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Atropisomeric recognition molecules: Receptors, switches and polymers.
The synthesis, characterization and utility of atropisomer molecules, bearing a restricted rotation, has been investigated. The core of the systems developed consists of a naphthalene tetracarboxyldiimide with restricted rotation existing about the Caryl-Nimide bond. The focal atropisomer, naphthalene diacid was fully characterized by 1 H and 13C NMR, HRMS and X-ray crystallography. The ability of this molecule to act as a molecular recognition receptor was demonstrated through a series of binding and screening experiments. In addition, the naphthalene diacid platform displayed the ability to perform as a molecular switch. A single sample of the diacid was cycled through an 'on-off' series multiple times with excellent reproducibility and repeatability. Finally, the derivitization of naphthalene diacid was carried out with a selection of amines, all of which were characterized. In particular, the 2-aminopyridine derivative was investigated for its ability to act as a molecular receptor for diacid guest molecules.; The incorporation of molecules with a restricted rotation into cross-linked polymer matrices was demonstrated. The focus was on the synthesis and optimization of the polymer precursors and random co-polymers. It was found that incompatibility issues based on different rates of reaction of the monomers prevents the formation of a random co-polymer. To address this issue, a new cross-linker was synthesized, that was compatible with and whose rate of reaction matched that of the cross linker.