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Novel Method for the Preparation of Disulfide Polymers and Gels
7th Annual Student Colloquium
October 13, 2010
Novel Method for the Preparation of Disulfide Polymers and Gels
Presented by Emily Q. Rosenthal
Department of Polymer Science
University of Akron
Abstract
In recent years, sulfur chemistry has gained renewed attention because of the ubiquitous presence of disulfide bonds in biological systems. Thiol-disulfide interchange is a common and constant biological reaction which is critical to protein folding and cellular regulation.1 The ability to form and cleave disulfide bonds under mild reaction conditions presents a myriad of options in the synthesis of new biomaterials and in the development of biologically inspired synthetic processes. Thiols may be oxidized by oxygen alone, but the addition of a catalyst is necessary to achieve acceptable reaction rates.2-4 Here we present a new method to produce rubbery and semicrystalline linear polymers, and gels with unique properties.5 The results of the polymerization reactions serve as a benchmark for alternative, biological catalysts in the synthesis of disulfide polymers and gels.
1) Bindoli, A.; Rigobello, M.P.; Scutari, G.; Cabbiani, C.; Casini, A.; Messori, L. Thioredoxin reductase: A target for gold compounds acting as potential anticancer drugs. Coordination Chemistry Reviews, 2009, 253, 1692-1707.
2) Oae, S. Organic Sulfur Chemsitry: Structure and Mechanism. Ann Arbor, MI: CRC Press, 1991.
3) Choi, W.; Sanda, F.; Kihara, N.; Endo, T. A novel one-pot oxidation polymerization of dithiols obtained from bifuctional five-memvered cyclic dithocarbonates with amines. Journal of Polymer Science: Part A: Polymer Chemistry, 1998, 36, 79-84.
4) Garcia Ruano, J.L.; Parra, A.; Aleman, J. Efficient synthesis of disulfides by air oxidation of thiols under sonication. Green Chemistry, 2008, 10, 706-711.
5) Puskas, J.E.; Rosenthal, E.Q. New Method for the Synthesis of Poly(Disulfide) Polymers and Gels. UA Disclosure 2010.