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Poly(p-phenyleneethynylene)s by alkyne metathesis
1Department of Chemistry and Biochemistry, The University of South Carolina, Columbia, South Carolina 29208, USA. bunz@mail.chem.sc.edu
Accounts of Chemical Research
|December 19, 2001
Summary
Alkyne metathesis using molybdenum hexacarbonyl and phenols efficiently synthesizes diarylalkynes and high-molecular-weight polymers. This method enables the creation of advanced poly(phenylene ethynylene)s for organic electronics.
Area of Science:
- Organic Chemistry
- Polymer Chemistry
- Materials Science
Background:
- Alkyne metathesis is a powerful tool for carbon-carbon bond formation.
- Previous methods for alkyne metathesis had limitations in efficiency and scope.
- The synthesis of high-molecular-weight polymers is crucial for advanced materials applications.
Purpose of the Study:
- To improve the existing alkyne metathesis method using molybdenum hexacarbonyl and phenols.
- To explore the synthesis of diarylalkynes, alkyne-bridged macrocycles, and polymers.
- To develop high-molecular-weight poly[p-(dialkylphenylene)ethynylene]s (PPEs) for organic semiconductor devices.
Main Methods:
- Utilizing mixtures of molybdenum hexacarbonyl (Mo(CO)6) and phenols at elevated temperatures.
- Applying an improved alkyne metathesis protocol.
- Subjecting propynylated arenes to the optimized reaction conditions.
Main Results:
- Quantitative formation of diarylalkynes from propynylated arenes.
- Successful synthesis of alkyne-bridged macrocycles and high-molecular-weight polymers.
- Accessibility of high-molecular-weight poly[p-(dialkylphenylene)ethynylene]s (PPEs).
Conclusions:
- The improved alkyne metathesis offers an efficient route to valuable organic compounds.
- The synthesized PPEs demonstrate potential as active layers in organic semiconductor devices.
- This methodology expands the synthetic capabilities for creating functional polymers.