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CHARACTERIZATION of the CAROTENOID CIS-BIXIN By CHARACTERIZATION OF THE CAROTENOID CIS-BIXIN by SEFADZI TAY-AGBOZO SHANE C. STREET, COMMITTEE CHAIR MICHAEL K. BOWMAN STEPHEN A. WOSKI SHANLIN PAN MARK WEAVER A DISSERTATION Submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Department of Chemistry in the Graduate School of The University of Alabama TUSCALOOSA ALABAMA 2018 Copyright Sefadzi Tay-Agbozo 2018 ALL RIGHTS RESERVED ABSTRACT Bixin, a carotenoid found in annatto, Bixa orellana, is unique among natural carotenoids by being sparingly water-soluble. Bixin free radicals have been stabilized on the surface of silica alumina and TiO2 and characterized by pulsed electron nuclear double resonance (ENDOR). Least-square fitting of experimental ENDOR spectra calculated from density functional theory (DFT) calculations hyperfine couplings characterized the radicals trapped on silica alumina and TiO2. DFT predicts that the trans bixin radical cation is more stable than the cis bixin radical cation by 1.26 kcal/mol. While this small energy difference is consistent with the 26% trans and 23% cis radical cations in the ENDOR spectrum for silica alumina, the TiO2 spectrum could not be fitted due to poor signal. The ENDOR spectrum for silica alumina shows several neutral radicals formed by loss of a H+ ion from the 9, 9′, 13, or 13′ methyl group, a common occurrence in all water-insoluble carotenoids studied in literature. In addition, the continuous wave (CW) electron paramagnetic resonance (EPR) spectroscopy signal of bixin on silica alumina was intense prior to irradiation. Upon irradiation, the intensity is reduced 4-fold. On the other hand, unlike on TiO2 there was no signal prior to irradiation but signal was observed upon irradiation. The extinction coefficient bixin in chloroform is determined to be 1.1 x 105 ± 0.49 and 1.0 x 105 M-1cm-1 ±0.05 at 472 and 503 nm, respectively, while the redox potential in THF is found to be 0.94 ± 0.01V by cyclic voltammogram (CV) measurements. Based on the irreversibility of the CV, the bixin radical cation is estimated to have a short lifetime and decay rapidly at ambient temperature. ii DEDICATION This thesis is dedicated first to “Mawugã Sogbolisa, Mawugã Kitikata” for bringing me this far, notwithstanding the challenges along the way. I also wish to dedicate my dissertation to my deceased parents wherever they may be. To my parents, I say “Mia dzudzɔ lɛ ŋtifafa mɛ”. To God be the glory! iii LIST OF ABBREVIATIONS AND SYMBOLS AGUI Ampac graphic user interface ~ Approximately Ast Astaxanthin Ast•+ Astaxanthin radical cation B3LYP Becke, 3-parameter, Lee-Yang Parr Bx Bixin Bix•+ Bixin radical cation BET Brunauer-Emmett-Teller Car Carotenoid Car•+ Carotenoid radical cation dye+ Cation of a dye molecule ∆E Change in energy Bix cis-bixin CW Continuous wave CE Counter electrode CV Cyclic voltammogram T Temperature iv DMC Dense memory cluster DFT Density functional theory calculations CDCl3 Deuterated chloroform DCE Dichloroethane DCM Dichloromethane DRIFT Diffusion reflectance infrared Fourier transform spectroscopy DSSC Dye sensitized solar cell e- Electron Electron injected into TiO2 Electron migration to platinum ENDOR Electron nuclear double magnetic resonance spectroscopy EPR Electron paramagnetic resonance ESR Electron spin resonance ESI Electron spray ionization ET Electron transfer dye* Excited dye molecule FTIR Fourier transform infrared spectroscopy ν Frequency of light HeNe laser Helium-neon laser HPLC High performance liquid chromatography hr. Hour IR Infrared v K Kelvin LUMO Lowest unoccupied molecular orbital MS Mass spectrometry L Microliter Micromolar mT Millitesla MCM-41 Mobile crystalline material N3 N3 dye nm Nanometer NMR Nuclear magnetic resonance spectroscopy OTEC Ocean Thermal Energy Conversion VOC Open circuit voltage PSII Photosystem II h Planck’s constant PCE Power conversion efficiency [Bix-H]• Proton loss bixin neutral radical [Car-H]• Proton loss neutral radical [Ast-H]• Proton loss neutral radical of astaxanthin RF Radio frequency RF Reference electrode RT Room temperature RT-DLaTGS Room temperature deuterated L-alanine doped triglycine sulfate ISC Short circuit current vi SiAl Silica alumina SiGel Silica gel STDV Standard deviation τ Tau TW terawatt TWyr Terawatt year TWyr/yr Terawatt year per annum TBAHFP Tetrabutylammonium hexafluorophosphate THF Tetrahydrofuran TGA Thermogravimetric analysis TLC Think layer chromatography TCO Transparent conducting oxide TFA Trifluoracetic acid TZP Triple zeta polarization TEAC Trolox equivalent antioxidant activity UV-vs Ultra violet-visible spectroscopy Vio•+ Vioxanthin radical cation WE Working electrode yr Year [Zea-H]• Zeaxanthin neutral radical Zea•+ Zeaxanthin radical cation vii ACKNOWLEDGEMENTS My deepest