NOTE: Synthesis and Characterization of a Poly(acrylamide) with Pendant 1,4-piperazine-2,5-dione Moieties via Post-polymerization Cyclization

Abstract

A poly(acrylamide) was synthesized from N α -Boc-N ϵ -acrolyl-l-lysylglycine methyl ester via radical polymerization. This polymer typically had Mn ∼ 100,000 g/mol, Mw ∼ 300,000 g/mol, and a Tg of 93°C. Removal of Boc with TFA and cyclization with DABCO™ in DMSO at 65°C afforded a soluble piperazinedione-containing polymer that had a Tg of 157°C and thermal stability up to 300°C. These results demonstrate a viable and efficient synthetic route to piperazinedione-containing polyacrylamides of high molecular weight. Related polymers that incorporate substituted indane moieties could be useful high Tg materials for fabrication of LC and NLO devices.