Synthesis of (Bio)‐Degradable Poly(β‐thioester)s via Amine Catalyzed Thiol−Ene Click Polymerization

Joke Vandenbergh; Kayte Ranieri; Tanja Junkers

doi:10.1002/macp.201200470

journal article Oct 22, 2012

Synthesis of (Bio)‐Degradable Poly(β‐thioester)s via Amine Catalyzed Thiol−Ene Click Polymerization

Joke Vandenbergh Kayte Ranieri Tanja Junkers

Macromolecular Chemistry and Physics Vol. 213 No. 24 pp. 2611-2617 · Wiley

View at Publisher Save 10.1002/macp.201200470

Abstract

AbstractThe well‐known thiol‐ene click reaction is used to polymerize dithiols and diacrylate monomers. Using catalytic amounts of hexylamine, poly(ester‐sulfide)s are synthesized via consecutive Michael additions between 1,4‐butanedithiol and 1,6‐hexanediol diacrylate. The molecular weight of the polymers is controlled by the stoichiometric balance of the reagents and by optimizing reaction time. Maximum conversion is achieved at close to 20 min at room temperature. Thermal characterization of the polymer shows a melting temperature of 53 °C and good thermal stability of up to 200 °C. The poly(β‐thioester) readily degrades when in contact with acetic acid or NaOH solutions, but also degradation under more biological relevant conditions is indicated by partial hydrolysis of the ester linkages in phosphate buffers.

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Metrics

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Citations

38

References

Details

Published: Oct 22, 2012
Vol/Issue: 213(24)
Pages: 2611-2617
License: View

Authors

School of Chemistry, Monash University, 19 Rainforest Walk, Clayton, VIC 3800, Australia

Cite This Article

Joke Vandenbergh, Kayte Ranieri, Tanja Junkers (2012). Synthesis of (Bio)‐Degradable Poly(β‐thioester)s via Amine Catalyzed Thiol−Ene Click Polymerization. Macromolecular Chemistry and Physics, 213(24), 2611-2617. https://doi.org/10.1002/macp.201200470

Synthesis of (Bio)‐Degradable Poly(β‐thioester)s via Amine Catalyzed Thiol−Ene Click Polymerization

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