Functionalized and Degradable Polyphthalaldehyde Derivatives

J. Patrick Lutz, Oleg Davydovich, Matthew D. Hannigan, Jeffrey S Moore, Paul M. Zimmerman, Anne J. McNeil

Research output: Contribution to journalArticle

Abstract

Polymers that depolymerize back to monomers can be repeatedly chemically recycled, thereby reducing their environmental impact. Polyphthalaldehyde is a metastable polymer that can rapidly and quantitatively depolymerize due to its low ceiling temperature. However, the effect of substitution on the physical and chemical properties of polyphthalaldehyde derivatives has not been systematically studied. Herein, we investigate the cationic polymerization of seven o-phthalaldehyde derivatives and demonstrate that judicious choice of substituent results in materials with a wide range of ceiling temperatures (<-60 to 106 °C) and decomposition temperatures (109-196 °C). We anticipate that these new polymers and their derivatives will enable researchers to access degradable materials with tunable thermal, physical, and chemical properties.

Original languageEnglish (US)
Pages (from-to)14544-14548
Number of pages5
JournalJournal of the American Chemical Society
Volume141
Issue number37
DOIs
StatePublished - Sep 18 2019

Fingerprint

Polymers
polymer
Ceilings
Derivatives
Chemical properties
Temperature
chemical property
Physical properties
physical property
o-Phthalaldehyde
Cationic polymerization
polymerization
Polymerization
Environmental impact
substitution
Substitution reactions
environmental impact
Thermodynamic properties
Hot Temperature
Monomers

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Lutz, J. P., Davydovich, O., Hannigan, M. D., Moore, J. S., Zimmerman, P. M., & McNeil, A. J. (2019). Functionalized and Degradable Polyphthalaldehyde Derivatives. Journal of the American Chemical Society, 141(37), 14544-14548. https://doi.org/10.1021/jacs.9b07508

Functionalized and Degradable Polyphthalaldehyde Derivatives. / Lutz, J. Patrick; Davydovich, Oleg; Hannigan, Matthew D.; Moore, Jeffrey S; Zimmerman, Paul M.; McNeil, Anne J.

In: Journal of the American Chemical Society, Vol. 141, No. 37, 18.09.2019, p. 14544-14548.

Research output: Contribution to journalArticle

Lutz, JP, Davydovich, O, Hannigan, MD, Moore, JS, Zimmerman, PM & McNeil, AJ 2019, 'Functionalized and Degradable Polyphthalaldehyde Derivatives', Journal of the American Chemical Society, vol. 141, no. 37, pp. 14544-14548. https://doi.org/10.1021/jacs.9b07508
Lutz JP, Davydovich O, Hannigan MD, Moore JS, Zimmerman PM, McNeil AJ. Functionalized and Degradable Polyphthalaldehyde Derivatives. Journal of the American Chemical Society. 2019 Sep 18;141(37):14544-14548. https://doi.org/10.1021/jacs.9b07508
Lutz, J. Patrick ; Davydovich, Oleg ; Hannigan, Matthew D. ; Moore, Jeffrey S ; Zimmerman, Paul M. ; McNeil, Anne J. / Functionalized and Degradable Polyphthalaldehyde Derivatives. In: Journal of the American Chemical Society. 2019 ; Vol. 141, No. 37. pp. 14544-14548.
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