This thesis is concerned with the synthesis of new anion receptors and describes the anion binding and anion transport properties of these compounds Ten squaramide receptors (A) based on a steroidal cholapod backbone have been synthesised. Association constants for the squaramide receptors with chloride anions were assessed in chloroform and were found to be exceptionally high, up to 1.2 x 1014 M-1 , and in most cases were higher than that of all chloride receptors previously published by the A. P. Davis group. The introduction of electron withdrawing aromatic groups led to increased association constants, as did the introduction of an additional hydrogen bond donor at position Z. The chloride transport properties of the squaramide receptors were also studied, however rates were disappointing. Six receptors based on a trans-decalin scaffold (B) have also been synthesised. These receptors feature two thiourea binding groups and have alkyl chains of varying lengths on the aromatic rings. Association constants of the decalin receptors for chloride were measured in DMSO-d6/O.5% H20 and in chloroform, and were found to be almost identical for each receptor. The chloride transport properties of the decalin receptors were also studied and it was found that as the length of the alkyl substituent R was increased, transport rates also increased up until R = n-hexyl, after which further increasing the length of the alkyl substituent caused transport rates to decrease. Some progress has also been made towards the synthesis of a novel tricyclic receptor (C).
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:685437 |
| Date | January 2015 |
| Creators | Edwards, Sophie Jane |
| Publisher | University of Bristol |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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