MALDI-TOF MS characterization of carboxyl-end-capped polystyrenes synthesized using anionic polymerization

Haining Ji, William K. Nonidez, Rigoberto C. Advincula, Grant D. Smith, S. Michael Kilbey, Mark D. Dadmun, Jimmy W. Mays

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Abstract

A comparative study of three strategies used to synthesize well-defined carboxyl-end-capped polystyrenes is reported. Structural characterization was carried out using a combination of thin-layer chromatography (TLC) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). For the reaction of polystyryl anions with 4-bromo-1,1,1- trimethoxybutane, in addition to the major product, Bu-PS-CH 2CH 2CH 2COOH, four byproducts were observed. Their mass values suggest the following structures: Bu-PS-H, Bu-PS-CH 3, Bu-PS-CH 2CH=CH-CHO, and Bu-PS-CH 2CH 2CH 2-CO-PS-Bu. The reaction of polystyryl anions with succinic anhydride generated the targeted compound, Bu-PS-CO-CH 2CH 2COOH, but also yielded the byproducts Bu-PS-H and dimer Bu-PS-CO-CH 2CH 2-CO-PS-Bu. Under appropriate conditions, the reaction of carbon dioxide gas with polystyryl anions could yield quantitative carboxyl chain-end-functionalization.

Original languageEnglish
Pages (from-to)9950-9956
Number of pages7
JournalMacromolecules
Volume38
Issue number24
DOIs
Publication statusPublished - 2005 Nov 29
Externally publishedYes

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ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Ji, H., Nonidez, W. K., Advincula, R. C., Smith, G. D., Kilbey, S. M., Dadmun, M. D., & Mays, J. W. (2005). MALDI-TOF MS characterization of carboxyl-end-capped polystyrenes synthesized using anionic polymerization. Macromolecules, 38(24), 9950-9956. https://doi.org/10.1021/ma050816q