NOTE: Synthesis and characterization of a poly(acrylamide) with pendant 1,4-piperazine-2,5-dione moieties via post-polymerization cyclization

Jeffrey R. Hammaker; Eugene A. Mash

doi:10.1080/10601320802300842

NOTE: Synthesis and characterization of a poly(acrylamide) with pendant 1,4-piperazine-2,5-dione moieties via post-polymerization cyclization

Jeffrey R. Hammaker, Eugene A. Mash

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

A poly(acrylamide) was synthesized from N -Boc-N -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 93C. Removal of Boc with TFA and cyclization with DABCO in DMSO at 65C afforded a soluble piperazinedione- containing polymer that had a Tg of 157C and thermal stability up to 300C. 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.

Original language	English (US)
Pages (from-to)	865-871
Number of pages	7
Journal	Journal of Macromolecular Science, Part A: Pure and Applied Chemistry
Volume	45
Issue number	10
DOIs	https://doi.org/10.1080/10601320802300842
State	Published - Oct 2008

Keywords

1,4-piperazine-2,5-dione
High T polymer
Hydrogen bonding
Poly(acrylamide)

ASJC Scopus subject areas

Ceramics and Composites
General Chemistry
Polymers and Plastics
Materials Chemistry

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10.1080/10601320802300842

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title = "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 -Boc-N -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 93C. Removal of Boc with TFA and cyclization with DABCO in DMSO at 65C afforded a soluble piperazinedione- containing polymer that had a Tg of 157C and thermal stability up to 300C. 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.",

keywords = "1,4-piperazine-2,5-dione, High T polymer, Hydrogen bonding, Poly(acrylamide)",

author = "Hammaker, {Jeffrey R.} and Mash, {Eugene A.}",

note = "Funding Information: 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.",

year = "2008",

month = oct,

doi = "10.1080/10601320802300842",

language = "English (US)",

volume = "45",

pages = "865--871",

journal = "Journal of Macromolecular Science, Part A: Pure and Applied Chemistry",

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publisher = "Taylor and Francis Ltd.",

number = "10",

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T2 - Synthesis and characterization of a poly(acrylamide) with pendant 1,4-piperazine-2,5-dione moieties via post-polymerization cyclization

AU - Hammaker, Jeffrey R.

AU - Mash, Eugene A.

N1 - Funding Information: 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.

PY - 2008/10

Y1 - 2008/10

N2 - A poly(acrylamide) was synthesized from N -Boc-N -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 93C. Removal of Boc with TFA and cyclization with DABCO in DMSO at 65C afforded a soluble piperazinedione- containing polymer that had a Tg of 157C and thermal stability up to 300C. 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.

AB - A poly(acrylamide) was synthesized from N -Boc-N -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 93C. Removal of Boc with TFA and cyclization with DABCO in DMSO at 65C afforded a soluble piperazinedione- containing polymer that had a Tg of 157C and thermal stability up to 300C. 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.

KW - 1,4-piperazine-2,5-dione

KW - High T polymer

KW - Hydrogen bonding

KW - Poly(acrylamide)

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DO - 10.1080/10601320802300842

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SP - 865

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JO - Journal of Macromolecular Science, Part A: Pure and Applied Chemistry

JF - Journal of Macromolecular Science, Part A: Pure and Applied Chemistry

IS - 10

ER -

NOTE: Synthesis and characterization of a poly(acrylamide) with pendant 1,4-piperazine-2,5-dione moieties via post-polymerization cyclization

Abstract

Keywords

ASJC Scopus subject areas

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