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‘Click’ functionalization of cryogels conveniently verified and quantified using high- resolution MAS NMR spectroscopy

Wim Van Camp (UGent) , Tuğba Dışpınar (UGent) , Bart Dervaux (UGent) , Filip Du Prez (UGent) , José Martins (UGent) and Bernd Fritzinger (UGent)
(2009) MACROMOLECULAR RAPID COMMUNICATIONS. 30(15). p.1328-1333
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Abstract
Chemical modification reactions of alkyne containing polyHEMA-based macroporous network structures (cryogels) by Cu(I) catalyzed azide-alkyne 'click' cycloaddition reactions and their monitoring and quantification with high-resolution magic angle spinning (hr-MAS) NMR spectroscopy are reported. Complete conversion is obtained when benzylazide is reacted with the grafted alkyne function, but only partial conversion is observed when using azide-modified poly(ethylene glycol) (PEG-N-3). Subsequent addition of benzylazide consumes all remaining alkyne groups. All chemical modifications are easily monitored at each stage using hr-MAS NMR spectroscopy. The alkyne functionality and the resulting triazole ring provide well resolved H-1 resonances to monitor and quantify the progress of such 'click' reactions in general.
Keywords
BIOSEPARATION, POLYESTERS, cryogel, Author Keywords: 'click' chemistry, high-resolution MAS NMR spectroscopy, functionalization, macroporous networks, KeyWords Plus: POLY(2-HYDROXYETHYL METHACRYLATE), POLYMERIC CRYOGELS, MATERIALS SCIENCE, PEGYLATION, CHEMISTRY, MONOLITHS, MOLECULES, NETWORKS

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Chicago
Van Camp, Wim, Tuğba Dışpınar, Bart Dervaux, Filip Du Prez, José Martins, and Bernd Fritzinger. 2009. “‘Click’ Functionalization of Cryogels Conveniently Verified and Quantified Using High- Resolution MAS NMR Spectroscopy.” Macromolecular Rapid Communications 30 (15): 1328–1333.
APA
Van Camp, Wim, Dışpınar, T., Dervaux, B., Du Prez, F., Martins, J., & Fritzinger, B. (2009). “Click” functionalization of cryogels conveniently verified and quantified using high- resolution MAS NMR spectroscopy. MACROMOLECULAR RAPID COMMUNICATIONS, 30(15), 1328–1333.
Vancouver
1.
Van Camp W, Dışpınar T, Dervaux B, Du Prez F, Martins J, Fritzinger B. “Click” functionalization of cryogels conveniently verified and quantified using high- resolution MAS NMR spectroscopy. MACROMOLECULAR RAPID COMMUNICATIONS. D-69451 WEINHEIM, GERMANY: WILEY-V C H VERLAG GMBH; 2009;30(15):1328–33.
MLA
Van Camp, Wim, Tuğba Dışpınar, Bart Dervaux, et al. “‘Click’ Functionalization of Cryogels Conveniently Verified and Quantified Using High- Resolution MAS NMR Spectroscopy.” MACROMOLECULAR RAPID COMMUNICATIONS 30.15 (2009): 1328–1333. Print.
@article{740327,
  abstract     = {Chemical modification reactions of alkyne containing polyHEMA-based macroporous network structures (cryogels) by Cu(I) catalyzed azide-alkyne 'click' cycloaddition reactions and their monitoring and quantification with high-resolution magic angle spinning (hr-MAS) NMR spectroscopy are reported. Complete conversion is obtained when benzylazide is reacted with the grafted alkyne function, but only partial conversion is observed when using azide-modified poly(ethylene glycol) (PEG-N-3). Subsequent addition of benzylazide consumes all remaining alkyne groups. All chemical modifications are easily monitored at each stage using hr-MAS NMR spectroscopy. The alkyne functionality and the resulting triazole ring provide well resolved H-1 resonances to monitor and quantify the progress of such 'click' reactions in general.},
  author       = {Van Camp, Wim and D{\i}\c{s}p{\i}nar, Tu\u{g}ba and Dervaux, Bart and Du Prez, Filip and Martins, Jos{\'e} and Fritzinger, Bernd},
  issn         = {1022-1336},
  journal      = {MACROMOLECULAR RAPID COMMUNICATIONS},
  keyword      = {BIOSEPARATION,POLYESTERS,cryogel,Author Keywords: 'click' chemistry,high-resolution MAS NMR spectroscopy,functionalization,macroporous networks,KeyWords Plus: POLY(2-HYDROXYETHYL METHACRYLATE),POLYMERIC CRYOGELS,MATERIALS SCIENCE,PEGYLATION,CHEMISTRY,MONOLITHS,MOLECULES,NETWORKS},
  language     = {eng},
  number       = {15},
  pages        = {1328--1333},
  publisher    = {WILEY-V C H VERLAG GMBH},
  title        = {{\textquoteleft}Click{\textquoteright} functionalization of cryogels conveniently verified and quantified using high- resolution MAS NMR spectroscopy},
  url          = {http://dx.doi.org/10.1002/marc.200900087},
  volume       = {30},
  year         = {2009},
}

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