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Synthesis and Characterization of Amide and Urea Receptor Systems

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Synthesis and Characterization of Amide and Urea Receptor Systems Synthesis and Characterization of Amide and Urea Receptor Systems for Anion and Metal Complexation and the Synthesis and Use of Block Copolymers for Optoelectronic Crystal Growth By © 2017 Jessica Lohrman Submitted to the graduate degree program in Chemistry and the Graduate Faculty of the University of Kansas in partial fulfillment of the requirements for the degree of Doctor of Philosophy. Chair: Dr. Kristin Bowman-James Dr. Mikhail Barybin Dr. Timothy Jackson Dr. David Benson Dr. Candan Tamerler Date Defended: 28 June 2017 The dissertation committee for Jessica Lohrman certifies that this is the approved version of the following dissertation: Synthesis and Characterization of Amide and Urea Receptor Systems for Anion and Metal Complexation and the Synthesis and Use of Block Copolymers for Optoelectronic Crystal Growth Chair: Dr. Kristin Bowman-James Date Approved: 25 July 2017 ii Abstract The content of this dissertation is divided into two parts, as a result of projects from two research groups during the course of my research at the University of Kansas. The first five chapters detail my work with Dr. Bowman-James which has focused on host-guest chemistry ranging from ligand synthesis to anion and metal binding. I joined the Bowman-James group after my fourth year at KU and have been a member from 2015 to 2017. Ditopic pyrazine pincers or “duplex” pincers were synthesized and investigated for both their anion binding and their metal binding merit. Chapter 2 will investigate duplex hosts as anion binding hosts, the duplex receptors were synthesized with R group functionalizations that permit a range of solubilities in various solvents. Their anion binding capabilities will be discussed in comparison to their monotopic counterparts. The duplex pincers were also studied for transition metal binding capabilities which will be detailed in Chapter 5. Palladium complexes were made and characterized with the duplex pincers and some of the interesting features of these compounds will be discussed. Aside from the duplex hosts, urea macrocyclic receptors were also synthesized and characterized for their anion host capabilities, which will be discussed in Chapter 3. Variations in macrocycle size and urea components were explored and binding merit was determined on these receptor complexes. The final two chapter of this dissertation highlight one of my projects in the Ren group from my first year of graduate school in 2011 up through my fourth year in 2015. I joined the Bowman-James group after Dr. Ren moved to Temple University. Chapter 6 will include a review on the field of organic photovoltaic and optoelectronic devices. Chapter 7 will detail my work synthesizing block copolymers for use as compatibilizing agents for P3HT and C60 iii interfaces. These organic photovoltaic devices exhibited an interesting magnetoconductive behavior that can be observed at room temperature in these charge transfer systems. iv Acknowledgements Firstly, I would like to thank Dr. Bowman-James, from the bottom of my heart, for accepting me into her group after my fourth year. Kristin, you have been the best mentor I could ask for! When working with you, the science is more exciting and there is always something to discuss and figure out. Thank you for always being there when I went through hard times and always helping to pull me through. I will really miss talking to you every day, whether about chemistry or just general ridiculous things. You single handedly restored my appreciation for chemistry and I cannot thank you enough. Dr. Benson, thank you for being a great TA boss! I learned so much about teaching, how to run a classroom, how to construct fair tests, and how to always strive always improve a class from you. I also enjoyed our opera conversations. I cannot thank you enough. My thanks, also, to Tim Jackson and Misha Barybin. Whenever I had a question over the past 6 years, you both would always have an open door and would try to help me out. Thank you Cindy Berrie for helping me with AFM. Rich Givens and Mike Clift, thank you for helping me when I had organic chemistry questions. Victor Day, thank you for all the help with my crystal structures and for the moral support! Thank you Candan Tamerler for agreeing to be on my defense committee. My thanks to the Bowman-James group, both current and former members who have made every day in the lab more fun. Hanumaiah Telikepalli, thank you for the synthetic help and for our small political chats. Sun Ok Kang, than you for helping me with crystal growth and making sense of my endless titration data. Emran Haque, I’m so happy you joined the group, it has been great getting to know you over the past year. Kara Motley, you are a fantastic undergraduate researcher and I know you will be great wherever you end up. v The former Ren group Dan, Alec, and Phil, you guys made every day better. I’ve never laughed harder than when I was with you three and you always stood by me when times were tough, for which, I cannot thank you enough. Though we never knew where our conversations started, we could always be sure it would end with an argument about which teenage mutant ninja turtle villain was the main boss. Dan and Phil: you are still wrong, it’s Shredder. Phil, thank you teaching me spectroscopy and for always having my back. Alec, thank you for having patients when I would be going crazy and for being the best lab mate I could ask for. Dan, I’m still impressed you know all the words to “Let it go”, and I really miss our absurd conversations. I gained three brothers from the Ren group and I am very thankful for that. Thank you to the current and past generations of grad students Hannah, Nate, Chris, Cassie, Jason, Derek, Allyssa, Melissa, Josh, Brad, Theresa, Tom, Indeewara, Pubudu, and Kelci, you are all like family to me. John Meyers and Andy Speath in particular, thank you for mentoring me. John, you make me want to be a better chemist at all times. You also taught me I’m never too old for slip-n-slides, so I’m appreciative for that too. Andy, I’m sorry for glittering your desk. I owe so much to you for all the help and advice you gave me! Mason Hart, you have been one of my best friends here for 5 years. I really don’t know what I’m going to do without game night. Probably be a calmer person since I don’t have to feel like a recess monkey for losing to you every time. Mary Smith, we did this whole thing together, through good times and bad. You’ve supported me so much and I will miss our elaborate dressage dancing. Thank you for making me laugh. Wei Qin, thank you for teaching me about multiferroic materials and for having a good sense of humor. Thank you to Shenqiang Ren for making me a much stronger person and introducing me to materials chemistry. Justin and Sarah, thank you for all the help with NMR vi over the years. My thanks to Simon Lang for helping me whenever I needed help learning new organic set ups. Lastly, I would like to thank my sister Sara and Mom and Dad, without whom I could never have made this far in life. Sara, you are the best role model of a strong women. Nothing can stop you and I’ve always looked up to that. Mom, you brought me from a vaguely illiterate and extremely stubborn 10 year old with poor grades, to a chemistry PhD program. You supported me every time I thought I couldn’t do it, pushed to do better because you knew I could, and then sent me snacks when I wasn’t eating properly. You have always been my emotional rock and biggest fan. I can never finish saying thank you! Dad, you taught me it’s ok to be a bit weird. You’ve supported me this whole time, both financially and emotionally, despite the fact that I’ve been I college 11 years now. Thank you for always making me laugh when I needed it and for always finding new adventures for us to go on! Thank you for believing there was nothing I couldn’t do, and always telling me that my entire life. The three of you mean the world to me and I am thankful every day for each of you. vii Table of Contents Abstract .......................................................................................................................................... iii Acknowledgements… ..................................................................................................................... v Table of Contents… ..................................................................................................................... viii List of Figures… ........................................................................................................................... xii List of Tables… .......................................................................................................................... xvii List of Schemes… ..................................................................................................................... xviii Abbreviations ............................................................................................................................... xxi Chapter 1 – Supramolecular Anion Receptor Review .............................................................. 1 1.0.0 Supramolecular chemistry .................................................................................................. 2 1.1.0 Importance of anions ........................................................................................................... 4 1.2.0 Anionic hosts… .................................................................................................................. 5 1.2.1 Early anionic
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