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Spectroscopic Characterization and Bioanalytical Applications of Benzophenoxazine Derivatives and the Use of Dyes and Dye-Encaps

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Spectroscopic Characterization and Bioanalytical Applications of Benzophenoxazine Derivatives and the Use of Dyes and Dye-Encaps Georgia State University ScholarWorks @ Georgia State University Chemistry Dissertations Department of Chemistry 5-6-2019 Spectroscopic Characterization and Bioanalytical Applications of Benzophenoxazine Derivatives and the Use of Dyes and Dye- Encapsulated Silica Nanoparticles for Fingerprint Detection Eman Alsolmy Follow this and additional works at: https://scholarworks.gsu.edu/chemistry_diss Recommended Citation Alsolmy, Eman, "Spectroscopic Characterization and Bioanalytical Applications of Benzophenoxazine Derivatives and the Use of Dyes and Dye-Encapsulated Silica Nanoparticles for Fingerprint Detection." Dissertation, Georgia State University, 2019. https://scholarworks.gsu.edu/chemistry_diss/163 This Dissertation is brought to you for free and open access by the Department of Chemistry at ScholarWorks @ Georgia State University. It has been accepted for inclusion in Chemistry Dissertations by an authorized administrator of ScholarWorks @ Georgia State University. For more information, please contact [email protected]. SPECTROSCOPIC CHARACTERIZATION AND BIOANALYTICAL APPLICATIONS OF BENZOPHENOXAZINE DERIVATIVES AND THE USE OF DYES AND DYE-ENCAPSULATED SILICA NANOPARTICLES FOR FINGERPRINT DETECTION by Eman Alsolmy Under the Direction of Gabor Patonay, PhD ABSTRACT The use of benzophenoxazine dyes such as Nile red and Nile blue in various applications has received increasing attention in recent years. Due to the limitations of using the two dyes in aqueous media because of their poor solubility, extensive efforts have been made to synthesize new benzophenoxazine analogues. Therefore, the first part of the work aims to characterize modified structures of benzophenoxazine derivatives as well as Nile red and Nile blue using spectroscopic techniques. The optical properties of the dyes involve the determination of molar absorptivity and quantum yield values as well as photostability studies. The absorbance and emission wavelengths are in the visible and near-infrared region of the electromagnetic spectrum which is the most useful region for bioanalytical applications due to the reduced autofluorescence from biomolecules. The first part also includes the interactions between benzophenoxazine derivatives and human serum albumin. The affinity of the dye to the protein is hydrophobicity- dependent, but other parameters such as steric hindrance and electrostatic interaction play a role too as confirmed by binding constant values. Detection of fingerprints is considered one of the most valuable pieces of evidence in forensic investigations. The second part of the work aims to use benzophenoxazine derivatives for fingerprint detection on porous surfaces. The factors affecting the ability of Nile red and Nile blue derivatives to develop luminescent and visible fingerprints with good background contrast are discussed. The second part also contains the application of silica nanoparticles encapsulating some benzophenoxazine derivatives as well as fluorescein isothiocyanate as fingerprint reagents. The efficiency to develop fingerprints is governed by the nature of the encapsulated dye and organosilicate precursors. INDEX WORDS: Benzophenoxazine derivatives, Nile red, Nile blue, Human serum albumin, Fingerprint detection, Silica nanoparticles SPECTROSCOPIC CHARACTERIZATION AND BIOANALYTICAL APPLICATIONS OF BENZOPHENOXAZINE DERIVATIVES AND THE USE OF DYES AND DYE-ENCAPSULATED SILICA NANOPARTICLES FOR FINGERPRINT DETECTION by Eman Alsolmy A Dissertation Submitted in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in the College of Arts and Sciences Georgia State University 2019 Copyright by Eman Alsolmy 2019 SPECTROSCOPIC CHARACTERIZATION AND BIOANALYTICAL APPLICATIONS OF BENZOPHENOXAZINE DERIVATIVES AND THE USE OF DYES AND DYE-ENCAPSULATED SILICA NANOPARTICLES FOR FINGERPRINT DETECTION by Eman Alsolmy Committee Chair: Gabor Patonay Committee: Gangli Wang Kathryn Grant Electronic Version Approved: Office of Graduate Studies College of Arts and Sciences Georgia State University May 2019 iv DEDICATION I would like to dedicate this dissertation to my husband, Ahmed, and my amazing kids, Ruba and Yousef, who have helped me to achieve my dream and make it real. This dissertation also is dedicated to my parents who have encouraged me to accomplish my degree. v ACKNOWLEDGEMENTS I would like to acknowledge my primary investigator, Prof. Gabor Patonay, first for accepting me to join his research group. I have learned invaluable lessons from his classes and during conducting research. It has been truly an honor to be one of his students. I would like to thank also