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Synthesis of dimeric pyridylguanidinium based supramolecular structures stable in polar and aqueous solvent systems

Synthesis of dimeric pyridylguanidinium based supramolecular structures stable in polar and aqueous solvent systems
Synthesis of dimeric pyridylguanidinium based supramolecular structures stable in polar and aqueous solvent systems
This thesis describes the synthesis of a series of pyridyl guanidinium-carboxylates. Dilution and spectroscopic studies are made thus affording information concerning the molecular forces controlling their dimerisation. Chapter I provides an introduction to the thesis and discusses, in the main part, the thermodynamics of self-assembly with particular focus given to guanidinium-carboxylates. Chapter II describes the syntheses and dimerisation studies undertaken and Chapter III contains the experimental procedures and results. The dimerisation of the pyridylguanidinium-carboxylates was investigated in DMSO and H2O/DMSO mixtures using isothermal calorimetric and NMR dilution techniques and the relative importance of H-bonding, ?- ? stacking, electrostatic and hydrophobic interactions in constructing a dimeric self-assembled system in polar and aqueous environment has been investigated.While most of the guanidinium-carboxylates show excellent dimerisation in DMSO (~ Kdim = 7692±1124 M-1) and 10% H2O/DMSO (~ Kdim= 2695±151 M-1), some of them exhibit entropy driven dimerisation in an aqueous environment containing up to 50% (~Kdim= 55±8 M-1) and 75% (~Kdim= 27±7 M-1) H2O in DMSO.
Tesfatsion, Biniam Fessehaye
8d50ed1d-fed7-4a31-ba63-ba9c900e9f22
Tesfatsion, Biniam Fessehaye
8d50ed1d-fed7-4a31-ba63-ba9c900e9f22
Bloodworth, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c

Tesfatsion, Biniam Fessehaye (2011) Synthesis of dimeric pyridylguanidinium based supramolecular structures stable in polar and aqueous solvent systems. University of Southampton, School of Chemistry, Doctoral Thesis, 249pp.

Record type: Thesis (Doctoral)

Abstract

This thesis describes the synthesis of a series of pyridyl guanidinium-carboxylates. Dilution and spectroscopic studies are made thus affording information concerning the molecular forces controlling their dimerisation. Chapter I provides an introduction to the thesis and discusses, in the main part, the thermodynamics of self-assembly with particular focus given to guanidinium-carboxylates. Chapter II describes the syntheses and dimerisation studies undertaken and Chapter III contains the experimental procedures and results. The dimerisation of the pyridylguanidinium-carboxylates was investigated in DMSO and H2O/DMSO mixtures using isothermal calorimetric and NMR dilution techniques and the relative importance of H-bonding, ?- ? stacking, electrostatic and hydrophobic interactions in constructing a dimeric self-assembled system in polar and aqueous environment has been investigated.While most of the guanidinium-carboxylates show excellent dimerisation in DMSO (~ Kdim = 7692±1124 M-1) and 10% H2O/DMSO (~ Kdim= 2695±151 M-1), some of them exhibit entropy driven dimerisation in an aqueous environment containing up to 50% (~Kdim= 55±8 M-1) and 75% (~Kdim= 27±7 M-1) H2O in DMSO.

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Published date: December 2011
Organisations: University of Southampton, Chemistry

Identifiers

Local EPrints ID: 341813
URI: http://eprints.soton.ac.uk/id/eprint/341813
PURE UUID: 17f60016-c736-4643-a985-007da400e515
ORCID for Sally Bloodworth: ORCID iD orcid.org/0000-0003-2219-3635

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Date deposited: 12 Nov 2012 14:45
Last modified: 06 Jun 2018 12:49

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Contributors

Author: Biniam Fessehaye Tesfatsion
Thesis advisor: Sally Bloodworth ORCID iD

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