Journal article

Film-forming polymers containing in the main-chain dibenzo crown ethers with aliphatic (C₁₀−C₁₆), aliphatic−aromatic, or oxyindole spacers

  • Zolotukhin, Mikhail G. Instituto de Investigaciones en Materiales, Universidad Nacional Autonoma de Mexico, Mexico
  • Hernández, María del Carmen G. Instituto de Investigaciones en Materiales, Universidad Nacional Autonoma de Mexico, Mexico
  • Lopez, Ana Maria Instituto de Investigaciones en Materiales, Universidad Nacional Autonoma de Mexico, Mexico
  • Fomina, Loudmila Instituto de Investigaciones en Materiales, Universidad Nacional Autonoma de Mexico, Mexico
  • Cedillo, Gerardo Instituto de Investigaciones en Materiales, Universidad Nacional Autonoma de Mexico, Mexico
  • Nogales, Aurora Instituto de Estructura de la Materia, CSIC, Serrano 119, Madrid 28006, Spain
  • Ezquerra, Tiberio Instituto de Estructura de la Materia, CSIC, Serrano 119, Madrid 28006, Spain
  • Rueda, Daniel Instituto de Estructura de la Materia, CSIC, Serrano 119, Madrid 28006, Spain
  • Colquhoun, Howard M. School of Chemistry, University of Reading, Whiteknights, UK
  • Fromm, Katharina M. Department of Chemistry, University of Basel, Switzerland - Department of Chemistry, University of Fribopurg, Switzerland
  • Ruiz-Treviño, Alberto Universidad Iberoamericana, Departamento de Ingenierías, México
  • Ree, Moonhor Pohang University of Science and Technology, Hyoja-dong, Nam-gu Pohang, Korea
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    07.06.2006
Published in:
  • Macromolecules. - 2006, vol. 39, no. 14, p. 4696–4703
English Novel, linear, soluble, high-molecular-weight, film-forming polymers and copolymers in which main-chain crown ether units alternate with aliphatic (C₁₀−C₁₆) units have been obtained for the first time from aromatic electrophilic substitution reactions of crown ethers by aliphatic dicarboxylic acids followed by reduction of the carbonyl groups. The crown ether unit is dibenzo-18-crown-6, dibenzo-21-crown-7, dibenzo-24-crown-8, or dibenzo-30-crown-10; the aliphatic spacer is derived from a dicarboxylic acid (sebacic, 1,12-dodecanedicarboxylic, hexadecanedioic or 1,4-phenylenediacetic acids). The reactions were performed at 35 °C in a mixture of methanesulfonic acid (MSA) with phosphorus pentoxide, 12:1 (w/w), (Eaton's reagent). The carbonyl groups in the polyketones obtained were completely reduced to methylene linkages by treatment at room temperature with triethylsilane in a mixture of trifluoroacetic acid and dichloromethane. Polymers containing in the main chain crown ethers alternating with oxyindole fragments were prepared by one-pot condensation of crown ethers with isatin in a medium of Eaton's reagent. A possible reaction mechanism is suggested. According to IR and NMR analyses, the polyacylation reactions lead to the formation of isomeric (syn/anti-substituted) crown ether units in the main chain. The polymers obtained were soluble in the common organic solvents, and flexible transparent films could be cast from the solutions. DSC and X-ray studies of the polymers with “symmetrical” crown ethers reveal the presence of the endotherms corresponding to the supramolecular assemblies.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/300891
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