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Development and characterisation of selective ion or molecular receptors

Wall, Rachel F. (2003) Development and characterisation of selective ion or molecular receptors. PhD thesis, Dublin City University.

The research entailed the Synthesis and Charactensation of a range of Molecular Receptors The target receptor was a calix[4]arene denvative, possessing a tetrahedral ’pocket’ at the lower rim defined by four p endant ligating groups, with opposing groups differing in length To achieve this, the spacer units in th e 1,3 positions of th e calixarene must differ in length than the spacer units in th e 2,4 positions by a single methylene spacer, thus generating a selective 3 - dimensional binding site. LC-UV-MS analysis of the products of the denvatisation of p-t-butyl calix[4]arene with ethyl bromo acetate has been earned out in order to optimise the synthesis of th e 1,3 disubstituted product LC-DAD and LC-UV-MS methods have been developed to successfully identify and characterise the compounds being formed in these complex reactions Obtaining reliable routes to partially substituted calixarene denvatives is of growing interest a s they provide a template for generating complex denvatives with mixed functionality and/or greater diversity. The synthesis has led to the generation of a series of partially substituted calix[4]arene denvatives, as well as derivatives of the tetrahedrally arranged target receptor. The various receptors have been assessed for lon-complexation properties by a number of methods, pnncipally NMR spectroscopy, an d ion-selective electrode stud ies In th e electrode measurements, the receptors are dispersed in a plasticised PVC membrane, and the lon-selectivity of the device is assessed. Patterns related to the selectivity of Group I, II ions an d a diverse group of anions have been determined The 1,3-diester produces a sensor that exhibits a Nernstian Response with a number of ions, but d o e s not reproduce th e well-known selectivity of th e calix[4]arene tetra esters Functionalisation at the 2,4 position with ethyl 3-bromopropionate realises a calix[4]arene denvative with differing spatial a rran g em en ts of differing binding sites, a novel diacid, d ieste r calix[4]arene denvative (fig 1) This will provide a unique platform for building a new s e n e s of calix[4]arene receptors with tetrahedral rather than an octahedral arrangement of binding sites
Item Type:Thesis (PhD)
Date of Award:2003
Supervisor(s):Diamond, Dermot and Nolan, Kieran
Uncontrolled Keywords:Receptors; Aromatic compounds; Calixarenes
Subjects:Physical Sciences > Chemistry
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 3.0 License. View License
ID Code:18262
Deposited On:27 May 2013 13:50 by Celine Campbell . Last Modified 03 Feb 2023 16:30

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