From Dynamic Chirality to Stable Enantiomers: Conformational Locking via Synergistic Methylation and Macrocyclization
Tianyan Chen1, Shenglong An1, Zhiyun Zhang1
1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Centre, Frontiers Science Center for Materiobiology and Dynamic Chemistry, East China University of Science & Technology, Shanghai, China.
Chempluschem
|May 21, 2026
Summary
Researchers developed a method to create stable chiral molecules using macrocyclization. This technique enhances chiral functional materials by improving emission properties and enabling efficient narrowband emission.
Area of Science:
- Organic Chemistry
- Materials Science
- Supramolecular Chemistry
Background:
- Dynamically chiral molecules often remain racemic due to low isomerization barriers, limiting their use in chiral functional materials.
- Developing methods to stabilize dynamic chirality is crucial for advancing chiral material applications.
Purpose of the Study:
- To develop a synergistic strategy combining steric methylation and macrocyclization to convert dynamic chirality into static chirality.
- To create stable, efficient chiral luminescent materials with enhanced optical properties.
Main Methods:
- Synthesized a macrocycle (P5P21) by embedding a dynamic chiral unit (DPP21) into a pillararene scaffold.
- Utilized structural analyses to confirm the spatial confinement effect of the pillararene on the dynamic unit.
- Investigated the impact of macrocyclic locking on conformational inversion barriers and photophysical properties.
Main Results:
- The macrocycle P5P21 exhibited significant chiroptical activity induced by a single methyl group due to conformational freezing.
- Achieved enhanced emission color purity with a narrowed photoluminescence full width at half maximum (FWHM) from 107 to 41 nm.
- Boosted the photoluminescence quantum yield (PLQY) from 13.1% to 42.7%, resulting in efficient narrowband emission at 371 nm.
Conclusions:
- Macrocyclic locking effectively transforms dynamic chirality into static chirality by increasing the configurational inversion barrier (>21 kcal/mol).
- The strategy significantly reduces excited-state reorganization energy, leading to narrowband emission.
- This provides a versatile design paradigm for stable and efficient chiral luminescent materials.
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