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Copyright by Michael Findlater May 2008 Copyright By Michael Findlater May 2008 The Dissertation Committee for Michael Findlater certifies that this is the approved version of the following dissertation: Adventures in Main Group Chemistry: From Molecules to Materials Committee: ___________________________ Alan H. Cowley, Supervisor ___________________________ Richard A. Jones ___________________________ Bradley J. Holliday ___________________________ Alan Campion ___________________________ Colin Abernethy iii Adventures in Main Group Chemistry: From Molecules to Materials by Michael Findlater, B.Sc. Hons Dissertation Presented to the Faculty of the Graduate School of The University of Texas at Austin in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy The University of Texas at Austin May 2008 ii Dedicated to: My Family, with whom I credit anything and everything that can be said to be good about me Acknowledgements The first and most important person I must thank is, of course, Professor Alan H. Cowley. Boss, your boundless enthusiasm for science was both encouraging and contagious in equal measure while your knowledge and insight made me (for better or worse!) the chemist I am today. The colleagues with whom I had the pleasure and privilege to work with in my time in the Cowley group all played important roles in my development in one way or another and I would be remiss without thanking you all. In particular I would to express my everlasting gratitude to Dr Nick Hill for his instruction, help, mentoring and all round ‘great bloke-edness’. Dr. Christopher Entwistle, Dr Leonardo Apostolico and Dr Gregor Reeske (who performed the original synthesis of compound 47) were sources of constant information and I was happy to have such helpful post-doctoral researchers at my disposal. My thanks also go to my fellow graduate students: Lucille Mullins, Dr Jamie N. Jones, Dr Zheng Lu (who successfully isolated the bridged dimer, 55), Dr Jennifer Moore, Dr Dragoslav Vidovic, Kalyan Vasudevan, Clint Hoberg, Adam Powell, Lauren Gehman, Rachel Butorac and Sarah Swingle. It is unimportant to list your many qualities now, as you all know the high regard in which I hold all of our friendships. It would also be exceedingly churlish of me to ignore the very important role played in my life by Christina Gomez, she remains one of my dearest friends and someone for whom I will always hold the deepest affections. During their unrelenting friendships Kristen and Monica have been sources of laughs, drinks, food, you name it at varying times, my sincerest thanks to you both. v Finally, but perhaps most importantly I want to thank my family. Everything I know most surely about morality and obligation I owe to them, though some may say that is no praise! My mother has been and continues to be an enduring force in all that I believe in about how one should conduct oneself in relation to others and in faith. My brothers have molded the man I have become through gentle guidance and forced attention! My sister, in large part, raised me and is something of a surrogate mother – though I doubt she will thank me for saying so. To my nephews and beautiful niece, I love you all. A special place is however reserved for my Father, who left me all too soon. At no point have I ever felt his absence as keenly as I do now, he was, without a doubt the smartest person I ever met and it saddens me to think he was unable to see me achieve such academic success. vi Adventures in Main Group Chemistry: From Molecules to Materials Publication No.____________ Michael Findlater, Ph.D. The University of Texas at Austin, 2008 Supervisor: Alan H. Cowley Three synthetic methods have been explored for the preparation of several novel boron-substituted amidinates and guanidinates. The extension of heterocumulene insertion chemistries to boron-aryl, boron-metallocene and boron-transition metal moieties has also been achieved and the mechanism of such insertions is addressed via density functional theory modeling techniques. The reactivity of these complexes is also explored, mainly through halide abstraction methodologies to generate boron vii cations, which are potent Lewis Acids and may be useful in promoting organic transformations or in the polymerization of ethylene. The synthesis and characterization of the elusive monomeric low valent carbenoid boron(I), a compound with a formal lone pair located upon the boron center, has been lacking. The suitability of the guanidinate ligand system to support such a species is also discussed and a combined experimental and theoretical approach to this highly topical problem is also presented. Thirdly, the use of photovoltaics (devices which convert solar energy directly into electricity) as an alternative source of energy outwith fossil fuel technologies is a rapidly growing area of interest. Initial efforts to use a novel approach, which incorporates inorganic nanocrystals wired into a conducting polymer matrix, are also presented. Successful synthetic approaches to the gallium, aluminum and indium monomeric precursors suitable for electropolymerization were developed. These compounds proved to be effective starting points for the generation of conducting polymers with embedded III/VI (Ga2S3) nanocrystals with further studies currently underway as to their III/V (InP, GaAs) compatriots. Finally, a retrospective of projects that may best be described in terms of the moniker “Loose Ends and Future Directions” will be presented. The aim of which will be to serve as a useful guidepost for further studies in the fields and topics discussed. viii Table of Contents: ACKNOWLEDGEMENTS .........................................................................................V LIST OF FIGURES.................................................................................................. XI LIST OF SCHEMES............................................................................................... XV LIST OF TABLES..................................................................................................XVI CHAPTER 1: SYNTHETIC APPROACHES TO AMIDINATE AND GUANIDINATE COMPLEXES OF BORON ............................................................ 1 INTRODUCTION....................................................................................................... 1 RESULTS AND DISCUSSION.................................................................................. 3 Synthesis via trimethylsilyl-halide elimination ......................................................................................3 Synthesis via salt metathesis....................................................................................................................7 Synthesis via carbodiimide insertion ....................................................................................................13 Reactive Boron Species Supported by Amidinate Fragments .............................................................19 CONCLUSIONS........................................................................................................28 EXPERIMENTAL.....................................................................................................29 REFERENCES..........................................................................................................37 TABLES OF CRYSTALLOGRAPHIC DATA...........................................................44 CHAPTER 2: TOWARDS BORON(I): RATIONAL LIGAND DESIGN VIA A COMBINED THEORETICAL AND EXPERIMENTAL APPROACH ....................73 INTRODUCTION......................................................................................................73 RESULTS AND DISCUSSION.................................................................................75 CONCLUSIONS........................................................................................................85 EXPERIMENTAL SECTION ...................................................................................86 REFERENCES..........................................................................................................91 TABLES OF CRYSTALLOGRAPHIC DATA...........................................................94 CHAPTER 3: PHOTOVOLTAICS: A SEEDED GROWTH APPROACH .............126 INTRODUCTION....................................................................................................126 RESULTS AND DISCUSSION...............................................................................131 Model Complexes Synthesis and Characterization............................................................................131 ix Bithiophene Complexes Synthesis and Characterization ..................................................................136 Reactivity studies of Gallium Chloride Schiff Base Complexes........................................................139 Reactivity studies of Indium substituted Schiff Base complexes .......................................................145 CONCLUSIONS......................................................................................................148 EXPERIMENTAL SECTION .................................................................................151 REFERENCES........................................................................................................158 TABLES OF CRYSTALLOGRAPHIC DATA.........................................................161 CHAPTER 4: LOOSE ENDS AND FUTURE DIRECTIONS ................................180 TRANSITION METAL CHEMISTRY ....................................................................180
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