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Rhodanine-based Knoevenagel reaction and ring-opening polymerization for efficiently constructing multicyclic
Ze Zhang1, Xuan Nie1, Fei Wang2
1CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui, 230026, People's Republic of China.
Nature Communications
|July 23, 2020
Summary
Researchers developed a novel rhodanine chemistry for synthesizing complex cyclic polymers. This versatile approach enables easy access to diverse multicyclic polymer structures previously inaccessible.
Area of Science:
- Polymer Chemistry
- Organic Synthesis
Background:
- Cyclic polymers exhibit unique properties but their synthesis is challenging.
- Existing methods limit access to complex multicyclic polymer architectures.
Purpose of the Study:
- To develop a versatile synthetic strategy for complex cyclic polymers.
- To utilize rhodanine as a key building block for novel polymer structures.
Main Methods:
- Employing the Knoevenagel reaction with rhodanine and aldehydes.
- Utilizing rhodanine as an initiator for anionic ring-opening polymerization of thiirane.
- Synthesizing cyclic polythioethers.
Main Results:
- Rhodanine's methylene group is highly active in Knoevenagel reactions.
- Rhodanine effectively initiates ring-opening polymerization.
- Rhodanine chemistry allows incorporation into various polymer architectures (backbone, side chain, branched).
Conclusions:
- Rhodanine serves as a dual-functional molecule: a monomer and an initiator.
- This rhodanine-based chemistry provides facile access to complex multicyclic polymers.
- The strategy opens new avenues for designing advanced cyclic polymer materials.
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