Synthesis and Crystal Structure of Multifunctional Tosylate as Basis for Star-shaped Poly(2-ethyl-2-oxazoline)s
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Hoogenboom, Richard; Fijten, Martin W. M.; Kickelbick, Guido; Schubert, Ulrich S.
- 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.
- Year:
- 2010
- Type of Publication:
- Article
- Journal:
- Beilstein Journal of Organic Chemistry
- Volume:
- 6
- Pages:
- 771 - 783