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N-Heterocyclic Carbene Ligated Group 11 Trimethylsilylchalcogenolates: Building Blocks for Heterometallic Chalcogenide Molecules

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N-Heterocyclic Carbene Ligated Group 11 Trimethylsilylchalcogenolates: Building Blocks for Heterometallic Chalcogenide Molecules Western University Scholarship@Western Electronic Thesis and Dissertation Repository 4-27-2020 10:00 AM N-Heterocyclic Carbene Ligated Group 11 Trimethylsilylchalcogenolates: Building Blocks for Heterometallic Chalcogenide Molecules Dickron Richard Nahhas The University of Western Ontario Graduate Program in Chemistry A thesis submitted in partial fulfillment of the equirr ements for the degree in Master of Science © Dickron Richard Nahhas 2020 Follow this and additional works at: https://ir.lib.uwo.ca/etd Part of the Inorganic Chemistry Commons Recommended Citation Nahhas, Dickron Richard, "N-Heterocyclic Carbene Ligated Group 11 Trimethylsilylchalcogenolates: Building Blocks for Heterometallic Chalcogenide Molecules" (2020). Electronic Thesis and Dissertation Repository. 6985. https://ir.lib.uwo.ca/etd/6985 This Dissertation/Thesis is brought to you for free and open access by Scholarship@Western. It has been accepted for inclusion in Electronic Thesis and Dissertation Repository by an authorized administrator of Scholarship@Western. For more information, please contact [email protected]. Abstract The synthesis of heterometallic chalcogenide molecules requires the continued investigation into the appropriate reagents necessary to introduce metal – chalcogen bonds in a controlled fashion. – Trimethylsilyl metallochalcogenolates (MESiMe3) act as synthons introducing “ME “ in solution upon reacting with an appropriate ternary metal reagent, MX (X= halide, acetate, etc.). Recent work makes use of N–heterocyclic carbenes (NHCs) as a class of ancillary ligand that can stabilize these reagents and the heterometallic chalcogenide molecules obtained with them. Building on previous work, this thesis describes the synthesis of group 11 trimethylsilyl metallochalcogenolates stabilized by bis–1,3– tritylimidazole–2–ylidene (abbreviated ITr) to build this library of compounds and investigate their ’ reactivity towards dinuclear chalcogenide molecules, [(ITr)2M(μ2–E)M ] (M=Cu, Ag, Au; E=S, Se). Surprisingly, the reaction of [ITrMESiMe3] with [ITrMOAc] did not yield the desired products in a selective manner. Attempts are made to rationalize the failure to obtain both the homo and heterometallic compounds by this general method and by other previously established techniques. Keywords: metal chalcogenides, heterometallic, trimethylsilyl metallochalcogenolates, N-heterocyclic carbenes (NHCs) ii Summary for Lay Audience Transition metal chalcogenides are compounds made of a combination of an element from the middle of the periodic table together with one of the chalcogens (oxygen, sulfur, selenium, or tellurium). These solids are found in nature as minerals and ores from which valuable metals can be extracted; however, recent work has shown their suitability for a wide variety of applications ranging from photovoltaic absorbers to catalysts. In engineering the material properties of these compounds further, chemists have learned that controlling the chemical bonding between these elements and forming discrete molecules allows for improved control of their material properties. The challenge of assembling these molecules in a controlled manner is often overcome using other organic molecules, known as ligands, which chemically bond to the metal or chalcogen atoms to effectively control the degree of bonding between these types of elements. The nature of the chemical bond between the ligand and the metal, as well as the ability for this ligand to encompass the metal atom, controls the ability to isolate molecular metal chalcogenides. The work in this field is ongoing, with homometallic (one metal) or heterometallic (two or more metal types) molecules having been made. To continue developing the synthesis of heterometallic chalcogenide molecules, the work in this thesis describes a contribution to the growing library of metal-chalcogen complexes incorporating N-heterocyclic carbenes (NHCs) as effective ligands, and investigating the chemical reactions thought to be able to produce a new class of dinuclear, heterometallic molecules. iii Acknowledgments The last two and a half years of my life at Western have been a whirlwind of learning and growth. London, Ontario, has been good to me and provided me with a chance to grow as a person and make new connections with many people, all of whom deserve thanks for their part in helping me come this far. First, I would like to thank the University for funding my two years here and extend my deepest and most humble feelings of gratitude and appreciation to Dr. John Corrigan for his patient tutelage and mentorship. Thank you for allowing me to be part of the lab and for helping me grow as a researcher, challenging my ideas and inspiring new ones. Your patience and guidance were always felt, and I look forward to reading about the work the group produces in the future. In my time here, I have had the privilege of working with many members of the Corrigan group, past and present. Though there are many people to thank, I would like to make a special mention to Alex Polgar and Jay Kyungseeop Lee for being here at the start. Though I only had a year with Mr. Polgar, it was a memorable one filled with discussions about chemistry and life; I wish you all the success I know is already on its way to you. To Mr. Lee, who was here with me in the trenches for the entirety of my graduate studies, I owe a tremendous amount for being there to listen when reactions wouldn’t work and for encouraging me when reactions did. You are a brilliant chemist and my hope is that you acknowledge yourself as such. Thank you to Connor, Alicia, Rachel and Khayrat; every member of the Corrigan group that I encountered during my time here had to endure my long tangents about my research and theirs. While some happily reciprocated, others quietly and politely obliged me this pleasure. For this I am grateful. To the new members of the Corrigan group, I am sad our time was short but am confident you will do great things here. I look forward to hearing about the achievements of Zahra, Mansha, Johanna, Julia and Evie, as they move on from their undergraduate studies, and thank them for always being interested in learning about what we do. Having you all around in the lab and in group meetings made for a fun time and I am confident you will all succeed in your respective paths. To the new graduate students Andy and Nils, I would like to offer my sincerest appreciation and gratitude for making the end of my time here very memorable. To Andy, thank you for always being willing to entertain my questions about your project. Dr. Cluster will go on to great things, of this I am sure. To Nils, the “crazy German guy” thank you for taking the time to befriend an old man and for always being willing to talk about chemistry with the same amount of (if not more) passion as I do. Your passion for your iv research and your students is inspiring, and I hope you hold onto this passion as you work in the Corrigan lab and beyond. To my parents, family, and friends thank you for always believing in me and supporting me. To my sister Vana thank you for always being excited to hear about the lab and for taking an interest in my work. To my mom and dad, thank you for patiently listening to my concerns and offering solutions where you could. A special mention to so many of my friends from the Toronto area, those I grew up with, those I met during my undergraduate studies and those I see in passing. Each of you helped in your way to keep me level – headed during my time as a student. Last, but certainly not least, I would like to thank my partner Laura for all her love and support during my time as a Master’s student. I came to London to earn a Master’s degree and got lucky in finding a partner for life. Thank you for taking an (sometimes) earnest interest in my work in the lab. Thank you for putting up with the long nights, the early days and having me bring my work home with me. I am excited for what the future has in store for us and blessed to have you by my side. Though I can’t promise I won’t continue to bring chemistry home with me, I look forward to having our lives grow and be filled with so much more. v Table of Contents Abstract ....................................................................................................................................................... ii Summary for Lay Audience ....................................................................................................................... iii Acknowledgments ...................................................................................................................................... iv List of Schemes ........................................................................................................................................ viii List of Tables ........................................................................................................................................... viii List of Figures ............................................................................................................................................ ix List of Appendices .................................................................................................................................... xii List of Abbreviations ............................................................................................................................... xiii Chapter 1 ..................................................................................................................................................
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