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The Electrochemistry and Fluorescence Studies of 2,3-Diphenyl Indole Derivatives

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The Electrochemistry and Fluorescence Studies of 2,3-Diphenyl Indole Derivatives THE ELECTROCHEMISTRY AND FLUORESCENCE STUDIES OF 2,3-DIPHENYL INDOLE DERIVATIVES A thesis in fulfillment of the requirements for the degree of Master of Philosophy By Nidup Phuntsho Supervisors Prof. Naresh Kumar (UNSW) A/Prof. Steve Colbran (UNSW) Prof. David StC Black (UNSW) School of Chemistry Faculty of Science University of New South Wales Kensington, Australia August 2014 PLEASE TYPE THE UNIVERSITY OF NEW SOUTH WALES Thesis/Dissertation Sheet Surname or Fam1ly name· Phuntsho First name: N1dup Other name/s: Abbreviation for degree as g1ven in the University calendar: MSc School Chemistry Faculty; Science Title· The electrochemistry and fluorescence studies of 2,3- diphenyl indole derivatives Abstract 350 words maximum: (PLEASE TYPE) A series of 2,3-diphenyl-4,6-dimethoxyindole derivatives with C-7 substitutions were successfully synthesized. All the novel indolyl derivatives were fully characterized using 1H NMR, 13C NMR, IR spectroscopy and high-resolution mass spectrometry (HRMS) techniques. Electrochemical oxidation pathways for indolyl derivatives were explored using cyclic voltammetry (CV), spectroelectrochemistry and electronic paramagnetic resonance (EPR) spectroscopy. The electrochemical mechanisms of 2,3-disubstituted-4,6- dimethoxyindole derivatives were proposed based on results obtained from the above-mentioned techniques. This thesis also includes the synthesis of novel indolyl ligands and explores their use in metal-binding fluorescence studies. Novel indolyl chemosensors based di-2-picolylamine (DPA) and a range of amino acids were synthesized. A group of biologically relevant metal ions was selected to study their bindin!1 modes and how that affected the fluorescence emission intensity of the ligands. DPA-based indole ligand was found to be Cu • ion selective. The binding mode of the metal and the ligand was most likely 1:1. • Declaration relating to disposition of project thesis/dissertation I hereby grant to the University of New South Wales or its agents the right to archive and to make available my thesis or dissertation in whole or in part in the University libraries in all forms of media, now or here after known, subject to the provisions of the Copyright Act 1968. I retain all property rights, such as patent rights. I also retain the right to use in future works (such as articles or books) all or part of this thesis or dissertation. I also authorise University Microfilms to use the 350 word abstract of my thesis in Dissertati a'cts International (this is applicable to doctoral theses only). The Un1vers1ty recogmses that there may be exceptional circumstances requ restrictions on copying or conditions on use. Requests for restriction for a period of up to 2 years must be made in writing. Requests for a longer period of restriction may be considered in exceptional circumstances and re Ulre the a roval of the Dean of Graduate Research. FOR OFFICE USE ONLY Date of completion of reqUirements for Award: THIS SHEET IS TO BE GLUED TO THE INSIDE FRC. r- T COVER OF THE THESIS ORIGINALITY STATEMENT 'I hereby declare that this submission is my own work and to the best of my knowledge it contains no materials previously published or written by another person, or substantial .. proportions of material which have been accepted for the award of any other degree of diploma at UNSW or any other educational institution, except where due acknowledgement is made in - . the thesis. Any contribution made to the research by others, with whom I l)ave worked at UNSW or elsewhere, is explicitly ackn9wledged in the thesis. I also declare that the intellectual content of this thesis is the product of my own work, except to the extent of assistance from other in the project's design and conception or in style, presentation and linguistic expression is acknowledged. ' 5 Date ...... ...~.... l .................1"7/Jo ..1~... .. .............. COPYRIGHT STATEMENT 'I hereby grant the University of New South Wales or its agents the right to archive and to make available my thesis or dissertation in whole or part in the University libraries in all forms of media, now or here after known, subject to the provisions of the Copyright Act 1968. I retain all proprietary rights, such as patent rights. I also retain the right to use in future works (such as articles or books) all or part of this thesis or dissertation. I also authorise University Microfilms to use the 350 word abstract of my thesis in Dissertation Abstract International (this is applicable to doctoral theses only). I have either used no substantial portions of copyright material in my thesis or I have obtained permission to use copyright material; where permission has not been granted I have applied/will apply for a partial restriction of the digital copy of my thesis or dissertation.' I Signed ••••• . ' ...................................... Date .. .1. b. .. .a... .. ~- .l. -~ .. .. .. .. ............................ AUTHENTICITY STATEMENT 'I certify that the Library deposit digital copy is a direct equivalent of the final officially approved version of my thesis. No emendation of content has occurred and if there are any minor variations in formatting, they are the result of the conversion to dig at.' Signed Date ...... l~ .. ~ ... ~.. ~ ............................................ .. Originality Statement ‘I hereby declare that this submission is my own work and to the best of my knowledge it contains no materials previously published or written by another person, or substantial proportions of material which have been accepted for the award of any other degree of diploma at UNSW or any other educational institution, except where due acknowledgement is made in the thesis. Any contribution made to the research by others, with whom I have worked at UNSW or elsewhere, is explicitly acknowledged in the thesis. I also declare that the intellectual content of this thesis is the product of my own work, except to the extent of assistance from other in the project’s design and conception or in style, presentation and linguistic expression is acknowledged.’ Signed………………………………………… … Date……………………………………………… i Abstract A series of 2,3-diphenyl-4,6-dimethoxyindole derivatives with C-7 substitutions were successfully synthesized. All the novel indolyl derivatives were fully characterized using 1H NMR, 13C NMR, IR spectroscopy and high resolution mass spectrometry (HRMS) techniques. Electrochemical oxidation pathways for indolyl derivatives were explored using cyclic voltammetry (CV), spectroelectrochemistry and electronic paramagnetic resonance (EPR) spectroscopy. The electrochemical mechanisms of 2,3-disubstituted- 4,6-dimethoxyindole derivatives were proposed based on results obtained from the above-mentioned techniques. This thesis also includes the synthesis and use of novel indolyl ligands in metal-binding fluorescence studies. Novel indolyl chemosensors based on di-2- picolylamine (DPA) and a range of amino acids were synthesized. The chemosensors were investigated for their fluorescence response and binding modes to a group of biologically relevant metal ions. The DPA-based indole ligand was found to be Cu2+ selective, and the binding mode of the metal to the ligand was predicted to be 1:1. ii Acknowledgements I would like to express my gratitude to my supervisors Prof. Naresh Kumar and A/Prof Steve Colbran for giving me the opportunity to do my Master’s degree under their supervision. I also thank them for all their assistance, support and encouragement throughout the course of the project. I wish to thank all the staff of the School of Chemistry at UNSW for all the help they have given me. Special thanks goes to Dr. Jim Hook and Dr. Doug Lawes for the NMR spectroscopy support. Many thanks to the past and present members of the Kumar and Black group especially Adeline for her time reading and correcting my thesis. Thanks to Thanh, Kitty, Samuel, Ray, Ren, Murat, Ibrahim, Hakan, Dr George Iskander and Dr Abel Salek for their support. Also, I would like to give many thanks to the Colbran group for their help and advice. I would also like to thank Australian Government (AusAID) for funding me to pursue this Master’s degree, and all the Australian people for being very kind and friendly. Finally, I would like to thank my family for their love and support throughout this journey. iii Table of Contents Originality Statement .................................................................................................... i Abstract ......................................................................................................................... ii Acknowledgements ...................................................................................................... iii Table of Contents ......................................................................................................... iv Abbreviations………………………………………………………………………..vii CHAPTER 1: Introduction .......................................................................................... 1 1.1. General background to indoles ........................................................................... 1 1.2. General methods of indole ring synthesis .......................................................... 2 1.3. Indole chemistry ................................................................................................. 4 1.3.1. General reactions ......................................................................................... 4 1.3.2 Radical chemistry of indoles .......................................................................
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