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Synthesis of Two Novel Optically Active #‐Shaped Cyclic Tetramers Based on Planar Chiral [2.2]Paracyclophanes

2022; Wiley; Volume: 29; Issue: 18 Linguagem: Inglês

10.1002/chem.202203533

1521-3765

Aoi Morisaki, Ryo Inoue, Yasuhiro Morisaki,

Luminescence and Fluorescent Materials

This study reports the synthesis of optically active cyclic tetramers comprising four stacked π-electron systems from two enantiomerically pure [2.2]paracyclophane compounds (bis-(para)-pseudo-ortho- and bis-(para)-pseudo-meta-tetrasubstituted [2.2]paracyclophane compounds). Depending on the combination of the absolute configurations of the planar chiral pseudo-ortho- and pseudo-meta-[2.2]paracyclophane units, the cyclic tetramers formed either parallel-#- or weave-#-structures. The optical and chiroptical properties of both structures were investigated experimentally and theoretically. In particular, the weave-#-shaped cyclic tetramer exhibited good chiroptical properties and emitted circularly polarized luminescence (CPL) with a high anisotropy factor (|glum | value of the order of 10-3 ) and a CPL brightness (BCPL ) higher than 100.