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Thesis of Metallole Monomers UNIVERSITY OF CALIFORNIA, SAN DIEGO Photoluminescent Metalloles for Chemical Sensing of Nitroaromatic Explosives and Chromium(VI) A dissertation submitted in partial satisfaction of the requirements for the degree Doctor of Philosophy in Chemistry by Sarah Josepha Toal Committee in charge: Professor William C. Trogler, Chair Professor Douglas Magde Professor Karsten Meyer Professor Michael J. Sailor Professor Jan B. Talbot 2005 Copyright© Sarah Josepha Toal, 2005 All rights reserved DEDICATION For my dad, for encouraging me to study philosophy, for showing me that the quest for wisdom must never end, and that we seek knowledge, not for its own sake, but for the power to do good; For my mom, for teaching me that happiness is gained by serving others; For my brothers, Ray and Adam, who always protected me as their little sister; For my sister Mary, like whom I have always strived to be; For Noëlle, Michael, and Joy, for bringing my siblings happiness, and whom I love as my own siblings. iv TABLE OF CONTENTS Signature Page..............................................................................................................iii Dedication.....................................................................................................................iv Table of Contents...........................................................................................................v List of Symbols and Abbreviations ...............................................................................x List of Figures.............................................................................................................xiii List of Schemes...........................................................................................................xvi List of Tables.............................................................................................................xvii Acknowledgements..................................................................................................xviii Vita...............................................................................................................................xx Abstract......................................................................................................................xxii Chapter 1 Review of Metallole Chemistry, Explosives Detection, and Chromium(VI) Detection............................................................................................1 1.1 Review of Metallacyclopentadienes (Metalloles)................................................1 1.1.1 Electronic Properties of Metalloles................................................................1 1.1.2 Synthesis of Metallole Monomers.................................................................5 1.1.3 Polymetalloles and Metallole-Containing Polymers.....................................6 1.1.3.1 Poly(2,5-metalloles) and Copolymers.....................................................6 1.1.3.2 Poly(1,1-metalloles) and Copolymers.....................................................7 1.2 Review of Explosives Sensing Using Redox Polymers.....................................11 1.2.1 The Explosives Threat.................................................................................11 v 1.2.2 Fluorescent Organic Polymers for Redox Sensing of Explosives...............14 1.2.2.1 Polyacetylenes........................................................................................15 1.2.2.2 Poly(p-phenylenevinylenes)..................................................................16 1.2.2.3 Poly(p-phenyleneethynylenes)...............................................................19 1.2.2.4 Polymeric Porphyrins.............................................................................22 1.2.3 Fluorescent Inorganic Polymers for Redox Sensing of Explosives.............23 1.2.3.1 Fluoroalkylated Polysilanes...................................................................24 1.2.3.2 Polymetalloles and Metallole-Silane Copolymers.................................27 1.2.4 Resistive Sensing of Explosives Using Organic Polymers..........................29 1.2.5 Polymeric Coatings on SAW Device Sensors.............................................29 1.2.6 Inorganic Nanoparticle Sensors...................................................................33 1.2.7 Porous Silicon for Vapor-Phase Detection of Explosives...........................34 1.2.8 Colorimetric Sensors for Solid-State Explosives Detection........................35 1.3 Introduction to Chromium(VI) Toxicity and Detection.....................................36 1.3.1 Chromium Toxicity......................................................................................36 1.3.2 Industrial Uses of Chromium.......................................................................37 1.3.3 Chromium in the Environment....................................................................39 1.3.4 Methods of Chromium(VI) Detection.........................................................40 1.4 Objectives of the Dissertation............................................................................42 1.5 Acknowledgements............................................................................................43 1.6 References..........................................................................................................44 vi Chapter 2 Syntheses of Oligometalloles by Catalytic Dehydrocoupling....................51 2.1 Abstract..............................................................................................................51 2.2 Introduction........................................................................................................52 2.3 Results and Discussion......................................................................................54 2.3.1 Catalytic Dehydrocoupling Syntheses.........................................................54 2.3.2 Molecular Weights.......................................................................................58 2.3.3 Molecular Structure as Driving Force for Dehydrocoupling.......................59 2.3.4. Fluorescence of Silole Monomers, Dimers, and Polymers.........................65 2.3.5 Fluorescence Quantum Yields.....................................................................67 2.3.6 Polysilole Compared to Polygermole..........................................................69 2.4 Experimental......................................................................................................71 2.4.1 General Synthetic Techniques.....................................................................71 2.4.2 X-ray Crystal Structure Determinations......................................................71 2.4.3 Synthesis of Dihydrosilole...........................................................................72 2.4.4 Synthesis of Dihydrogermole......................................................................73 2.4.5 Synthesis of Oligo(tetraphenylsilole)..........................................................73 2.4.6 Synthesis of Oligo(tetraphenylgermole)......................................................74 2.4.7 Synthesis of Dihydrosilole Dimer................................................................74 2.4.8 Synthesis of Methylsilole Dimer.................................................................75 2.4.9 Syntheses of Dideuterosilole and Dideuterogermole...................................75 2.5 Acknowledgements............................................................................................76 2.6 References..........................................................................................................76 vii 2.7 Appendix............................................................................................................79 2.7.1 Crystal Data for Dihydrosilole.....................................................................79 2.7.2 Crystal Data for Dihydrogermole................................................................80 2.7.3 Crystal Data for Dihydrosilole Dimer..........................................................81 2.7.4 Crystal Data for Methylsilole Dimer...........................................................82 Chapter 3 Visual Detection of Trace Nitroaromatic Explosive Residue Using Photoluminescent Metallole-Containing Polymers........................................83 3.1 Abstract..............................................................................................................83 3.2 Introduction........................................................................................................83 3.3 Explosives Detection Technique........................................................................85 3.4 Results and Discussion......................................................................................88 3.5 Experimental......................................................................................................95 3.6 Acknowledgements............................................................................................95 3.7 References..........................................................................................................95 Chapter 4 Luminescent Oligo(tetraphenyl)silole Nanoparticles as Chemical Sensors for Aqueous TNT........................................................................................98 4.1 Abstract..............................................................................................................98 4.2
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