Modular design of glyco-microspheres via mild pericyclic reactions and their quantitative analysis

Kaupp, Michael, Vogt, Andrew P., Natterodt, Jens C., Trouillet, Vanessa, Gruendling, Till, Hofe, Thorsten, Barner, Leonie, & Barner-Kowollik, Christopher (2012) Modular design of glyco-microspheres via mild pericyclic reactions and their quantitative analysis. Polymer Chemistry, 3(9), pp. 2605-2614.

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The facile and efficient functionalization of porous poly(glycidyl methacrylate) (pGMA) microspheres via hetero Diels-Alder (HDA) chemistry with poly(3-O-acryloyl-1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranoside) (pAIpGlc) prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization employing electron deficient thiocarbonylthio compounds (benzyl pyridin-2-yldithioformate (BPDF)) is described in detail. The efficiency of the employed ‘grafting to' approach is qualitatively and quantitatively analyzed. Initially the microspheres are functionalized with a highly reactive diene - cyclopentadiene (Cp) - in one step with sodium cyclopentadienide, and subsequently reacted with a protected glycopolymer (number-average molecular weight, M-n = 4200 g mol(-1); polydispersity index, PDI = 1.2) that carries a thiocarbonyl moiety functioning as a dienophile. The functionalization of the microspheres is achieved under mild conditions (T = 50 degrees C) with trifluoroacetic acid (TFA) as a readily removable catalyst. Deprotection of the grafted pAIpGlc to poly(3-O-acryloyl-alpha,beta-D-glucopyranoside) (pAGlc) can be performed after functionalization in one pot with formic acid at ambient temperature. The obtained loading capacity is 2.63 x 10(19) chains per g and the grafting density is close to 0.16 chains per nm(2). Quantitative analysis of the grafting densities is achieved via elemental analysis; the pore size distribution before functionalization was analyzed by inverse size exclusion chromatography (iSEC). Further employed characterization techniques include scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS) and high resolution attenuated total reflectance (ATR) FT-IR microscopy supporting the successful modification of the microspheres.

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ID Code: 97480
Item Type: Journal Article
Refereed: Yes
DOI: 10.1039/c2py20369c
ISSN: 1759-9954
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 28 Jul 2016 01:45
Last Modified: 03 Aug 2016 03:11

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