Self-similar chiral organic molecular cages

Self-similar chiral organic molecular cages

22 January 2024 | Zhen Wang, Qing-Pu Zhang, Fei Guo, Hui Ma, Zi-Hui Liang, Chang-Hai Yi, Chun Zhang, Chuan-Feng Chen
This study explores the evolution of organic molecular cages (OMCs) into higher-level chiral superstructures with self-similar properties. The researchers used 2D tri-bladed propeller-shaped triphenylbenzene as building blocks to synthesize a racemic 3D tri-bladed propeller-shaped helical molecular cage. This cage then served as a building block for the creation of two higher-level 3D tri-bladed chiral helical molecular cages, which exhibit multilayer sandwich structures and self-similarity at different levels. The higher-level cages display intramolecular self-shielding effects and exclusive chiral narcissistic self-sorting behaviors. Enantiomers of the higher-level cages can be interconverted by introducing an excess of corresponding chiral cyclohexanediamine. In the solid state, these cages self-assemble into L-helical or D-helical nanofibers, achieving a scale transformation of chiral characteristics from chiral atoms to microscopic and mesoscopic levels. The study highlights the potential of these advanced OMC-based superstructures for enhancing and expanding their functional properties.This study explores the evolution of organic molecular cages (OMCs) into higher-level chiral superstructures with self-similar properties. The researchers used 2D tri-bladed propeller-shaped triphenylbenzene as building blocks to synthesize a racemic 3D tri-bladed propeller-shaped helical molecular cage. This cage then served as a building block for the creation of two higher-level 3D tri-bladed chiral helical molecular cages, which exhibit multilayer sandwich structures and self-similarity at different levels. The higher-level cages display intramolecular self-shielding effects and exclusive chiral narcissistic self-sorting behaviors. Enantiomers of the higher-level cages can be interconverted by introducing an excess of corresponding chiral cyclohexanediamine. In the solid state, these cages self-assemble into L-helical or D-helical nanofibers, achieving a scale transformation of chiral characteristics from chiral atoms to microscopic and mesoscopic levels. The study highlights the potential of these advanced OMC-based superstructures for enhancing and expanding their functional properties.
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[slides and audio] Self-similar chiral organic molecular cages