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

Research output: Contribution to journalArticle

3 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)865-871
Number of pages7
JournalJournal of Macromolecular Science - Pure and Applied Chemistry
Volume45
Issue number10
DOIs
StatePublished - Oct 2008

Fingerprint

3,6-bis(5-chloro-2-piperidyl)-2,5-piperazinedione
Cyclization
Polyacrylates
Polymers
Polymerization
lysylglycine
Free radical polymerization
Dimethyl Sulfoxide
Esters
Thermodynamic stability
Molecular weight
Fabrication
piperazine

Keywords

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

ASJC Scopus subject areas

  • Polymers and Plastics
  • Materials Chemistry

Cite this

@article{58a017639efe43dcaa4877c1836e753d,
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}",
year = "2008",
month = "10",
doi = "10.1080/10601320802300842",
language = "English (US)",
volume = "45",
pages = "865--871",
journal = "Journal of Macromolecular Science - Pure and Applied Chemistry",
issn = "1060-1325",
publisher = "Taylor and Francis Ltd.",
number = "10",

}

TY - JOUR

T1 - NOTE

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

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)

UR - http://www.scopus.com/inward/record.url?scp=50549091247&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=50549091247&partnerID=8YFLogxK

U2 - 10.1080/10601320802300842

DO - 10.1080/10601320802300842

M3 - Article

AN - SCOPUS:50549091247

VL - 45

SP - 865

EP - 871

JO - Journal of Macromolecular Science - Pure and Applied Chemistry

JF - Journal of Macromolecular Science - Pure and Applied Chemistry

SN - 1060-1325

IS - 10

ER -