Anion recognition, assembly and transport properties of amidopyrrole derivatives

Abstract

This thesis describes the synthesis and study of the anion recognition, assembly and transport properties of new functionalised amidopyrrole compounds.  In the first topic, the series of simple amidopyrrole cleft receptors containing amine, ammonium and amide was the functional groups at their pendent arms has been synthesised.  These receptors have been investigated their simple anion coordination properties.  It has been found the amine functionalised amidopyrrole has had a high recognition with protonated oxo-anions as hydrogensulfate and dihydrogenphosphate even in high polar solutions like DMSO/water; however, the rest of receptors in this series have not shown any high selective anion binding.

Secondly, synthesises of new prodigiosin mimics consisting with imidazolium amidopyrrole and their analogues have been achieved in order to investigate their HCl transport across the membranes abilities.  One of them has been improved its chloride binding when has been protonated in the solution.  The solid-state studies support the compounds in protonated forms could form the chloride complexes.  Chloride and proton transport studies results also confirm that imidazolium amidopyrrole derives could used as the HCl symporters.

In the next topic, the library of amidopyrrole derives ‘tweezer’ receptors proposed to selectively bind with carboxylate anion, red dye-spacer-L-Leu-L-Asn-L-Phe, which represents to C-termini of HIV-1 protease has been prepared.  The sequencing of the highly carboxylate bound receptors have been identified from screening experiments and Edman sequencing analysis.

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