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International Journal of Polymer Science
Volume 2012 (2012), Article ID 586594, 9 pages
http://dx.doi.org/10.1155/2012/586594
Research Article

A Synthetic Route to Quaternary Pyridinium Salt-Functionalized Silsesquioxanes

1Department of Chemistry, University of Tromsø, Hansine Hansens veg, 9037 Tromsø, Norway
2Chemisches Institut, Otto-von-Guericke-Universität, Universitätsplatz 2, 39106 Magdeburg, Germany

Received 5 June 2012; Accepted 12 August 2012

Academic Editor: Yoshiro Kaneko

Copyright © 2012 Nataliya Kostenko et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A synthetic route to potentially biocidal silsesquioxanes functionalized by quaternary pyridinium functionalities has been developed. N-Alkylation reactions of the precursor compounds 4-(2-(trimethoxysilyl)ethyl)-pyridine (5) and 4-(2-trichloro-silylethyl)pyridine (6) with iodomethane, n-hexylbromide, and n-hexadecylbromide cleanly afforded the corresponding N-alkylpyridinium salts (710). The synthesis of a 4-(2-ethyl)pyridine POSS derivative (2) was achieved by capping of the silsesquioxane trisilanol Cy7Si7O9(OH)3 (1) via two different preparative routes. Attempts to use compound 2 as precursor for quaternary pyridinium salt-functionalized POSS derivatives were met with only partial success. Only the reaction with iodomethane cleanly afforded the new N-methylpyridinium salt 12 in high yield, whereas n-hexylbromide and n-hexadecylbromide failed to react with 2 even under forcing conditions.