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Updated: Apr 28, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Harnessing Point-Planar Chirality Synergy: Crystallization-Enabled Resolution of Pillar[5]arene Rotaxanes With
Jie Lu1, Runjia Wang1, Peng Liu2
1Key Laboratory of Colloid, Interface and Chemical Thermodynamics Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing, P. R. China.
Abstract:
Immobilizing the planar chirality inherent to pillar[5]arene remains a challenge in supramolecular chemistry. Herein, we report a rational strategy for constructing chiral pillar[5]arene-based [2]rotaxanes and controlling their planar chirality by incorporating sterically bulky chiral stopper groups at both ends of the axle units. Using this approach, six structurally distinct [2]rotaxanes were efficiently resolved via simple recrystallization, achieving yields exceeding 90% and diastereomeric ratios (d.r.) above 99.5:0.5. These molecules can be classified as either synergistic or mismatched point-planar chiral [2]rotaxanes. Remarkably, only the synergistic point-planar chiral [2]rotaxanes exhibited tunable circularly polarized luminescence (CPL), with a maximum |glum| value of 0.02, whereas the mismatched configurations yielded no detectable CPL signal. This work overcomes a fundamental bottleneck in the scalable, stereocontrolled synthesis of chiral pillar[5]arene rotaxanes and establishes a robust platform for their development in chiroptical materials.
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