Selective Synthesis of Poly(m-phenylene oxides) over Oxacalixarenes
| Autor: | Jay Wm. Wackerly, W. Christian Crannell, Joseph M. Meyer, Jeffrey L. Katz, Sarah B. King |
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| Rok vydání: | 2009 |
| Předmět: |
Polymers and Plastics
Intramolecular reaction Organic Chemistry Side reaction Inorganic Chemistry chemistry.chemical_compound Monomer chemistry Phenylene Nucleophilic aromatic substitution Electrophile Polymer chemistry Materials Chemistry Nucleophilic substitution Organic chemistry Thermal stability |
| Zdroj: | Macromolecules. 42:8181-8186 |
| ISSN: | 1520-5835 0024-9297 |
| DOI: | 10.1021/ma901518w |
| Popis: | We report a high yielding AA−BB type step-growth synthesis of poly(m-phenylene oxides) (mPOs) by nucleophilic aromatic substitution (SNAr) reactions. Previously, poly(mPOs) have proven difficult to synthesize, especially by SNAr, due to competing cyclooligomer (oxacalixarene) formation. We have found that the linear (polymeric) vs cyclic (oligomeric) product distribution is strongly dependent on the substitution pattern of the electrophilic monomer, and a model is described that predicts whether the reacting monomers will kinetically favor formation of poly(mPOs) or oxacalixarenes. The polycondensation reaction tolerates a range of functional groups on both reactive monomers, and the synthesized poly(mPOs) have high thermal and aqueous stability but are readily depolymerized in polar aprotic media. |
| Databáze: | OpenAIRE |
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