Synthesis and complexation studies of new triazole bridged-calix[4]arenes and attempts to synthesize a modified Homooxacalix[4]acenaphthene

Aljabri, Mahmood (2014) Synthesis and complexation studies of new triazole bridged-calix[4]arenes and attempts to synthesize a modified Homooxacalix[4]acenaphthene. Masters thesis, Memorial University of Newfoundland.

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Abstract

The possibility of synthesizing compounds capable of selective binding to metal ions has been extensively investigated. Such investigations mainly aim at making compounds available for metal ion testing. This work has been motivated by the fact that synthesizing proper receptors that can selectively and specifically interact with metal ions of interest is important for the development of supramolecular chemistry. This thesis begins by providing a brief introduction to the main concept of supramolecular chemistry, often referred to as “Host-Guest Chemistry”. Chapter 1 also describes the forces that control supramolecular interactions between host and guest molecules. A thorough discussion about calixarenes, whose synthesis and complexation properties were one of the main objectives of this work, and the techniques used for the complexation studies are also presented in Chapter 1. In Chapter 2, the syntheses of two new molecular receptors namely bis(naphthyl)methane-bridged macrocycles are described. These two receptors were subsequently characterized by ¹H- and ¹³C-NMR spectroscopy and mass spectrometry. Chapter 2 also presents a study of the complexation properties of these receptors with different metal ions of interest which have been investigated using ¹H-NMR and fluorescence spectroscopy. Our results have shown that these two compounds are selective towards Fe³⁺, Hg²⁺ and Cu²⁺ in a mixed 4:1 acetonitrile: chloroform solvent. Chapter 3 presents the synthesis procedures that have been followed to develop fluorescent chemosensors based on acenaphthene-modified calix[4]arene-triazoles. The selectivity of these chemosensors towards metal ions has been studied using fluorescence and ¹H-NMR spectroscopy. The results obtained from these techniques which show their complexation properties are explained in detail in this chapter. In Chapter 4, attempts made towards the modification of homooxacaxalix[4]-acenaphthene are presented. This modification has been performed with the hope that such a compound could selectively bind C⁷⁰ fullerene, since the prototype compound was found to be selective towards C⁶⁰ fullerene. Synthetic work towards the modification of homooxacaxalix[4]acenaphthene is on-going.

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