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DOI: 10.1055/s-0039-1691265
Synthesis of Chiral Triptycenes Containing Hexa-peri-hexabenzocoronene Units
Publication History
Publication Date:
18 November 2019 (online)
Significance
As a rigid, bulky and robust framework, triptycene has been incorporated into a variety of molecules. The unmodified triptycene is an achiral molecule but because it possesses substituents on the benzene rings it could be used to generate chiral molecules (Ikai et al. Org. Biomol. Chem. 2017, 15, 8440; Ikai et al. ACS Macro. Lett. 2018, 7, 364). The authors reported here the design and construction of a three-dimensional chiral molecule by combining the planar geometry of the hexa-peri-hexabenzocoronene and triptycene framework, which could emit circularly polarized light.
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Comment
The optically active triptycene-based molecule is synthesized through oxidative coupling. The molecule with rigid ladder geometry is separated by using chiral HPLC, and the resulting (R,R)-1 and (S,S)-1 can emit circularly polarized light because of the rigid chiral structure with limited conformation freedom, which is revealed by molecular modeling of the molecule. Moreover, the authors proved that optically active 1 could generate circularly polarized light without using other specialized instrument since 1 could be obtained through conglomerate crystallization.
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