Catalytic Enantioselective Synthesis and Switchable Chiroptical Property of Inherently Chiral Macrocycles
Shuo Tong, Jiangtao Li, Dong‐Dong Liang, Yan-E Zhang, Qi-Yun Feng, Xin Zhang, Jieping Zhu, Mei‐Xiang Wang
Abstract
We report herein a strategy to construct enantiopure inherently chiral macrocycles, ABCD-type heteracalix[4]aromatics, through a catalytic enantioselective intramolecular C–N bond forming reaction. A chiral ligand-palladium complex was found to efficiently induce the inherent chirality of molecules during the macrocyclization process with ee values up to >99%. The resulting ABCD-type heteracalix[4]aromatics displayed excellent and pH-triggered switchable electronic circular dichroism and circularly polarized luminescence properties.
Topics & Concepts
Enantiopure drugChemistryEnantioselective synthesisCircular dichroismChirality (physics)Intramolecular forceAxial chiralityCatalysisStereochemistryMoleculeLuminescenceCombinatorial chemistryPalladiumOrganic chemistryPhysicsQuantum mechanicsChiral symmetry breakingOptoelectronicsNambu–Jona-Lasinio modelQuarkSynthesis and Properties of Aromatic CompoundsAxial and Atropisomeric Chirality SynthesisLuminescence and Fluorescent Materials