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Mesoporous Materials for Dental and Biotechnological Applications Mesoporous Materials for Dental and Biotechnological applications, Curcumin Polymers and Enzymatic Saccharification of Biomass A Thesis Submitted to the Faculty of Drexel University by Indraneil Mukherjee in partial fulfillment of the requirements for the degree of Doctor of Philosophy September 2009 © Copyright 2009 Indraneil Mukherjee. All Rights Reserved. Dedications Dedicated to my parents Ranjan and Rupa Mukherjee for their perennial encouragement and inspiration, my beloved Amelia for her unconditional love and support through the good and bad stretches, and the fond memory of my late grandfathers Bikashindu Mookerji and Surhid Banerjee who would be immensely satisfied with this work. iii Acknowledgments My doctorate studies could not have been completed without the support of numerous individuals and organizations that deserve a special mention. I would like to begin by expressing my immense gratitude towards Drexel University and the Department of Chemistry’s excellent Graduate Teaching Fellowship program for giving me the opportunity to pursue my research so far away from home without any financial burden. I also wish to thank the wonderful staff at the ISSS and GSA for promptly helping me with paperwork formalities, sometimes at very short notice. I am grateful to NIH, Reacta and Greene Tweed & Co. for their generous financial support. It is difficult to find words to express my indebtedness to my advisor, Prof. Yen Wei, who has been a genuine friend, deep philosopher and insightful guide throughout my years at Drexel. I have been very fortunate to have found an advisor who wants his students to be like the ‘Renaissance Man’ and work on multiple and unrelated projects, which I found very useful towards the later stages of my research. I have not only benefitted from his vast scientific knowledge, technical skills and work ethic but have also learned from his completely unique style of personnel management. His enthusiasm for pursuing challenging and significant scientific goals is best summed in his own words “Whatever you do, you have to be, either, the first, the best or the most”. I am also thankful to Dr. Shuxi Li who has been a database of synthetic chemistry “dos and don’ts” and mentored me in the lab, particularly in my first two years. I also appreciate the support of Dr. Solomon Samuel for involving me in the dental materials project and for helping with the mechanical testing. A special recognition must also be made to Dr. Zongtao Zhang for iv sharing with me his expertise on mesoporous materials. I am proud of my collaboration with such excellent scientists. Two people whose unwavering confidence in my abilities merit a special mention are Mr. Tom Hughes and Mr. Colin Murray of Reacta Corporation who have worked extremely hard to provide financial support for the enzyme stabilization projects for Novozymes and US Army. I wish to thank my candidacy and dissertation committee members, Dr. Anthony Addison, Dr. Daniel King, Dr. Sally Solomon, Dr. Robert Hutchins, Dr. Lynn Penn, Dr. Chris Li, Dr. Frank Ji, Dr. Guoliang Yang and Dr. Bradford Wayland, for their valuable time and insightful suggestions which have helped improve the quality of my work. I am obliged to Dr. Kevin Owens for training me on a number of instruments. I am also grateful to all the professors of the Department of Chemistry who have helped me throughout my years at Drexel. I also express my gratitude to Ms. Virginia Nesmith, Ms. Edith Smith, Ms. Tina Lewinski and Mr. Ed Dougherty for their timely assistance. A very special thanks goes to Mr. Thomas Cachaza who has repaired many pieces of glassware on account of my exploits. I shall remember my interactions with past and present graduate students at the Department of Chemistry with the fondest of memories. Mr. James Rieben, Dr. Gordan Reeves, Dr. Guzeliya Korneva, Ms. Adeline Kojtari, Ms. April Holcomb, Mr. Hung Le, Mr. Thomas Measey, Mr. Andrew Hagerman, Mr. Charles Bowman, Mr. Khalid Mirza, Dr. Stephanie Schuster, Ms. Alma Pipic, Mr. Steve Kotovich, Mr. Matthew Rossi, Ms. Renata Szyszka, Dr. Kim Kahle, Mr. Brad Wagner, Dr. Mozhgan Bahadory, Dr. William Erb, Mr. Chris Castillo, Mr. Nick Papadodamis, Ms. Natalie Dixon, Mr. Kyle Hess and many others. I appreciate all your v help and good wishes. I also thank Dr. Tony Wambsgans for his help with several teaching and research related queries. Each and every one of the Wei group students past and present merits a special acknowledgment. Since my first days at Drexel I have always looked towards Dr. Zhengfei Sun, Dr. Houping Yin, Dr. Alpa Patel, Dr. Yi Guo and Dr. Andreas Mylonakis for guidance and I treasure my interaction with these fine researchers. I am also very much appreciative of my collaborative work with Mr. Sudipto Das, Mr. Dave