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Issue 14, 2009
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Dynamic polythioesters viaring-opening polymerization of 1,4-thiazine-2,5-diones

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Abstract

We describe the preparation and characterization of polythioesters composed of alternating α-amino acid and α-thioglycolic acid residues that undergo dynamic constitutional exchange under mild conditions. The polymers are assembled via reversible ring-opening polymerizations of 1,4-thiazine-2,5-diones and related monomers in solution-phase conditions that do not require the use of transition metal catalysts. Because 1,4-thiazine-2,5-diones can be derived in part from α-amino acids, a variety of side chain functionalized monomers in optically pure forms could readily be accessed. In addition, the resulting polythioesters have the potential for intra- and inter-chain hydrogen bonding, which is known to impart materials properties to other previously studied polyamides. The studies reported here could be useful in advancing a new class of biodegradable polymers and furthermore suggest that dynamic constitutional exchange could be exploited to modify many known synthetic and natural polythioesters.

Graphical abstract: Dynamic polythioesters viaring-opening polymerization of 1,4-thiazine-2,5-diones

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Supplementary files

Article information


Submitted
20 Feb 2009
Accepted
29 Apr 2009
First published
08 Jun 2009

Org. Biomol. Chem., 2009,7, 2878-2884
Article type
Paper

Dynamic polythioesters viaring-opening polymerization of 1,4-thiazine-2,5-diones

Y. Ura, M. Al-Sayah, J. Montenegro, J. M. Beierle, L. J. Leman and M. R. Ghadiri, Org. Biomol. Chem., 2009, 7, 2878
DOI: 10.1039/B903612A

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