appreciation to my advisor and chair of my committee, Dr. Shane C. Street and co-advisor Dr. Michael L. Bowman for their invaluable support, guidance, unceasing encouragement and above all, their patience. I am also extremely grateful for the everyday pep talk and constant reminder from Dr. Lowell Kispert. To say I have been very fortunate to have these great people bother from all three sides to enable me to get this far, is an understatement. Jah Know! I would like to express my profound gratitude members of my committee, Dr. Shanlin Pan, Dr. Stephen A. Woski and last but not the least, Dr. Martin Weaver for their invaluable probing questions and suggestions which enable me to do a comprehensive work. I can’t say how indebted I am to my present and past group members in the persons of Dr. Matthew Krzyaniak, Dr. Preethi Vennam, Dr. Adam Magyar, Dr. Alex Cruce, Dr. Clifton Coushatta Watkins, Mr. Gregory Dye, Dr. Chen Hanjiao, Molly Lockhart, Benjamin Fowler, and Matthew Confer. I am blessed to have met these guys, work alongside and learn from them. I wonder how much progress I would have made without all these awesome guys. I am very indebted to Molly Lockhart and Dr. Rosina Foli for doing most of the proof reading. I want to acknowledge the Department of Chemistry at The University of Alabama for giving me the opportunity and financial support to enable me to pursue my degree. I would also like to thank the Chemical Sciences, Geosciences, and Biosciences Division, Office of Basic Sciences, U.S Department of Energy Grant DE-FG02-86ER-13465, National Science Foundation viii for EPR Instrument Grants CHE-0342921 and CHE-0079498 to UA and the Alabama Supercomputer Center. Last but not the least, I wish to thank my friends and family for their love and continuous support, most especially Dr. Trupti V. Kotbagi. ix CONTENTS ABSTRACT .................................................................................................................................... ii DEDICATION ............................................................................................................................... iii LIST OF ABBREVIATIONS AND SYMBOLS .......................................................................... iv ACKNOWLEDGEMENTS ......................................................................................................... viii LIST OF TABLES ....................................................................................................................... xvi LIST OF FIGURES .................................................................................................................... xvii LIST OF SCHEMES................................................................................................................... xxii CHAPTER 1 INTRODUCTION ................................................................................................... 1 1.1 Energy ..................................................................................................................... 1 1.1.1 Global Energy Demand and Supply ........................................................... 1 1.1.2 The Sun and Solar Energy .......................................................................... 2 1.2.1 Dye Sensitized Solar Cell .............................................................................. 3 1.2.1.1 DSSC Operation.............................................................................. 3 1.2.1.2 Challenges of DSSC ....................................................................... 5 1.2.1.3 Background ..................................................................................... 6 1.2.1.4 The Ideal Sensitizer......................................................................... 6 1.2 Bixin ...................................................................................................................... 10 1.3.1 Background .................................................................................................. 10 x 1.3.2 Annatto ......................................................................................................... 11 1.3.3 Carotenoids .................................................................................................. 13 1.3.3.1 Number of Conjugated Double Bond System and Color of Carotenoids ............................................................................................... 13 1.3 Titanium dioxide ................................................................................................... 15 1.4.1 TiO2 and Photocatalysis ............................................................................... 16 1.4 Silica Alumina .....................................................................................................
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