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Development of Cross-Reactive Sensors Array: Practical i DEVELOPMENT OF CROSS-REACTIVE SENSORS ARRAY: PRACTICAL APPROACH FOR ION DETECTION IN AQUEOUS MEDIA Yuanli Liu A Dissertation Submitted to the Graduate College of Bowling Green State University in partial fulfilment of the requirements for the degree of DOCTOR OF PHILOSOPHY December 2012 Committee: Dr. Pavel Anzenbacher, Advisor Dr. Junfeng Shang Graduate Faculty Representative Dr. Peter Lu Dr. Thomas H. Kinstle ii ABSTRACT Dr. Pavel Anzenbacher Jr., Advisor Chemical sensing platforms that can sensitively, rapidly and accurately detect specific chemical species in various operating media are of great importance, especially in complex aqueous environments. Chemical sensor array coupled with chemometrics methods provide an impressive option for high performance chemical sensing. The efforts of this dissertation focus on the application of fluorimetric sensors array in ions detection in complex aqueous media. This dissertation first presents the various signal transduction mechanisms that involve in optical chemosensor design. The sensing elements are created by embedding chemosensors into polymer matrix, then they are arrayed in microtiter plate containing multiple wells. The chemometrics methods used for analyzing the multivariate signal arising from the sensor array are introduced in detail. In the part of practical application of sensors array. The first work aims to detect ions in water by a simple sensors array contains six off-the shelf chemosensors. It turns out that the sensors array is able to recognize cations, anions and ion-pairs with recognition efficiency (6:35) and higher than 93% classification accuracy in water at a wide range of pH (5-9). Such a high discrimination capacity was generally achieved only with structurally complex chemical sensors. The second work presents a fluorescent sensor array containing eight hydrogen-bonding based chemosensors capable of qualitative and quantitative detecting fourteen carboxylic drugs in water and human urine. PCA and LDA are employed to optimize the size of sensors array. It shows that a simple sensors array containing S5 and S8 can achieve 100% classification in water, and another sensors array containing S5 and S7 can achieve 100% classification in human urine. iii The third work demonstrates a new method for the construction of sensor array by employing the synergy between the chemosensor and polymer matrix. The results of anions and urine samples detection as well as quantitatively NSAIDs detection confirm that the established sensing system possesses the bright prospect in real-world application. iv To my beloved wife v ACKNOWLEDGMENTS The years of pursuing my PhD in the Center of Photochemical Sciences have been the most memorable times for me. There are many great people that I got to know during this period deserve my heartfelt gratitude. In this acknowledgement I would like to first express my sincere gratitude to my advisor Dr. Pavel Anzenbacher Jr. for his consistent inspiration, support and guidance by which made me to grow as a scientist. Thanks to all my Committee members Dr. Junfeng Shang, Dr. Peter Lu and Dr. Thomas H. Kinstle for their continue instruction and for helping me improving and broadening my knowledge. Special thanks to Dr. Arthur S. Brecher for the great help and patience in improving my oral English. I would like to thank all my lab-mates, especially Dr. Tsuyoshi Minami, Dr. Manuel Palacious, Dr. Zhuo Wang, Dr. Cesar Perez, Dr. Lorenzo Mosca, Dr. Grygory Zyryanov, Dr. Dula Man, Dr. Ryota Kabe, Dr. Shin-ya Takizawa and Dr. Marketa Schinkmanova. With whom I have worked with and learnt a lot over the past years. Also, I am thankful to Selin Ergun, Maria Kozelkova, Fereshteh Emami Piri, Alex Orlov, Petr Koutnik, Nina Esipenko, Dustin Theibert, Sachin Vahile, Tanxin Du. It has been my greatest pleasure to collaborated with you and learnt from all of you guys. The incredibly inspiring atmosphere and invaluable friendship created by you guys has made my journey so meaningful and enjoyable. Words fail me to express my heartily appreciation to Nora Cassidy, the coordinator of graduate program in Center for Photochemical Sciences, whose help in various ways walked me through the hardest time. My sincere thanks also goes to Dr. Alexander N. Tarnovsky for his help in PhD course study. The financial support from the Department of Chemistry was also greatly appreciated. vi Special thanks to Wei Xiong, Dan Chen, Sile Wang, Yuan Yao, Lingzhi Yang, Jing Li, Jianxia Zhang, Hongtao Yu, Fei Xie, Xiaodong Liu and other friends who started the same journey and pursuing the same dream as me. I would never feel lonely with your companionship. I must acknowledge Hong Xu couple, Xiaoqun Zhang couple, Zhao Yang couple, Dapeng Zhou couple, Qie Li couple, for your continues support which made my life in Bowling Green filled with happiness. I must acknowledge my family for all the invaluable assistance and cooperation in various aspects of my daily life. Finally, warmest and deepest thanks to my wife Yuexin Chen for her always support, understanding and cares, which allows me getting through the most stressful time. vii TABLE OF CONTENTS CHAPTER I. INTRODUCTION .................................................................................................... 1 1.1 Background ....................................................................................................................... 1 1.2 Optical Chemosensors and Signal Transduction Mechanism ........................................... 3 1.3 Cross-Reactive Sensors Array........................................................................................... 9 1.4 Role of Polymer Matrix in Chemical Sensing ............................................................. 11 1.5 Goals of the Thesis .......................................................................................................... 13 1.6 References ....................................................................................................................... 15 CHAPTER II. SENSORS ARRAY: DETECTION SCHEME AND DATA ANALYSIS ...... 25 2.1 Introduction ..................................................................................................................... 25 2.2 Plate for Sensors Array .................................................................................................. 25 2.3 Detection Schemes of Sensors Array ........................................................................... 26 2.4 Data Acquisition and Instruments................................................................................. 27 2.5 Chemometrics in Data Analysis .................................................................................... 32 2.6 Summary ......................................................................................................................... 35 2.7 References ....................................................................................................................... 35 CHAPTER III. RECOGNITION OF ION PAIRS IN WATER USING A SIMPLE FLUORIMETRIC SENSORS ARRAY ...................................................................................... 39 3.1 Introduction ..................................................................................................................... 39 3.2 Selection of Polymer Matrix ......................................................................................... 40 viii 3.3 Selection of Chemosensors ........................................................................................... 41 3.4 Sensing of Ion-pairs in Water ....................................................................................... 42 3.5 Statistical Analysis of Multivariate Response Patterns ............................................... 45 3.6 Conclusion ...................................................................................................................... 53 3.7 Experimental Section ..................................................................................................... 53 3.8 References ....................................................................................................................... 55 CHAPTER IV. A FLUORIMETRIC SENSORS ARRAY FOR CARBOXYLIC DRUGS DETECTION IN WATER AND URINE ..................................................................................... 60 4.1 Introduction ..................................................................................................................... 60 4.2 Selection of Chemosensors for Preparation of Sensors Array ........................................ 61 4.3 Sensing of Carboxylic Drugs in Water ........................................................................... 64 4.4 Size Optimization of Sensors Array: Exploring the Simplest yet Effective Sensors Array for Carboxylic Drugs in Water…………………………………………………..70 4.5 Discriminatory Capacity of a Single Sensor 4.5 .......................................................... 73 4.6 Sensing of Carboxylic Drugs in Human Urine ............................................................ 74 4.7 Size Optimization of Sensors Array: Exploring the Simplest yet Effective Sensors Array for Carboxylic Drugs in Urine…………………………………………………...78 4.8 Conclusion ...................................................................................................................... 80 4.9 Experimental Section ..................................................................................................... 82 4.10 References ...................................................................................................................
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