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Molecular Engineering of Organic Photosensitizes for P-Type Dye

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Molecular Engineering of Organic Photosensitizes for P-Type Dye Molecular Engineering of Organic Photosensitizes for P-type Dye-Sensitized Solar Cells and the Immobilization of Molecular Catalyst for the Hydrogen Evolution Reaction THESIS Presented in Partial Fulfillment of the Requirements for the Degree Master of Science in the Graduate School of The Ohio State University By Damian Richard Beauchamp Graduate Program in Chemistry The Ohio State University 2016 Master's Examination Committee: Yiying Wu Ph.D., Advisor James Cowan Ph.D. Copyright by Damian Richard Beauchamp 2016 Abstract Solar energy has become an important component in the clean energy mix. There are several different kinds of solar cells that have been developed over decades. The focus of the first three chapters will be p-type dye-sensitized solar cells (DSSCs), which are omnipotent for obtaining high efficiency and cost effective tandem DSSCs. The efficiency of p-type DSSCs lags behind their n-type counterpart due to being less investigated. Herein, the attempts to increase performance of the p-type component via molecular engineering of organic photosensitizers is described. Through the addition of bulky hydrophobic alkyl chains performance can be enhanced, though it was found that the location of these alkyl chains is a critical factor. Additionally, by adopting a double- acceptor single-donor design, as described in chapter 3, when employing the commonly used triphenylamine donor moiety, one can simultaneously increase the molar extinction coefficient while reducing the synthetic steps yielding one the fields top performing photosensitzers. In addition to the conversion of solar energy to electrical energy, the storage of intermittent renewable energy is important. Energy can be stored mechanically (e.g. pumped hydro, fly wheels, compressed air, etc.), electrochemically (e.g. batteries and capacitors), or in chemical bonds (e.g. hydrolysis, carbon dioxide reduction, etc.). Of these methods hydrolysis to produce hydrogen has been identified as an attractive potential method. This is because hydrogen has high specific energy, can be transported, ii and used as a fuel in fuel cells emitting only water. The problem is industry currently employs steam-methane reforming to produce hydrogen, because catalysts currently employed for hydrolysis are expensive (i.e. noble metals) and/or unstable. Therefore finding a more abundant, lower cost, and stable catalyst which can be easily processed has been of importance. Molybdenum disulfide based catalysts have been identified as a good candidate because of their low Gibbs free energy of proton absorption. The molecular variants have the highest density of catalytically active sites, but suffer from desorption from electrode surfaces. Herein a molecular molybdenum disulfide catalyst is immobilized via polymer coordination yielding a catalytic material which can be easily processed into films via a resin. This produced stable catalytic films on electrode surfaces, which show good activity toward hydrogen evolution via water reduction. iii Dedication This document is dedicated to my wife, Cynda Beauchamp, who has supported and dealt with me through my entire academic career. Kallum Beauchamp, my son, who fills my heart with joy and love and who reminds me everyday what really matters. My parents, Richard and Jacqueline Beauchamp, who have supported me and taught me among many other things to be self-motivated, to have levity, and the importance of education. Additionally, I dedicate this thesis to Matthew Heaver for whom I continue to try to make a positive and lasting impact on the world. Last but not least, my great friend, Nathan Stopczynski whom I have known since early childhood and have had a great deal of wonderful adventures with, I will always cherish our enduring friendship. iv Acknowledgments I would like to thank Kevin A. Click for his support, assistance, and hard work, through our undergraduate and graduate careers, especially with the BH. Additionally, I would like to thank Xiaodi Ren and Kate Fisher for all of their hard work developing our start-up company - Kair Battery, it was a wonderful journey. I would like to acknowledge all others in my lab for their assistance and wonderful intellectual contributions. John Bair, Director of the Center of Design and Manufacturing Excellence at The Ohio State University, who helped me develop my natural abilities and taught me a multitude about product/system design, market positioning, cost analysis, pitching, and many other invaluable business related concepts. S. Michael Camp Ph.D., Founder and Executive Director of The Technology Entrepreneurship and Commercialization (TEC) Institute at The Ohio State University's Fisher School of Business, was a wonderful mentor and motivator for me as I was bitten by the 'entrepreneurial bug'. Finally, I would like to thank my advisor, Yiying Wu Ph.D., for allowing the group to follow their imaginations, be creative in their own way, pushing us to do our best work, and funding support. v Vita May 2004 .......................................................Streetsboro High School May 2012 .......................................................B.S. Chemistry, Kent State University 2012 to present ..............................................Graduate Teaching Associate, Department of Chemistry, The Ohio State University Publications 1. Membrane Inspired Acidically Stable Dye-Sensitized Photocathode for Solar Fuel Production. Click, K., Beauchamp, D. R., Huang, Z., Chen, W., and Wu, Y., Journal of the American Chemical Society, 2016, Accepted. 2. An Aqueous Lithium-Iodine Solar Flow Battery for the Simultaneous Conversion and Storage of Solar Energy. Yu, M., McCulloch, W. D., Beauchamp, D. R., Huang, Z., Ren, X., and Wu, Y., Journal of the American Chemical Society, 2015, 137, 8332 - 8335 DOI:10.1021/jacs.5b03626 3. Dye-Sensitized Indium Tin Oxide for High-Current Photocathodes. Huang, Z., He, M., Yu, M., Click, K., Beauchamp, D., and Wu, Y., Angewandte Chemie International Edition, 2015, 54, 1 - 6. DOI: 10.1002/anie.201500274R1 vi 4. Double-Acceptor as a Superior Organic Dye Design for p-Type DSSCs: High Photocurrents and Observed Light Soaking Effect. Click, K.1, Beauchamp, D.1, Garret, B., Haung, Z., Hadad C. M., Wu, Y., PCCP, 2014, 16, 26103 - 26111. DOI:10.1039/c4cp04010d. Fields of Study Major Field: Chemistry vii Table of Contents Abstract ............................................................................................................................... ii Dedication .......................................................................................................................... iv Acknowledgments............................................................................................................... v Vita ..................................................................................................................................... vi Publications ........................................................................................................................ vi Fields of Study .................................................................................................................. vii Table of Contents ............................................................................................................. viii List of Tables .................................................................................................................... xii List of Figures .................................................................................................................. xiii Chapter 1: Introduction into Dye-Sensitized Solar Cells ................................................... 1 1.1 Discovery and Current State ..................................................................................... 1 1.2 Working Principle ..................................................................................................... 2 1.3 P-type DSSCs and Their Importance Towards Tandem DSSCs ............................... 6 1.4 Aqueous DSSCs and New Horizons for Dye-Sensitized Photo-Electrodes ............. 10 Chapter 2 Effect of the Addition of Low-Lying Alkoxy Arm on Solar Cell Performance ........................................................................................................................................... 11 viii 2.1 Introduction ............................................................................................................ 11 2.2 Experimental ........................................................................................................... 13 2.2a Synthesis of novel 4-(bis(4-(5-(2,2-dicyanovinyl)thiophen-2- yl)phenyl)amino)-2-(pentyloxy)benzoic acid (DRB1) and control dye: 4-(bis(4-(5- (2,2dicyanovinyl)thiophen- 2-yl)phenyl)amino)benzoic acid (P1) ........................... 13 2.2b Ultraviolet visible (UV-vis) absorption and emission spectra of DRB1 and P1 ................................................................................................................................... 23 2.2c Solar Cell Fabrication ....................................................................................... 25 2.2d Solar Cell Testing ............................................................................................ 28 2.2f Dye Loading Investigation ................................................................................ 28 2.3 Results and Discussion ............................................................................................ 28 2.3a Synthetic challenges
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