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Hegewald, J. ; Pionteck, J. ; Häußler, L. ; Komber, H. ; Voit, B.
End-functionalized polystyrene by ATRP: a facile approach to primary amino and carboxylic acid terminal groups

Monoamino-terminated and monocarboxylic acid-terminated polystyrenes containing active halogenated end groups were prepared by atom transfer radical polymerization (ATRP) using the so-called initiator method and protective group chemistry. -Chloropropionates were synthesized and utilized as initiators containing the tert-butoxycarbonyl (t-BOC)-protected amino and the tert-butyl (t-Bu)-protected carboxylic acid function, respectively. Optimum polymerization conditions were attained using CuCl/N,N,N,N,N-pentamethyldiethylenetriamine (PMDETA) as catalyst and 10 vol % n-butanol as homogenizing agent at 110 °C. However, targeting larger quantities an alternative route was established employing 50 vol % N,N-dimethylformamide (DMF). Subsequent hydrolysis of the -tert-butoxycarbonyl polystyrenes afforded well-defined polymers with quantitative deprotection of the functional groups. Comparatively, thermolytic cleavage of the protective sites was studied. 1H NMR verified the quantitative removal of the t-BOC-protecting groups. Furthermore, the resulting -amino--chloro polystyrenes were reacted with Sanger reagent to confirm the existence of the thereby converted primary amino groups. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3845-3859, 2009

Source
Journal of Polymer Science: Part A: Polymer Chemistry 47

Pages
3845-3859

DOI
http://dx.doi.org/10.1002/pola.23451

Published
June 2009
 
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