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Viologen Based Electroactive Polymers and Composites for Durable Electrochromic Systems VIOLOGEN BASED ELECTROACTIVE POLYMERS AND COMPOSITES FOR DURABLE ELECTROCHROMIC SYSTEMS Bhushan Gadgil TURUN YLIOPISTON JULKAISUJA – ANNALES UNIVERSITATIS TURKUENSIS Sarja - ser. AI osa - tom. 537 | Astronomica - Chemica - Physica - Mathematica | Turku 2016 University of Turku Faculty of Mathematics and Natural Sciences Department of Chemistry Laboratory of Materials Chemistry and Chemical Analysis Supervised by Professor Carita Kvarnström Adjunct Professor Pia Damlin Department of Chemistry Department of Chemistry University of Turku University of Turku Turku, Finland Turku, Finland Reviewed by Professor Martin Sjödin Associate Professor Tanja Kallio Department of Engineering Sciences Department of Chemistry Uppsala University Aalto University Uppsala, Sweden Espoo, Finland Opponent Dr. Aline Rougier, Deputy Director CNRS, University of Bordeaux Bordeaux, France The originality of this thesis has been checked in accordance with the University of Turku quality assurance system using the Turnitin OriginalityCheck service. ISBN 978-951-29-6449-9 (PRINT) ISBN 978-951-29-6450-5 (PDF) ISSN 0082-7002 (Print) ISSN 2343-3175 (Online) Painosalama Oy - Turku, Finland 2016 ‘‘Knowledge can only be got in one way, the way of experience; there is no other way to know.’’ - Swami Vivekananda 4 Table of Contents TABLE OF CONTENTS LIST OF ORIGINAL PUBLICATIONS ................................................................................... 6 LIST OF OTHER RELATED PUBLICATIONS .................................................................. 7 ABBREVIATIONS ........................................................................................................................... 8 ABSTRACT ........................................................................................................................................ 10 TIIVISTELMÄ ................................................................................................................................. 11 1. INTRODUCTION .................................................................................................................. 12 1.1. Chromogenic materials ....................................................................................................... 13 1.2. Electrochromic materials ................................................................................................... 15 1.3. Electrochromic films and devices ..................................................................................... 17 1.4. Electrochromic performance parameters ........................................................................ 19 1.5. Organic electrochromic materials ..................................................................................... 23 1.6. The viologens ....................................................................................................................... 23 1.7. Type I viologen electrochromes ....................................................................................... 25 1.8. Type II viologen electrochromes ...................................................................................... 26 1.9. Type-III viologen electrochromes .................................................................................... 28 1.10. Viologen functionalized conjugated polymers ............................................................. 29 1.11. Polymeric viologens or Polyviologens ........................................................................... 31 1.12. Hybrid electrochromic composite systems ................................................................... 31 1.13. Viologen based ECDs in market .................................................................................... 33 2. AIMS OF THE THESIS ........................................................................................................ 38 3. MATERIALS AND METHODS ......................................................................................... 39 3.1 Synthesis of monomers ...................................................................................................... 39 3.2 Synthesis of graphene oxide (GO) and its reduction .................................................... 40 3.3 Electrochemical synthesis and characterization of electroactive thin films ............... 41 3.4 Spectroscopic & surface characterization techniques .................................................... 42 3.5 In situ spectroelectrochemical characterization .............................................................. 43 4. RESULTS AND DISCUSSIONS ......................................................................................... 45 4.1. Polyviologen from cyanopyridinium based monomer .................................................. 