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Publications in Scientific Journals:

R. Hoogenboom, M. Fijten, G. Kickelbick, U. Schubert:
"Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)";
Beilstein Journal of Organic Chemistry, 6 (2010), 773 - 783.



English abstract:
The synthesis of well-defined polymer architectures is of major importance for the development of complex functional materials. In this contribution, we discuss the synthesis of a range of multifunctional star-shaped tosylates as potential initiators for the living cationic ring-opening polymerization (CROP) of 2-oxazolines resulting in star-shaped polymers. The synthesis of the tosylates was performed by esterification of the corresponding alcohols with tosyl chloride. Recrystallization of these tosylate compounds afforded single crystals, and the X-ray crystal structures of di-, tetra- and hexa-tosylates are reported. The use of tetra- and hexatosylates, based on (di)pentaerythritol as initiators for the CROP of 2-ethyl-2-oxazoline, resulted in very slow initiation and illdefined polymers, which is most likely caused by steric hindrance in these initiators. As a consequence, a porphyrin-cored tetratosylate initiator was prepared, which yielded a well-defined star-shaped poly(2-ethyl-2-oxazoline) by CROP as demonstrated by SEC with RI, UV and diode-array detectors, as well as by 1H NMR spectroscopy.

Keywords:
cationic polymerization; crystal structure; living polymerization; star-polymer; tosylate


"Official" electronic version of the publication (accessed through its Digital Object Identifier - DOI)
http://dx.doi.org/10.3762/bjoc.6.96


Created from the Publication Database of the Vienna University of Technology.