated molecules. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133406