Synthesis and characterization of 3‐aryl‐2‐(polystyryl)cyclopropenones via cyclopropenium ion substitution on polystyrene

C. H. Weidner, Timothy Edward Long

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Electrophilic substitution of cyclopropenium ions on aromatic polymers offers a unique opportunity to introduce polar functionality in a controlled manner to conventional, nonpolar polymers. Phenylcyclopropenone substituted polystyrene with predictable chemical composition and narrow molecular weight distribution were prepared. Size exclusion chromatography (SEC) analysis demonstrated the absence of branching or crosslinking in these functionalized polystyrenes during electrophilic substitution of the parent homopolymer. 13C‐NMR confirmed that the degree of phenylcyclopropenone substitution was both highly efficient and predictable over a broad compositional range. The glass transition temperature (Tg) of the polymers was found to vary linearly with mole % phenylcyclopropenone substitution of the polystyrene. Thermal gravimetric analysis (TGA) indicated that thermal decarbonylation of the appended cyclopropenones occurred at approximately 180°C. Weight loss vs. temperature profiles correlated reasonably well with levels of substitution based on 13C‐NMR analysis, confirming that decarbonylation of the calculated cyclopropenone substituents was the predominant thermal decomposition pathway. © 1995 John Wiley & Sons, Inc.

Original languageEnglish
Pages (from-to)1-6
Number of pages6
JournalJournal of Polymer Science Part A: Polymer Chemistry
Volume33
Issue number1
DOIs
Publication statusPublished - 1995 Jan 1
Externally publishedYes

Fingerprint

Polystyrenes
Substitution reactions
Ions
Polymers
Aromatic polymers
Size exclusion chromatography
Gravimetric analysis
Molecular weight distribution
Homopolymerization
Crosslinking
Pyrolysis
cyclopropenone
Chemical analysis
Temperature
Hot Temperature

Keywords

  • cyclopropenium
  • cyclopropenone
  • Friedel–Crafts
  • polymeric cyclopropenone
  • polystyrene
  • reactive oligomer
  • TGA

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Synthesis and characterization of 3‐aryl‐2‐(polystyryl)cyclopropenones via cyclopropenium ion substitution on polystyrene. / Weidner, C. H.; Long, Timothy Edward.

In: Journal of Polymer Science Part A: Polymer Chemistry, Vol. 33, No. 1, 01.01.1995, p. 1-6.

Research output: Contribution to journalArticle

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