Optically active triptycenes containing hexa-peri-hexabenzocoronene units

A pair of novel optically active triptycene-based molecules ((R,R)-1 and (S,S)-1) containing two hexabenzocoronene moieties were synthesized and their optical and chiroptical properties were investigated. Optically active 1 emitted preferred-handed circularly polarized light upon UV irradiation, wit...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019, Vol.55 (76), p.11386-11389
Main Authors: Wada, Yuya, Shinohara, Ken-Ichi, Ikai, Tomoyuki
Format: Article
Language:English
Subjects:
Circular polarization
Comparative studies
Crystallization
Crystallography
Luminescence
Optical activity
Optical properties
Polarized light
Rigid structures
Thermal analysis
Ultraviolet radiation
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Summary:A pair of novel optically active triptycene-based molecules ((R,R)-1 and (S,S)-1) containing two hexabenzocoronene moieties were synthesized and their optical and chiroptical properties were investigated. Optically active 1 emitted preferred-handed circularly polarized light upon UV irradiation, with the luminescence dissymmetry factors found to be approximately 1.0 × 10-3. Based on a comparative study using the analogous triptycene derivative with two hexaphenylbenzene units (2), which was the key precursor of 1, the ladder-type rigid structure with an asymmetrically bent geometry was important for optically active 1 to exhibit circularly polarized luminescence (CPL). We also showed that rac-1 undergoes conglomerate crystallization, which allowed CPL to be produced by a random selection of crystals prepared from rac-1.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc06025a