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Synthesis and Electrochemical Study of Aromatic Manganese Carbonyl Complexes and Applications in Hydrogen Storage & Proton

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Synthesis and Electrochemical Study of Aromatic Manganese Carbonyl Complexes and Applications in Hydrogen Storage & Proton Synthesis and electrochemical study of aromatic manganese carbonyl complexes and applications in hydrogen storage & proton reduction catalysis By Wei Dai B.S. Unitersity of Science and Technology of China 2006 A Dissertation Submitted in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in the Department of Chemistry at Brown University Providence, Rhode Island May 2012 © Copyright 2012 by Wei Dai This dissertation by Wei Dai is accepted in its present form by the Department of Chemistry as satisfying the dissertation requirement for the degree of Doctor of Philosophy. Date_____________________ ___________________________________ Dwight A. Sweigart, Advisor Recommended to the Graduate Council Date_____________________ ___________________________________ Shouheng Sun, Reader Date_____________________ ___________________________________ Eunsuk Kim, Reader Approved by the Graduate Council Date_____________________ ___________________________________ Peter Weber, Dean of the Graduate School iii VITA Wei Dai was born on Jan. 12, 1984 in lianyungang, Jiangsu. He attended the USTC from Sep. 2002 to June 2006, graduating with a B. S. in Chemistry Department. He has been a research assistant in Dr. Yi Xie’s lab since summer in 2004, and has co-authored a few publications in peer-reviewed journals. In 2006, he was admitted to the Department of Chemistry of Brown University. In December of 2006, he began to work toward the degree of Doctor of Philosophy in the area of organometallic electrochemistry under the supervision of Professor Dwight A. Sweigart. During this time, he held positions as research and teaching assistant. During his 5 years at Brown, he published 1 paper and 2 more in process. He won the poster price in 2010 of the chemistry department. Right now he is exited about the new discovery of proton couple reduction catalyzed by aromatic manganese complexes. He will continue his academic career as an electrochemist in organometallics. iv Publications at Brown University 1. Wei Dai, Sang Bok Kim, Robert D. Pike, Christopher L. Cahill and Dwight A. Sweigart*. “Electrochemical study of manganese and rhenium arene complexes (C6R6)M(CO)3+ (R= Me, Et)”. Organometallics 2010 29(21), 5173-5178 2. Wei Dai and Dwight A. Sweigart*. “Electrocatalytic proton reduction by aromatic manganese carbonyl complex”. Manuscript in preparation 3. Wei Dai, Robert D. Pike, Dwight A. Sweigart*. “Direct synthesis and characterization of (η6-aniline) manganese tricarbonyl cation and its analogs”. Manuscript in preparation 4. Weibin Li, Gerald Kagan, Huan Yang, Chen Cai, Russell Hopson, Wei Dai, Dwight A. Sweigart and Paul G. Williard*. “Accurate Formula Weight Determination in Physically Separated Systems by Diffusion Coefficient−Formula Weight Correlation”. Organometallics 2010 29(6), 1309-1311 v Acknowledgements First of all, I am grateful to have Dr. Sweigart as my advisor. I knew nothing about organometallics before joining his group, he teached me electrochemistry of organometallics which is a very useful technique. He inspired me with great ideas about new directions of my study. Without his fully support, I could not survive through these five years. Secondly, I would like to express my gratitude to my research committee members: Dr. Sun, I appreciate your kind help as my reference, for your helpful advise in my study; Dr. Suggs and Dr. Kim, I would like to thank you for been my committee in ORP and RPD. And I wish you all the best in the future. Thirdly, I would like to thank Dr. Risen for being my reference. He is truly a nice professor to the chinese community in chemistry department. He phone interviewed me before I came to Brown and teached me advanced inorganic chemistry in my first year. You are truly missed, Bill. Also, I want to thank Lynn, Ginni, Gen, Eric, Allen. Lynn, thank you for being so kind to me. Ginni, thank you for your help for all these five years. Gen, you are missed by the whole department. Even though our group is not a rich group financially, and we haven’t been to many different places for the conferences, but we have been to a few places many many times, and we had our fun as a team in sun valley, davenports, boss’s house. Not many graduate students can really share a life with their advisors, we did and enjoyed it. Boss, to me, you are like a father. You are a person who always has a place in my vi heart for as long as I live. I wish that you have a good health and great happiness in the future. I wish all the students from Sweigart group best luck. Finally, I would like to thank my mom and dad for being there with me whenever I need them. The