The synthesis and polymerisation of some conjugatively extended p-Xylylenes

Abstract

This thesis describes studies directed towards the preparation of new conjugatively extended p-xylylenes through in situ 1,6- or 1,8-Hoffmann elimination reactions of trimethylammonium salts. The polymers arising from these highly reactive compounds were analysed in order to determine whether or not the extra conjugation had been involved in the polymerisation process. A number of fascinating by-products were also isolated which were useful in determining the structural unit orientation in the related polymer chains. Chapter 1 highlights the areas of p-xylylene chemistry of relevance to the general theme of this thesis. Chapter 2 describes the in situ synthesis and consequent polymerisation of vinyl-extended p-xylylene from two different trimethylammonium salts. An in-depth analysis of the polymers and the two cyclic dimers produced is also included. Chapter 3 describes the in situ synthesis and polymerisation of phenyl-extended p-xylylene from two different trimethylammonium salts. Once again, an analysis of die polymer structures and the identification of the two cyclic trimers is also included. Chapter 4 describes attempts to extend the polymerisation reactions of Chapters' 2 and 3 to produce water-soluble precursor polymers from bis-sulphonium salts. Chapter 5 describes attempts to synthesise novel polymeric materials from fluorinated monomers. Chapter 6 gives experimental details for Chapters 2-5.