An exploration of supramolecular tape-like assemblies formed by pyridine dicarboxylates

Abstract

This investigation builds on a previous survey of the solid-state behaviour of pyridinedicarboxylate diesters, an overview of which is presented in Chapter 1. These compounds have been shown to form tape-like assemblies, mediated by a novel triple hydrogen bond motif.
Chapter 2 examines the behaviour of a small subset of these compounds in solution, some of which appear to form tape-like aggregates, as studied by 1H NMR spectroscopy. Variable temperature Raman spectroscopy has been used to observe the disruption of the crystal architecture as the sample is heated past its melting point, and the increased strength of the tapes formed by the 2,6-diesters compared to those of the 3,5-analogues has been quantitatively demonstrated by DSC.
The results of X-ray diffraction studies on the single crystals of a number of diesters formed with naphthalene and anthracene side-arms are described in Chapter 3. This series of compounds has allowed the effect of changing both the length of the alkyl linker and its position of attachment to the polyaromatic to be considered.
The solid-state behaviour of a number of chlorinated and methylated diesters are compared in Chapter 4. Chapter 5 examines the crystal architecture of a number of asymmetrical monoesters and the behaviour of these systems is compared to that of the analogous diesters.
Chapter 6 details the progress made towards the use of the 2,6-pyridinedicarboxylate synthon in the synthesis of functional materials. The solid-state behaviour of a number of other pyridine derivatives prepared during the course of the present study is described in Chapter 7.

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ORCID for Martin Grossel: orcid.org/0000-0001-7469-6854

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