45 4.2. Polyviologen-reduced graphene oxide (PV-rGO) electrochromic films .................... 47 4.3. Electrosynthesis of viologen cross-linked thiophene copolymer ................................ 49 4.4. Electrosynthesis of polythiophene derivative bearing a pendant viologen ................ 52 4.5. In situ ESR-UV-Vis-NIR spectroelectrochemical studies ............................................ 53 Table of Contents 5 5. CONCLUSIONS AND OUTLOOK .................................................................................. 56 ACKNOLEDGEMENTS .............................................................................................................. 58 REFERENCES ................................................................................................................................ 59 ORIGINAL PUBLICATIONS .................................................................................................... 69 6 List of Original Publications LIST OF ORIGINAL PUBLICATIONS This thesis is based on the following original publications, referred to in the text by their Roman numerals (I-IV). I Bhushan Gadgil, Evgenia Dmitrieva, Pia Damlin, Timo Ääritalo & Carita Kvarnström, Redox reactions in a linear polyviologen derivative studied by in situ ESR/UV-vis-NIR spectroelectrochemistry, Journal of Solid State Electrochemistry 19 (2015), 77–83. II Bhushan Gadgil, Pia Damlin, Markku Heinonen & Carita Kvarnström, A facile one step electrostatically driven electrocodeposition of polyviologen–reduced graphene oxide nanocomposite films for enhanced electrochromic performance, Carbon 89 (2015), 53-62. III Bhushan Gadgil, Pia Damlin, Timo Ääritalo, Jouko Kankare & Carita Kvarnström, Electrosynthesis and characterization of viologen cross linked thiophene copolymer, Electrochimica Acta 97 (2013), 378– 385. IV Bhushan Gadgil, Pia Damlin, Evgenia Dmitrieva, Timo Ääritalo & Carita Kvarnström, ESR/UV-Vis-NIR spectroelectrochemical study and electrochromic contrast enhancement of a polythiophene derivative bearing a pendant viologen, RSC Advances 5 (2015), 42242–42249. The original publications have been reproduced with the permission of copyright holders. Contributions of the Author Paper I-IV: The author did all the experimental work except the synthesis of precursors and wrote the first draft of the manuscripts and finalized it together with co-authors. List of Other Related Publications 7 LIST OF OTHER RELATED PUBLICATIONS Bhushan Gadgil, Pia Damlin, Timo Ääritalo & Carita Kvarnström, Electrosynthesis of viologen cross-linked polythiophene in ionic liquid and its electrochromic properties, Electrochimica Acta 133 (2014) 268–274. Bhushan Gadgil, Pia Damlin, Antti Viinikanoja, Markku Heinonen & Carita Kvarnström, One- pot synthesis of an Au/Au2S-viologen hybrid nanocomposite for efficient catalytic applications, Journal of Materials Chemistry A 3 (2015), 9731–9737. Cecilia Lete, Bhushan Gadgil & Carita Kvarnström, The electrochemistry of copolymer films based on azulene and 3-thiophene acetic acid, Journal of Electroanalytical Chemistry 742 (2015) 30–36. Bhushan Gadgil, Pia Damlin & Carita Kvarnström, Graphene vs. reduced graphene oxide: A comparative study of graphene based nanoplatforms on electrochromic switching kinetics, Carbon 96 (2016) 377-381. Bhushan Gadgil, Pia Damlin, Evgenia Dmitrieva, Timo Ääritalo & Carita Kvarnström, Exploring amide linkage in a polyviologen derivative towards simultaneous voltammetric determination of Pb(II), Cu(II) and Hg(II) ions, Electrochimica Acta 192 (2016) 482-488. 8 Abbreviations ABBREVIATIONS ACN Acetonitrile Ag/AgCl Silver/Silver Chloride CCD Charge-coupled device CCE Composite coloration efficiency CE Coloration efficiency CE Counter electrode CPQ Cyanophenyl paraquat CR Contrast ratio CRT Cathode ray tube CV Cyclic voltammetry CW Continuous-wave DMP 9,10-dimethylphenazine EC Electrochromic ECD Electrochromic device EQCM Electrochemical quartz-crystal microbalance ESR Electron spin resonance EtV Ethyl viologen FTIR Fourier transform infrared FTO Fluorine doped tin oxide GC Glassy carbon GO Graphene oxide GQD Graphene quantum dot HD High definition HV Heptyl viologen IBM International Business Machines Corporation ICI Imperial Chemical Industries ITO Indium Tin oxide KCl Potassium Chloride Abbreviations 9 LCD Liquid crystal display MV Methyl viologen NIR Near Infrared NVS Night Vision Safety OD Optical density OTE Optically transparent electrode PB Prussian blue PBV poly (butyl viologen) PEDOT Poly(3,4-ethylenedioxythiophene) PEDOT:PSS Poly(3,4-ethylenedioxythiophene) polystyrene sulfonate PET Polyethylene terephthalate poly(AMPS) poly(2-acrylamido-2-methyl-1-propanesulfonic acid PV Polyviologen PXV poly(hexyl viologen) rGO reduced graphene oxide SEM Scanning electron microscopy
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