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 T_g 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 T_g 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 T_g materials for fabrication of LC and NLO devices.

Keywords:

• Poly(acrylamide)
• 1,4-piperazine-2,5-dione
• hydrogen bonding
• high T_g polymer

Acknowledgments

Financial support of this research from the Office of Naval Research through the Center for Advanced Multifunctional Nonlinear Optical Polymers and Molecular Assemblies and from the University of Arizona through the Materials Characterization Program is gratefully acknowledged.