my committee members, Dr. Gangli Wang and Dr. Kathryn Grant for giving me the chance to share my work with them. Also, I would like to thank Dr. Maged Henary and Mr. Vincent Martinez for providing me with the benzophenoxazine derivatives for my project. In addition, I would like to thank all my labmates I have worked with during this educational journey. Special thank goes to the former Ph.D. student, Dr. Garfield Beckford, for his help and patience when I first joined Patonay’s group. I would like to acknowledge Saudi Arabian Cultural Mission in USA, King Abdulaziz University, and University of Jeddah for the financial support. Last but not least, I thank all my family members who have helped and encouraged me during my journey. vi TABLE OF CONTENTS ACKNOWLEDGEMENTS ............................................................................................ V LIST OF TABLES .......................................................................................................... XI LIST OF FIGURES ...................................................................................................... XII 1 FLUORESCENCE APPLICATIONS RELATED TO DYES ............................... 1 1.1 Introduction ......................................................................................................... 1 1.2 Jablonski diagram ............................................................................................... 2 1.3 General characteristics of fluorescence ............................................................. 3 1.4 Fluorescence quenching applications ................................................................ 5 1.5 Benzophenoxazine dyes....................................................................................... 8 1.6 Dye aggregation ................................................................................................. 12 1.7 Protein labeling .................................................................................................. 15 1.8 Human serum albumin ..................................................................................... 17 1.9 Summary ............................................................................................................ 20 References .................................................................................................................... 22 2 SPECTROSCOPIC CHARACTERIZATION OF BENZOPHENOXAZINE DYES IN SOME SOLVENTS ................................................................................................... 30 2.1 Introduction ....................................................................................................... 30 2.2 Experimental...................................................................................................... 32 2.2.1 Instrumentation ............................................................................................. 32 vii 2.2.2 Chemicals and reagents ................................................................................ 33 2.2.3 Stock solutions preparation .......................................................................... 36 2.2.4 Determination of molar absorptivity ............................................................ 36 2.2.5 Determination of quantum yield................................................................... 37 2.2.6 Photostability studies..................................................................................... 38 2.3 Results and discussion ....................................................................................... 38 2.3.1 Spectroscopic characterization of Nile red derivatives ................................ 38 2.3.2 Spectroscopic characterization of Nile blue derivatives .............................. 42 2.3.3 Photostability studies of benzophenoxazine derivatives .............................. 47 2.4 Conclusions ........................................................................................................ 50 References .................................................................................................................... 52 3 INTERACTION OF BENZOPHENOXAZINE DYES WITH HUMAN SERUM ALBUMIN ................................................................................................................................... 56 3.1 Introduction ....................................................................................................... 56 3.2 Experimental...................................................................................................... 58 3.2.1 Instrumentation ............................................................................................. 58 3.2.2 Chemicals and reagents ................................................................................ 58 3.2.3 HSA binding interaction with benzophenoxazine derivatives ..................... 59 3.2.4 Determination of HSA-dye
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