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Conjugated Materials Containing Dithienometalloles Conjugated materials containing dithienometalloles Joshua Paul Green Submitted in partial fulfilment of the requirements for the degree of Doctor of Philosophy in Physics Imperial College London September 2016 Declaration The work presented herein was carried out at the Chemistry Department of Imperial College London between October 2012 and September 2016 under the supervision of Professor Martin Heeney. Except where otherwise stated, all work was performed by me. Joshua P. Green, September 2016 ii Contributions This work would not have been possible without the people below, to whom I send my whole-hearted thanks. The organic field effect transistors discussed in Chapters 2 and 4 were prepared and tested by Dr. Yang Han at Imperial College London. Organic photovoltaic devices (Chapter 3) were tested by Dr. Hyojung Cha and Dr. Pabitra Tuladhar at Imperial College London. The X-ray diffraction measurements in Chapter 2 were carried out by Rebecca Kilmurray at Imperial College London. Photoelectron spectroscopy in air measurements were carried out by Adam Creamer at CSIRO (Melbourne, Australia). Finally, I would like to thank Sam Cryer, Dr. Abby Casey, and Dr. Zhuping Fei for providing starting materials and polymers used in Chapters 2, 3, and 4, respectively. Additional thanks must go to Haojie Dai for his help with the work discussed in Chapter 5 during his time as my student in his Master’s year. iii Copyright Declaration The copyright of this thesis rests with the author and is made available under a Creative Commons Attribution Non-Commercial No Derivatives licence. Researchers are free to copy, distribute or transmit the thesis on the condition that they attribute it, that they do not use it for commercial purposes and that they do not alter, transform or build upon it. For any reuse or redistribution, researchers must make clear to others the licence terms of this work. iv I – Acknowledgements I would first like to thank Professor Martin Heeney for his advice and support over the course of this project – without his support and dedication this PhD would have been infinitely more difficult. The help and guidance he provided me while I pursued my goal of producing the first arsole-containing conjugated polymers was absolutely invaluable, and it has been a pleasure working for him over the past five years. This research would not have been possible without the help of my various collaborators, including Dr. Yang Han, Dr. Hyojung Cha, and Dr. Pabitra Tuladhar who helped with devices, as well as Pascal Cachelin, Rebecca Kilmurray, and Adam Creamer, who performed various measurements on my behalf. I would also like to thank all current and past members of the Heeney and McCulloch groups for their help, advice, and support during my PhD, and for making the lab an enjoyable place to work: Zhuping Fei, Yang Han, Hongliang Zhong, Thomas McCarthy-Ward, Jonathan Marshall, Chin Pang Yau, George Barnes, Abby Casey, Pierre Boufflet, Jess Shaw, Rolf Andernach, Adam Creamer, Iain Andrews, Simeng Wang, Haojie Dai, Brett Baatz, Shengyu Cong, Thomas Hodsden, Adam Marsh, Tingman Wu, Hugo Bronstein, Jenny Donaghey, Christian Nielsen, Bob Schroeder, David James, Iain Meager, Sarah Holliday, Dan Beatrup, Mike Hurhangee, Sam Cryer, Cameron Jellett, Mark Little, Andy Wadsworth, Alex Giovannitti, and Maud Jenart. I was also lucky enough to join the Plastic Electronics Doctoral Training Centre when I first arrived at Imperial College, and I would like to extend my thanks to all the staff and students from that group, in particular those in Cohort 3. Finally, I would like to thank my friends and family for their love and support both before and during this PhD – in particular my parents. You have been absolutely essential for keeping me sane over the last four years, and I could not have done this without you. v II – Abstract The development of new semiconducting conjugated polymers has been an important aspect of plastic electronics research since the early days of the field, as it allows the optoelectronic properties to be tuned for various applications. Dithienometalloles, which consist of a 2,2’-bithiophene fused with a bridging heteroatom, have been an important class of monomers for some time. The heteroatom serves an important role, both in holding the bithiophene unit rigidly coplanar and also in tuning the energetics of the system. In addition, these moieties often possess alkyl chains located on the bridging heteroatom that serve to confer solubility and processability to the final polymers. In this thesis we report the synthesis and properties of a number of dithienometallole- containing polymers, in which the necessary solubilising groups have been moved from the bridging heteroatom to the adjacent thiophene backbone of the dithienometallole. This enabled the preparation of novel, soluble arsole-containing conjugated polymers. These dithienoarsole- containing materials were used in both organic field effect transistors and organic photovoltaic devices, showing promising performances as well as significantly improved air stability over their phosphorus-containing analogues. The effect of changing the bridging heteroatom in dithienometalloles was also studied by comparing the optoelectronic properties and device performances of polymers with carbonyl, silicon, germanium, and nitrogen bridging groups. Finally, dithienopyrrole-based sensors were developed that showed substantial colour changes on exposure to basic solutions, as well as potential for use as readily dopable materials for electronic applications. vi III – Table of contents I – Acknowledgements .......................................................................................................................................... v II – Abstract ................................................................................................................................................................ vi III – Table of contents ............................................................................................................................................ vii IV – List of publications ......................................................................................................................................... xi V – Abbreviations .................................................................................................................................................... xii Chapter 1 – Introduction ...................................................................................................................... 1 1.1 – Organic electronics: a history .................................................................................................. 2 1.2 – Semiconducting polymers ......................................................................................................... 3 1.2.1 – Operating principles ................................................................................................. 3 1.3 – Designing conjugated polymeric systems .......................................................................... 6 1.3.1 – General structure-properties relationships ................................................... 6 1.3.2 – Advantages of bridging ring systems ................................................................ 10 1.3.3 – Dithienometalloles and naming heterocyclic compounds ....................... 12 1.3.4 – Heavy-atom effects ................................................................................................... 14 1.4 – Polymerisation reactions ........................................................................................................... 16 1.5 – Organic field effect transistors ................................................................................................ 18 1.5.1 – Basics and device architectures .......................................................................... 19 1.5.2 – Operating principles and device characteristics .......................................... 19 1.6 – Organic photovoltaics ................................................................................................................. 23 1.6.1 – Operating principles ................................................................................................. 24 1.6.2 – Bulk heterojunction solar cells ............................................................................ 27 1.6.3 – Device characteristics .............................................................................................. 29 1.7 – Scope of the thesis ........................................................................................................................ 31 1.8 – References........................................................................................................................................ 32 Chapter 2 – Arsoles in Organic Field Effect Transistors ........................................................... 37 2.1 – Introduction .................................................................................................................................... 38 2.2 – Synthesis of dithienoarsole monomers ............................................................................... 39 2.2.1 – Preparation of dithienoarsole .............................................................................. 39 2.2.2 – Bromination of dithienoarsole ............................................................................. 41 2.2.2.1 – Oxidation of dibromo-dithienoarsole ...........................................
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