Investigations into the synthesis of upper-rim functionalised calix[4]arenes and their applications

Gardiner, William (2016) Investigations into the synthesis of upper-rim functionalised calix[4]arenes and their applications. Doctoral thesis, University of East Anglia.

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In this thesis, the development of three efficient protocols for the generation of upper-rim ABBB, ABAC and ABCD functionalised calix[4]arenes, in addition to a number of novel AAAAAB functionalised calix[6]arenes is described. For the generation of the ABAC type systems, an ionic hydrogenation between the known 1,3-diformyl calix[4]arene and para-iodophenyl urea under optimised reaction conditions to favour desymmetrisation though mono-substitution. To generate ABBB type systems, a protocol previously established within the Bew group that exploits the mono-selective Mannich reaction of calix[4]arene, aqueous dimethylamine and formalin is developed. Whilst for the ABCD type systems, previous studies in the Bew group are built upon to show how a mechanochemical, intramolecular, Cannizzaro reaction can function as a highly efficient means of desymmetrising the upper-rim of 1,3-diformyl functionalised calix[4]arenes. It is subsequently demonstrated how this ‘suite’ of protocols can be applied to the construction of fluorogenic sensors (Chapter 2), redox-active and 1,2,3-triazole linked cavitands (Chapter 3) and non-linear optical materials (Chapter 4); advanced materials which would have been difficult to access efficiently using other means.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Jackie Webb
Date Deposited: 06 Feb 2017 14:53
Last Modified: 06 Feb 2017 14:53


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