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 language | English |
|---|---|
| Pages (from-to) | 1-6 |
| Number of pages | 6 |
| Journal | Journal of Polymer Science Part A: Polymer Chemistry |
| Volume | 33 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 1995 Jan 1 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Synthesis and characterization of 3‐aryl‐2‐(polystyryl)cyclopropenones via cyclopropenium ion substitution on polystyrene
AU - Weidner, C. H.
AU - Long, Timothy Edward
PY - 1995/1/1
Y1 - 1995/1/1
N2 - 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.
AB - 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.
KW - cyclopropenium
KW - cyclopropenone
KW - Friedel–Crafts
KW - polymeric cyclopropenone
KW - polystyrene
KW - reactive oligomer
KW - TGA
UR - http://www.scopus.com/inward/record.url?scp=0029196913&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0029196913&partnerID=8YFLogxK
U2 - 10.1002/pola.1995.080330101
DO - 10.1002/pola.1995.080330101
M3 - Article
AN - SCOPUS:0029196913
VL - 33
SP - 1
EP - 6
JO - Journal of Polymer Science, Part A: Polymer Chemistry
JF - Journal of Polymer Science, Part A: Polymer Chemistry
SN - 0887-624X
IS - 1
ER -