only thing is, I missed them so much…… vii Abstract of “Synthesis and electrochemical study of aromatic manganese carbonyl complexes and applications in hydrogen storage & proton reduction catalysis” by Wei Dai, Ph.D., Brown University, May 2012. The scope of understanding of aromatic manganese reductive electrochemistry was extended. Five internally connected projects will be introduced. My studies primarily focused on homogeneous and heterogeneous electrochemistry of organomanganese complexes and possible application in electrocatalysis, specifically, proton reduction catalysis. The mechanism of homogeneous reductive electrochemistry of 6 + [(η -HMB)Mn(CO)3] was investigated: it undergoes 1-electron irreversible reduction at room temperature and 2-electron reversible reduction at low temperature. And for the first time, we observed reversibility of 2-electron reduction at room temperature by altering the electrochemical environment. 6 - An important reduction intermediate [(η -HMB)Mn(CO)2] was believed to catalyze proton reduction in strong acidic condition. The proton coupled reduction mechanism was discussed, based on which, optimization of this new class of Mn-catalyst was also proposed. Followed by a different mechanism, polyarene analog, 6 + (η -naphthalene) Mn(CO)3 can be used to transfer and store electric energy to stable “metal hydride” complex and releases the hydrogen when needed. A one-step synthetic method for direct synthesis of (η6-aniline) manganese tricarbonyl cation and its analogs was discovered. The aniline complex is an important precursor for heterogeneous electrochemistry study. The purpose of heterogeneous electrochemistry study is to achieve the reductive electrochemical viii reversibility by covalent attachment of electrode surface with arene manganese tricarbonyl moiety. Physical separation of manganese compound may stop the dimerization after one-electron reduction and result in reductive reversibility. One of my projects is focused on covalent attachment of arene manganese tricarbonyl using diazonium-base chemistry and collecting & analyzing e-chem signal from the surface functionalized electrode. The η6-aromatic manganese dicarbonyl anion is strong nucleophile. It would be interesting to check the reaction between the manganese anion with 6 [(η -HMB)Re(CO)3]PF6. We want to explore the possibility of forming the heterodinuclear dimmer with a novel core structure of Mn-Re metal-metal bond. There is no report about the study of Mn-Re metal-metal bond; furthermore, heterodinuclear complex has potential applications in molecular catalysis. ix Table of contents Chapter 1. Synthesis and electrochemistry study of aromatic manganese carbonyl complexes and their applications in hydrogen storage, proton reduction catalysis: General introduction ································································ 1 1.1 Overview··························································································································2 1.2 Electrochemistry of aromatic manganese carbonyl complex and its analogs ··················3 1.3 Proton reduction catalyzed by aromatic manganese carbonyl complexes ·······················5 1.4 Direct synthesis of (η6-aniline) manganese tricarbonyl cation and its analogs················8 1.5 Surface electrochemistry of aromatic manganese tricarbonyl complexes using diazonium attachment and physical attachment.··································································10 1.6 Synthesis and characterization of heterodinuclear complex with the core structure of Mn-Re metal-metal bond. ····································································································12 1.7 References······················································································································14 Chapter 2. General experiments ················································································ 17 2.1 Inert atmosphere work····································································································17 1. Nitrogen gas ··································································································· 17 2. Air-free technique··························································································· 17 1). Schlenk techniques ···················································································· 17 2). Glove box and Glove bag ·········································································· 17 3). Schlenk line. ······························································································ 18 x 3. Compound Storage ························································································· 18 2.2 Instruments and measurements ······················································································19 1. Liquid infrared spectroscopy
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