Charge-transfer piperazine-containing polymeric systems via ring-opening metathesis polymerization

Brandon S. Chance, Adel Mostafa, Anjali Nair, Chayanant Hongfa, Hassan S. Bazzi

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

This article describes the synthesis of piperazine-containing homopolymer systems via ring-opening metathesis polymerization (ROMP). These systems were subsequently used as electron donors in the formation of charge-transfer (CT) complexes. Using exo-N-(6-bromohexyl)-7-oxabicyclo[2.2. l]hept-5-ene-2,3- dicarboxamide as a starting material, monomers were synthesized to act as electron donors. The amine group at the "open" end of the piperazine was either left open or alkylated with various alkyl groups. The monomers' ability to act as electron donors and their polymerization rates were studied. After initial photometric titration studies using 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) as an electron acceptor proved that these monomers would act as electron donors, they were subsequently polymerized into homopolymers via ROMP. The experimental results showed that a methanol:chloroform mixed solvent system enhanced the rate of polymerization over a single solvent (chloroform.) system. Studies also showed that the alkylated piperazine-containing monomer had a faster rate of polymerization than the secondary piperazine monomer. These monomers were used to make piperazine-containing homopolymers via ROMP and the resulting polymers, like the monomers, also functioned as electron donors. Potential functions of these polymers include electronics, solar cells, optical systems, and biological applications.

Original languageEnglish
Pages (from-to)5034-5043
Number of pages10
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume47
Issue number19
DOIs
Publication statusPublished - 1 Oct 2009

Fingerprint

Ring opening polymerization
Charge transfer
Monomers
Electrons
Homopolymerization
Polymerization
Chloroform
Chlorine compounds
Polymers
piperazine
Titration
Optical systems
Amines
Methanol
Solar cells
Electronic equipment

Keywords

  • Charge transfer
  • Metathesis
  • ROMP
  • Synthesis

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Charge-transfer piperazine-containing polymeric systems via ring-opening metathesis polymerization. / Chance, Brandon S.; Mostafa, Adel; Nair, Anjali; Hongfa, Chayanant; Bazzi, Hassan S.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 47, No. 19, 01.10.2009, p. 5034-5043.

Research output: Contribution to journalArticle

Chance, Brandon S. ; Mostafa, Adel ; Nair, Anjali ; Hongfa, Chayanant ; Bazzi, Hassan S. / Charge-transfer piperazine-containing polymeric systems via ring-opening metathesis polymerization. In: Journal of Polymer Science, Part A: Polymer Chemistry. 2009 ; Vol. 47, No. 19. pp. 5034-5043.
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