Polymers containing sulfonate ester groups in the main chain have been synthesized by Acyclic Diene Metathesis (ADMET) polymerization. Although traditional polyesters are one of the most ubiquitous classes of organic polymers, there are little to no reports of poly(sulfonate esters) in the literature. ADMET polymerization has proved to be an efficient technique for the synthesis of well-defined long-chain polyesters, and yet use of a sulfonate ester-containing monomer to that end has never been reported. The long-chain sulfonate ester-containing a,?-diene monomer (m = 9) necessary to evade the negative neighboring group effect (NNGE) and formation of cyclic oligomers was synthesized with the aid of a microwave reactor. This monomer was then polymerized using ruthenium alkylidene catalyst to yield polymers with molecular weights around 29,000 g/mol and polydispersities in the expected range for polycondensation. The conditions for polymerization have been optimized and the properties of the resulting poly(sulfonate esters) are reported herein. This work expands the library of monomers available for ADMET polymerization and results in a new category of degradable polymers.

Synthesis of poly(sulfonate ester)s by ADMET polymerization

247th National Meeting (2014)

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