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Molecular Face-Rotating Cube with Emergent Chiral and Fluorescence Properties
Hang Qu1, Yu Wang1, Zhihao Li1
1State Key Laboratory of Physical Chemistry of Solid Surfaces, iChEM and College of Chemistry and Chemical Engineering, Xiamen University , Xiamen 361005, China.
Journal of the American Chemical Society
|August 26, 2017
Summary
Researchers created chiral organic cages using dynamic covalent chemistry and tetraphenylethylene (TPE). This method yields stable, fluorescent cages with emergent chirality, offering new possibilities for supramolecular assembly design.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Materials Science
Background:
- Chiral cage compounds typically rely on chiral precursors or symmetry breaking.
- Existing methods present limitations in controlling cage chirality.
- Tetraphenylethylene (TPE) is known for aggregation-induced emission properties.
Purpose of the Study:
- To develop a novel strategy for constructing chiral organic cages.
- To control the P or M rotational configuration of TPE faces.
- To investigate the origin of emergent chirality and fluorescence in these cages.
Main Methods:
- Dynamic covalent chemistry to restrict TPE rotational configurations.
- Graph theory for rational design and understanding cage assembly.
- Experimental characterizations (e.g., NMR, X-ray crystallography) and theoretical calculations.
- Spectroscopic techniques to study fluorescence and circularly polarized luminescence.
Main Results:
- Successfully constructed chiral organic cages by controlling TPE face configurations.
- Demonstrated emergent chirality arising from complex arrangements of TPE faces.
- Observed strong fluorescence and circularly polarized luminescence in the cages.
- Confirmed the stability of chirality and fluorescence due to restricted phenyl ring flipping.
Conclusions:
- A new method for constructing chiral organic cages using TPE and dynamic covalent chemistry has been established.
- The study elucidates the origin of emergent chirality and fluorescence in these supramolecular structures.
- The findings provide a rational design approach for chiral cages and related materials from aggregation-induced emission building blocks.
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