Aproaches to novel molecular delivery systems

Parker, Robert Alan (1999) Aproaches to novel molecular delivery systems. University of Southampton, Doctoral Thesis.

Abstract

This thesis concerns the application of N,N’-bisbenzyl-pyridine-2,6-dicarboxamide derivatives as potential ‘supramolecular’ delivery systems for aromatic molecules, which can be attached to dendritic surfaces.

The first section provides an overview of the supramolecular chemistry and its application to molecular complexation and recognition.  The design of molecular pincers capable of complexing azo dyes and their analogues is then discussed and a possible practical system based on a ‘pre-organising’ pyridine-2,6-dicarboxamide core is investigated.

The main body of the thesis concerns the study of the behaviour of N-arylmethylamido derivatives of this system.  A number of novel N,N’-bisbenzyl-pyridine-2,6-dicarboxamides have been prepared and characterised.  Of particular interest has been their solid-state behaviour, with X-ray structural studies demonstrating the propensity of these systems to form supramolecular assemblies.  Computer molecular modelling studies have allowed an analysis of the dominant solid-state supramolecular interactions and have shown that similar behaviour might be expected in the solution and gas phases, although these systems are very conformationally mobile.

Uv spectroscopic studies have been utilised to assess the molecular complexation properties of these novel molecular pincers and provide evidence for the complex formation with a variety of guests.  The results of these studies suggest that the electronic character of host and guest play a major role in complex formation.

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