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Double modular modification of thiolactone-containing polymers: towards polythiols and derived structures

Pieter Espeel UGent, Fabienne Goethals UGent, Milan M. Stamenović UGent, Lionel Petton UGent and Filip Du Prez UGent (2012) POLYMER CHEMISTRY. 3(4). p.1007-1015
abstract
A conceptual proof for the double modification (aminolysis and subsequent thiol-click modification) of thiolactone units, incorporated in linear polymer scaffolds, was elaborated. These polymers were prepared by either reversible addition-fragmentation chain transfer (RAFT) or nitroxide mediated radical polymerization (NMP) starting from a stable, readily available styrenic thiolactone monomer (St-TLa). Successful copolymerization of the latter with styrene (St) or methyl methacrylate (MMA) yielded linear polymers with varying thiolactone content (4-25%). Upon amine treatment, the ring-opening of the pendent thiolactones resulted in the formation of linear polythiols. Reaction conditions were optimized to avoid cross-linking via disulfide formation, thus preserving the linear nature of the polymer. Different primary amines (propylamine, benzylamine, ethanolamine and Jeffamine M-1000) were attached to the polymer backbone, while the PDIs remained low. The resulting polythiols are versatile scaffolds for further modification by various thiol-click reactions. In this respect, thiolmaleimide conjugation was used as a model reaction. NMR- and SEC-analyses revealed a near-quantitative double modification of thiolactone containing polystyrene (PS) and poly(methylmethacrylate) (PMMA) by subsequent treatment with propylamine and N-benzylmaleimide.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
BLOCK-COPOLYMER, MATERIALS SCIENCE, MERCAPTO GROUP, METHYL-METHACRYLATE, RAFT PROCESS, FUNCTIONAL POLYMERS, CLICK-CHEMISTRY, THIOL-ENE REACTIONS, FRAGMENTATION CHAIN TRANSFER, FREE-RADICAL POLYMERIZATION
journal title
POLYMER CHEMISTRY
Polym. Chem.
volume
3
issue
4
pages
1007 - 1015
Web of Science type
Article
Web of Science id
000301199600025
JCR category
POLYMER SCIENCE
JCR impact factor
5.231 (2012)
JCR rank
5/82 (2012)
JCR quartile
1 (2012)
ISSN
1759-9954
DOI
10.1039/c2py00565d
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
2093507
handle
http://hdl.handle.net/1854/LU-2093507
date created
2012-04-24 14:36:05
date last changed
2012-04-25 09:44:10
@article{2093507,
  abstract     = {A conceptual proof for the double modification (aminolysis and subsequent thiol-click modification) of thiolactone units, incorporated in linear polymer scaffolds, was elaborated. These polymers were prepared by either reversible addition-fragmentation chain transfer (RAFT) or nitroxide mediated radical polymerization (NMP) starting from a stable, readily available styrenic thiolactone monomer (St-TLa). Successful copolymerization of the latter with styrene (St) or methyl methacrylate (MMA) yielded linear polymers with varying thiolactone content (4-25\%). Upon amine treatment, the ring-opening of the pendent thiolactones resulted in the formation of linear polythiols. Reaction conditions were optimized to avoid cross-linking via disulfide formation, thus preserving the linear nature of the polymer. Different primary amines (propylamine, benzylamine, ethanolamine and Jeffamine M-1000) were attached to the polymer backbone, while the PDIs remained low. The resulting polythiols are versatile scaffolds for further modification by various thiol-click reactions. In this respect, thiolmaleimide conjugation was used as a model reaction. NMR- and SEC-analyses revealed a near-quantitative double modification of thiolactone containing polystyrene (PS) and poly(methylmethacrylate) (PMMA) by subsequent treatment with propylamine and N-benzylmaleimide.},
  author       = {Espeel, Pieter and Goethals, Fabienne and Stamenovi\'{c}, Milan M. and Petton, Lionel and Du Prez, Filip},
  issn         = {1759-9954},
  journal      = {POLYMER CHEMISTRY},
  keyword      = {BLOCK-COPOLYMER,MATERIALS SCIENCE,MERCAPTO GROUP,METHYL-METHACRYLATE,RAFT PROCESS,FUNCTIONAL POLYMERS,CLICK-CHEMISTRY,THIOL-ENE REACTIONS,FRAGMENTATION CHAIN TRANSFER,FREE-RADICAL POLYMERIZATION},
  language     = {eng},
  number       = {4},
  pages        = {1007--1015},
  title        = {Double modular modification of thiolactone-containing polymers: towards polythiols and derived structures},
  url          = {http://dx.doi.org/10.1039/c2py00565d},
  volume       = {3},
  year         = {2012},
}

Chicago
Espeel, Pieter, Fabienne Goethals, Milan M. Stamenović, Lionel Petton, and Filip Du Prez. 2012. “Double Modular Modification of Thiolactone-containing Polymers: Towards Polythiols and Derived Structures.” Polymer Chemistry 3 (4): 1007–1015.
APA
Espeel, P., Goethals, F., Stamenović, M. M., Petton, L., & Du Prez, F. (2012). Double modular modification of thiolactone-containing polymers: towards polythiols and derived structures. POLYMER CHEMISTRY, 3(4), 1007–1015.
Vancouver
1.
Espeel P, Goethals F, Stamenović MM, Petton L, Du Prez F. Double modular modification of thiolactone-containing polymers: towards polythiols and derived structures. POLYMER CHEMISTRY. 2012;3(4):1007–15.
MLA
Espeel, Pieter, Fabienne Goethals, Milan M. Stamenović, et al. “Double Modular Modification of Thiolactone-containing Polymers: Towards Polythiols and Derived Structures.” POLYMER CHEMISTRY 3.4 (2012): 1007–1015. Print.