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Synthesis, Reactivity, Structural and Spectral Properties. James Bryan Carroll University of Missouri-St University of Missouri, St. Louis IRL @ UMSL Dissertations UMSL Graduate Works 8-8-2013 Siloles Bearing Coordination-Active 2,5-Substituents: Synthesis, Reactivity, Structural and Spectral Properties. James Bryan Carroll University of Missouri-St. Louis, [email protected] Follow this and additional works at: https://irl.umsl.edu/dissertation Part of the Chemistry Commons Recommended Citation Carroll, James Bryan, "Siloles Bearing Coordination-Active 2,5-Substituents: Synthesis, Reactivity, Structural and Spectral Properties." (2013). Dissertations. 285. https://irl.umsl.edu/dissertation/285 This Dissertation is brought to you for free and open access by the UMSL Graduate Works at IRL @ UMSL. It has been accepted for inclusion in Dissertations by an authorized administrator of IRL @ UMSL. For more information, please contact [email protected]. Siloles Bearing Coordination-Active 2,5-Substituents: Synthesis, Reactivity, Structural and Spectral Properties. By James B. Carroll II A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy (Chemistry) University of Missouri – St. Louis August 2013 II This is dedicated to my parents, my partner Holly Pope, and all of my family and friends. Your love, encouragement, and support have encouraged me and have kept me going through all my years of learning; the culmination thereof, represented as this document, would have been impossible without you. To many more years of learning! III Acknowledgements I would like to acknowledge here the people who have contributed graciously to the completion of my project and my development as a chemist. I would first like to thank Dr. Janet Braddock-Wilking for her advisement both during my undergraduate and graduate schooling. Through your willingness to help me during my projects when I needed it, and allowing me to work out some of my projects on my own, I now have invaluable experience in designing projects, as well as investigating how to better execute those projects through rigorous analyses; these skills will greatly benefit me through my future endeavors. Moreover, through your friendliness and ease of communication, I could count on you as both an advisor, and a friend. My gratitude goes to my committee for the helpful comments: Dr. Eike Bauer, Dr. Wes Harris, and Dr. Nigam Rath. In particular, Dr. Harris helped me to elucidate a plausible mechanism for metal binding on one of my compounds, and Dr. Rath graciously assisted me in learning many aspects of X-ray crystallography. I would like to thank the following for contributing to my research: Dr. Nigam Rath, Dr. Rensheng Luo, Dr. Rudolph E.K. Winter, Joe Kramer, David Osborn, and Dan Zhou. I also would like to thank the faculty and staff of the Department of Chemistry and Biochemistry for being so helpful and student-oriented; it was the main reason why I chose to continue on into graduate education. I will forever cherish the education and personal support I have received from you. Finally, I would like to thank my family, friends, and my partner Holly Pope, for their love, encouragement, and support, all of which providing me the motivation to succeed and realize my doctoral degree. IV Table of Contents Acknowledgements .................................................................................................... III Table of Contents ....................................................................................................... IV List of Abbreviations .................................................................................................. X Table of Figures ........................................................................................................ XII Chapter 1 Figures .................................................................................................. XII Chapter 2 Figures ................................................................................................ XIII Chapter 3 Figures .................................................................................................. XV Chapter 5 Figures (See Chapter) ........................................................................ XVII Chapter 6 Figures .............................................................................................. XVIII Table of Schemes .................................................................................................. XVIII Chapter 1 Schemes ........................................................................................... XVIII Chapter 2 Schemes ............................................................................................. XIX Chapter 3 Schemes ............................................................................................. XIX Chapter 6 Schemes ............................................................................................. XIX Table of Equations .................................................................................................... XX Chapter 2 Equations .............................................................................................. XX Chapter 3 Equations .............................................................................................. XX Table of Tables ....................................................................................................... XXI Chapter 1 Tables ................................................................................................. XXI V Chapter 2 Tables ................................................................................................. XXI Chapter 3 Tables ................................................................................................. XXI Chapter 5 Tables (See Chapter) ......................................................................... XXII Abstract ................................................................................................................. XXIII Chapter 1. Introduction ................................................................................................ 1 1.1. Synthetic Overview of group 14 metalloles, including siloles. .................... 2 1.1.1. Early synthesis of siloles and other metalloles. ......................................... 2 1.1.2. Synthesis of siloles and precursors from metallacycle intermediates. ...... 4 1.1.3. The Tamao procedure for synthesis of 2,5-aryl-3,4-diphenylsiloles. ........ 5 1.2. The optoelectronics of siloles, and the effect of substitution thereon. ............. 7 1.2.1. Substituents at the 1,1-position. .............................................................. 10 1.2.2. Substituents at the 3,4-position. ............................................................... 11 1.2.3. Substituents at the 2,5-position. ............................................................... 13 1.3. Overview of siloles and their coordination to metal centers. ......................... 15 1.3.1. Siloles and group 14 metalloles as cyclopentadienyl analogues. ............ 15 1.3.2. Platinum centers covalently bound to the 2,5-position of silole. ............ 17 1.3.3. Metal coordination to 2,5-substituents. ................................................... 18 1.4. Overview of the photoinduced charge-transfer effect (PCT). ........................ 21 1.5. Statement of the problem. ............................................................................... 24 1.6. References ....................................................................................................... 25 VI Chapter 2. Results and Discussion – 1,1-disubstituted germoles and germole-like compounds: Structural Characterization and Aggregation-Induced Emission ................. 28 2.1. General Introduction ....................................................................................... 28 2.2. Synthesis and spectral characterization of germoles and their precursors. .... 30 2.2.1 Generation of lithiated compounds for synthesis of germoles. ................ 30 2.2.2. Synthesis and characterization of 1,1-dichloro-2,3,4,5- tetraphenylgermole, G1............................................................................................. 33 2.2.3. Synthesis of 1,1-disubstituted-2,3,4,5-tetraphenylgermoles.................... 35 2.2.4. Preliminary study of coordination of G4 with (COD)PtCl2. ................... 38 2.3. SEM study on the effect of cooling a melt on crystallinity and optical properties....................................................................................................................... 40 2.4. X-ray crystallography of 2,3,4,5-tetraphenyl-1,1-disubstituted germoles. ..... 44 2.4.1. General comments on molecular structures. ............................................ 44 2.4.2. Packing arrangements of the tetraphenylgermoles. ................................. 49 2.5. X-ray crystallography of differently substituted germafluorenes. .................. 53 2.5.1. General comments on molecular structures. ............................................ 53 2.5.2. Packing arrangement of the germafluorenes studied. .............................. 56 2.6. Summary ......................................................................................................... 61 2.7. References ....................................................................................................... 62 Chapter 3. Results and Discussion – Siloles with 2,5-subsituents have coordinative ability, and their interactions with metal cations .............................................................
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