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Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s

Richard Hoogenboom UGent, Martin WM Fijten, Guido Kickelbick and Ulrich S Schubert (2010) BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 6. p.773-783
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 hexa-tosylates, based on (di)pentaerythritol as initiators for the CROP of 2-ethyl-2-oxazoline, resulted in very slow initiation and ill-defined polymers, which is most likely caused by steric hindrance in these initiators. As a consequence, a porphyrin-cored tetra-tosylate 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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
living polymerization, star-polymer, crystal structure, cationic polymerization, tosylate, POLYMERIZATION, POLYMERS, POLYOXAZOLINES, 2-ETHYL-2-OXAZOLINE, POLY(2-OXAZOLINE)S, 2-OXAZOLINES, OXAZOLINES, BIPYRIDINE, PORPHYRIN
journal title
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Beilstein J. Org. Chem.
volume
6
issue title
Functionalized polymers : synthesis and properties
pages
773 - 783
Web of Science type
Article
Web of Science id
000281699000001
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
1.515 (2010)
JCR rank
30/56 (2010)
JCR quartile
3 (2010)
ISSN
1860-5397
DOI
10.3762/bjoc.6.96
language
English
UGent publication?
yes
classification
A1
copyright statement
I have retained and own the full copyright for this publication
id
1047149
handle
http://hdl.handle.net/1854/LU-1047149
date created
2010-09-29 13:33:46
date last changed
2017-05-05 12:33:50
@article{1047149,
  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 hexa-tosylates, based on (di)pentaerythritol as initiators for the CROP of 2-ethyl-2-oxazoline, resulted in very slow initiation and ill-defined polymers, which is most likely caused by steric hindrance in these initiators. As a consequence, a porphyrin-cored tetra-tosylate 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.},
  author       = {Hoogenboom, Richard and Fijten, Martin WM and Kickelbick, Guido and Schubert, Ulrich S},
  issn         = {1860-5397},
  journal      = {BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {living polymerization,star-polymer,crystal structure,cationic polymerization,tosylate,POLYMERIZATION,POLYMERS,POLYOXAZOLINES,2-ETHYL-2-OXAZOLINE,POLY(2-OXAZOLINE)S,2-OXAZOLINES,OXAZOLINES,BIPYRIDINE,PORPHYRIN},
  language     = {eng},
  pages        = {773--783},
  title        = {Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s},
  url          = {http://dx.doi.org/10.3762/bjoc.6.96},
  volume       = {6},
  year         = {2010},
}

Chicago
Hoogenboom, Richard, Martin WM Fijten, Guido Kickelbick, and Ulrich S Schubert. 2010. “Synthesis and Crystal Structures of Multifunctional Tosylates as Basis for Star-shaped Poly(2-ethyl-2-oxazoline)s.” Beilstein Journal of Organic Chemistry 6: 773–783.
APA
Hoogenboom, R., Fijten, M. W., Kickelbick, G., & Schubert, U. S. (2010). Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 6, 773–783.
Vancouver
1.
Hoogenboom R, Fijten MW, Kickelbick G, Schubert US. Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2010;6:773–83.
MLA
Hoogenboom, Richard, Martin WM Fijten, Guido Kickelbick, et al. “Synthesis and Crystal Structures of Multifunctional Tosylates as Basis for Star-shaped Poly(2-ethyl-2-oxazoline)s.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 6 (2010): 773–783. Print.