Berke–Schlessel, Mr. Alex Fisher, Ms. Jennifer Chen, Mr. Brett Rosen, Ms. Dalia Sherief, Mr. James Sullivan, Mr. Dan Zumsteg and Mr. Rob Wexler. Mr. Kerry Drake of Greene Tweed & Co., who has been my thermal analysis mentor, merits special thanks for his suggestions and assistance with the collaborative projects. This work would not have been possible without the emotional support and encouragement of my dear fiancée Amelia Martin. She has motivated me through the failures and celebrated in the successes that have marked the progress of my research. It is through her unconditional love that I am now able to match her degree for degree. This section cannot be concluded without expressing my gratitude to my parents Ranjan and Rupa Mukherjee who have been my greatest well wishers throughout life and are very proud of this work. They share my happiness in the successful completion of my doctorate research. I also express my appreciation to my grandmother Ms. Purnima Mookerji and to my late gradparents who would be very proud. Finally, I wish to thank the forces unexplained by science for health and safety during my research at Drexel. vi Table of Contents List of Tables xvi List of Figures xix List of Schemes xxvii List of Symbols xxix List of Abbreviations xxx Abstract xxxiv Chapter 1: Overview of sol-gel mesoporous materials, dental nanocomposites, high temperature, biocompatible and bio–based polymers 1.1. Organization of this dissertation 1 1.2. History and motivation 2 1.3. Synthetic concepts and materials systems 10 1.3.1. The sol–gel process 10 1.3.2. Mesoporous materials 16 1.3.3. Enzyme immobilization 21 1.3.4. Dental nanocomposites 25 1.3.5. Aromatic polysiloxanes for high temperature applications 31 1.3.6. Bio–based polymers and biocompatible polymers 35 1.3.7. Enzymatic degradation of biomass 38 1.4. Analytical and characterization techniques 40 1.4.1. Gas sorption characterization of nanoporosity 41 1.4.2. Dynamic light scattering (DLS) 43 1.4.3. Electron microscopy (SEM, TEM) 44 1.4.4. Thermogravimmetric analysis (TGA) 45 1.4.5. Differential scanning calorimetry (DSC) 46 1.4.6. Gel permeation chromatography (GPC) 46 vii 1.4.7. Mechanical testing 47 1.5. References 70 Chapter 2: Synthesis and characterization of mesoporous zirconia and hybrid mesoporous organosilica using low boiling or sublimable organic compounds as templates 2.1. Introduction 82 2.1.1. Removal of template: a challenge to the development of mesoporous materials 82 2.1.2. Template removal by sublimation: an approach based on template properties 83 2.1.3. Mesoporous zirconia 84 2.1.4. Organic modified mesoporous silica (ormosils) 87 2.2. Experimental section 89 2.2.1. Materials 89 2.2.2. Synthesis of mesoporous zirconia 89 2.2.3. Synthesis of mesoporous vinyl functionalized silica 90 2.2.4. Characterization of mesoporous zirconia 92 2.2.5. Characterization of mesoporous vinyl functionalized silica 93 2.3. Results and discussion 93 2.3.1. Mesoporous zirconia 93 2.3.2. Vinyl functionalized mesoporous silica 98 2.4. Conclusions 100 2.5. Acknowledgment 101 2.6. References 126 Chapter 3: Synthesis and characterization of nonsurfactant templated monodispersed mesoporous silica nanospheres 3.1. Introduction 131 3.1.1. Preparation of size–tunable monodisperse silica spheres by the Stober process 131 3.1.2. Need for monodispersed mesoporous silica spheres 133 viii 3.1.3. Synthesis of monodispersed mesoporous materials 134 3.1.4. Applications of mesoporous silica nano and microspheres 136 3.2. Experimental section 137 3.2.1. Materials 137 3.2.2. Synthesis of mesoporous spheres 137 3.2.3. Characterization 139 3.3. Results and discussion 139 3.3.1. Thermogravimmetric analysis (TGA) 139 3.3.2. Determination of particle size and particle size distribution 140 3.3.3. Determination of textural properties from nitrogen adsorption–desorption isotherms 142 3.3.4. Effect of template content 142 3.3.5. Effect of template type 143 3.3.6. Mechanism of mesopore formation and increase in sphere diameter 144 3.3.7. Effect of heat treatment 145 3.4. Conclusions 146 3.5. References 161 Chapter 4: Protection of enzymes in harsh aqueous media via entrapment in mesoporous sol–gel matrices: single and double encapsulation 4.1. Introduction 167 4.1.1. Enzyme immobilization in mesoporous materials: state of the art 168 4.1.2. Enzymes in detergent applications 172 4.1.3. Savinase: nature of the enzyme 174 4.1.4. Strategy for protection and release 174 4.2. Experimental section 176 4.2.1. Materials 176 4.2.2. Preparation of savinase encapsulated mesoporous silica powders 177 ix 4.2.3. ‘Double encapsulation’ of savinase encapsulated mesoporous silica powders 179 4.2.4. Characterization of savinase encapsulated mesoporous silica powders 180 4.2.5. Assays for determination of enzymatic activity 180 4.2.6. Sample nomenclature 182 4.3.
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