The Spectroscopic Characterization of Newly Developed Emissive Materials and the Effects of Environment on Their Photophysical Properties

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The Spectroscopic Characterization of Newly Developed Emissive Materials and the Effects of Environment on Their Photophysical Properties University of Mississippi eGrove Electronic Theses and Dissertations Graduate School 2015 The Spectroscopic Characterization Of Newly Developed Emissive Materials And The Effects Of Environment On Their Photophysical Properties Louis Edward Mcnamara University of Mississippi Follow this and additional works at: https://egrove.olemiss.edu/etd Part of the Physical Chemistry Commons Recommended Citation Mcnamara, Louis Edward, "The Spectroscopic Characterization Of Newly Developed Emissive Materials And The Effects Of Environment On Their Photophysical Properties" (2015). Electronic Theses and Dissertations. 420. https://egrove.olemiss.edu/etd/420 This Dissertation is brought to you for free and open access by the Graduate School at eGrove. It has been accepted for inclusion in Electronic Theses and Dissertations by an authorized administrator of eGrove. For more information, please contact [email protected]. THE SPECTROSCOPIC CHARACTERIZATION OF NEWLY DEVELOPED EMISSIVE MATERIALS AND THE EFFECTS OF ENVIRONMENT ON THEIR PHOTOPHYSICAL PROPERTIES A DISSERTATION SUBMITTED IN PARTIAL FULFILLMENT OF REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN THE DEPARTMENT OF CHEMISTRY AND BIOCHEMISTRY THE UNIVERSITY OF MISSISSIPPI BY BY LOUIS EDWARD MCNAMARA III DECEMBER 2015 Copyright © 2015 by Louis McNamara All rights reserved ABSTRACT The development of new materials capable of efficient charge transfer and energy storage has become increasingly important in many areas of modern chemical research. This is especially true for the development of emissive optoelectronic devices and in the field of solar to electric energy conversion. The characterization of the photophysical properties of new molecular systems for these applications has become critical in the design and development of these materials. Many molecular building blocks have been developed and understanding the properties of these molecules at a fundamental level is essential for their successful implementation and future engineering. This dissertation focuses on the characterization of some of these newly-developed molecular systems. The spectroscopic studies focus on the characterization of newly-developed molecules based on perylene and indolizine derivatives for solar to electric energy conversion, thienopyrazine derivatives for near infrared (NIR) emissive applications, an SCS pincer complex for blue emissive materials and a fluorescent probe for medical applications. The effects of noncovalent interactions are also investigated on these systems and a benchmark biological molecule trimethylamine N-oxide (TMAO). ii DEDICATION This Dissertation is dedicated to the friends and family that have been at my side and supported me through the years. Especially, my parents Louis and Diane McNamara who always encouraged me to succeed academically and supported me through my academic decisions both emotionally and financially. iii ACKNOWLEDGMENTS First, I would like to acknowledge my advisor Dr. Nathan Hammer for the opportunity to work with him at the University of Mississippi and perform the research outlined in this dissertation. I would also like to acknowledge all of the other professors at the University of Mississippi who have helped guide me to this point, especially my committee members: Dr. Greg Tschumper, Dr. Steven Davis, Dr. Susan Pedigo and Dr. Joseph Gladden. In addition to the University of Mississippi and the professors therein that assisted I would also like to acknowledge Mercer University and the faculty in both the Chemistry and physics departments for preparing for my graduate career. Finally, I would like to acknowledge the funding received from the National Science Foundation (OIA-1539035, EPS-0903787, CHE-0955550, DoEd-GAANN- P200A120046) and the Mississippi Center for Supercomputing Research. iv TABLE OF CONTENTS CHAPTER PAGE ABSTRACT ........................................................................................................................ ii DEDICATION ................................................................................................................... iii ACKKNOWLEDGEMENTS ........................................................................................... iv LIST OF FIGURES ......................................................................................................... viii LIST OF TABLES ............................................................................................................. xi CHAPTER 1: INTRODUCTION ........................................................................................1 1.1 MOLECULAR SPECTROSCOPY ...............................................................................1 1.2 SCATTERING ...............................................................................................................2 1.3 RAMAN SPECTROCOPY ...........................................................................................5 1.4 LUMINESCENCE .......................................................................................................15 1.5 FLUORESCENCE .......................................................................................................17 1.6 NONCOVALENT INTERACTIONS .........................................................................22 CHAPTER 2: EXPERIMENTAL SETUP AND DESIGN ...............................................27 2.1 SCATTERING .............................................................................................................27 2.2 FLUORESCENCE .......................................................................................................30 2.3 FLUORESCENCE QUANTUM YIELDS ..................................................................31 2.4 FLUORESCENCE LIFETIME MEASUREMENTS ..................................................34 v 2.5 DIFFUSE REFLECTANCE ........................................................................................36 2.6 SINGLE MOLECULE SPECTROSCOPY .................................................................37 CHAPTER 3: COMPUTATIONAL MODELING ...........................................................40 3.1 INTRODUCTION TO HARTREE-FOCK..................................................................40 3.2 RECOVERING ELECTRON CORRELATION .........................................................45 3.3 DENSITY FUNCTIONAL THEORY .........................................................................46 CHAPTER 4: CHARACTERIZATION OF MATERIALS FOR SOLAR ENERGY ......48 4.1 MATERIALS FOR SOLAR MATERIALS ................................................................48 4.2 INDOLIZINE BASED DONORS FOR DYE SENSITIZED SOLAR CELLS ..........50 4.3 PERYLENEDIIMIDE-BRIDGED SILSESQUIOXANE NANORIBBONS .............58 4.4 SEMICONDUCTING POLYMER NANOARRAYS .................................................70 4.5 POLY(3-HEXYLTHIOPHENE)-FUNCTIONALIZED SILOXANE NANOPARTICLES ...............................................................................................78 4.6 CONCLUSION ............................................................................................................81 CHAPTER 5: MATERIALS WITH EMISSIVE PROPERTIES ......................................82 5.1 EMISSIVE MATERIALS ...........................................................................................82 5.2 NEAR INFRA-RED EMISSIVE MATERIALS .........................................................83 5.3 OPTICAL CHARACTERIZATION OF A BLUE EMITTING PALLADIUM PINCER COMPLEX .............................................................................................97 5.4 CHARACTERIZATIN OF AFLUORESCENT PROBE ..........................................104 vi 5.5 CONCLUSIONS........................................................................................................110 CHAPTER 6: EFFECTS OF NOCOVALENT INERACTIONS ON SOLID TRIMETHYL AMINE-N OXIDE .......................................................................111 6.1 BIOLOGICAL RELEVANCE AND PREVIOS WORK ..........................................111 6.2 CRYSTAL STRUCTURE .........................................................................................112 6.3 COMPUTATIONAL INVESTIGATION OF CRYSTALLINE TMAO ..................116 6.4 HIGH PRESSURE RAMAN SPECTROSCOPY OF CRYSTALLINE TMAO ......120 6.5 RAMAN UNDER LIQUID NITROGEN (RUNS) ...................................................125 6.6 CONCLUSIONS........................................................................................................127 CHAPTER 7: DEVELOPMENT OF HYBRID SURFACE-GAS PHASE EXPERIMENT ....................................................................................................129 CHAPTER 8: CONCLUSIONS ......................................................................................132 BIBLIOGRAPHY ............................................................................................................135 VITA . ..............................................................................................................................169 vii LIST OF FIGURES FIGURE PAGE 1.3.1 Generic diagram for Raman scattering processes .......................................................5 1.5.1 Diagram for Einstein coefficients .............................................................................18 1.5.2 Diagram of fluorescence ...........................................................................................19 1.5.3 Example chromophore ..............................................................................................22
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