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Environmental Fullerene Chemistry: Elucidating Critical Reaction Pathways and Resulting Products in the Aqueous Phase Jiewei Wu Washington University in St

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Environmental Fullerene Chemistry: Elucidating Critical Reaction Pathways and Resulting Products in the Aqueous Phase Jiewei Wu Washington University in St Washington University in St. Louis Washington University Open Scholarship Engineering and Applied Science Theses & McKelvey School of Engineering Dissertations Spring 5-15-2016 Environmental Fullerene Chemistry: Elucidating Critical Reaction Pathways and Resulting Products in the Aqueous Phase Jiewei Wu Washington University in St. Louis Follow this and additional works at: https://openscholarship.wustl.edu/eng_etds Part of the Chemistry Commons, Environmental Engineering Commons, and the Environmental Sciences Commons Recommended Citation Wu, Jiewei, "Environmental Fullerene Chemistry: Elucidating Critical Reaction Pathways and Resulting Products in the Aqueous Phase" (2016). Engineering and Applied Science Theses & Dissertations. 167. https://openscholarship.wustl.edu/eng_etds/167 This Dissertation is brought to you for free and open access by the McKelvey School of Engineering at Washington University Open Scholarship. It has been accepted for inclusion in Engineering and Applied Science Theses & Dissertations by an authorized administrator of Washington University Open Scholarship. For more information, please contact [email protected]. WASHINGTON UNIVERSITY IN ST. LOUIS School of Engineering & Applied Science Department of Energy, Environmental & Chemical Engineering Dissertation Examination Committee: John Fortner, Chair Parag Banerjee Daniel Giammar Young-Shin Jun Jaehong Kim Brent Williams Environmental Fullerene Chemistry: Elucidating Critical Reaction Pathways and Resulting Products in the Aqueous Phase by Jiewei Wu A dissertation presented to the Graduate School of Arts & Sciences of Washington University in partial fulfillment of the requirements for the degree of Doctor of Philosophy May 2016 St. Louis, Missouri © 2016, Jiewei Wu Table of Contents List of Figures ..................................................................................................................................v List of Tables ............................................................................................................................... viii Acknowledgements ........................................................................................................................ ix Abstract .......................................................................................................................................... xi Chapter 1 : Introduction ...................................................................................................................1 1.1. Background .............................................................................................................................. 1 1.1.1. Fullerene Structure and Physical Property .................................................................... 1 1.1.2. Fullerene Chemical Reactivity ...................................................................................... 4 1.1.3. Fullerenes in Water ........................................................................................................ 7 1.2. Research Significance ............................................................................................................ 10 1.3. Research Objectives ............................................................................................................... 11 1.4. Overview of Dissertation ....................................................................................................... 12 Chapter 2 : Photo-enhanced Fullerene Solvation in Water: Reactive Oxygen Species Generation and Roles in nC60 Formation Process ............................................................................................15 Abstract ..........................................................................................................................................15 2.1. Introduction ............................................................................................................................ 16 2.2. Materials and Methods ........................................................................................................... 19 2.2.1. Materials ...................................................................................................................... 19 2.2.2. Aqu/nC60 Formation Batch Experiments ..................................................................... 20 2.2.3. Reactive Oxygen Species Concentration Measurement .............................................. 21 2.2.4. Products Characterization ............................................................................................ 24 2.3. Results and Discussion .......................................................................................................... 24 2.4. Conclusions ............................................................................................................................ 39 Acknowledgement .........................................................................................................................40 Chapter 2. Supporting Information ................................................................................................41 Chapter 3 : Photo-Oxidation of Hydrogenated Fullerene (Fullerane) in Water ............................46 ii Abstract ..........................................................................................................................................46 3.1. Introduction ............................................................................................................................ 47 3.2. Materials and Methods ........................................................................................................... 49 3.2.1. Materials ...................................................................................................................... 49 3.2.2. Photo-induced Solvation Experiments ........................................................................ 49 3.2.3. Products Characterization ............................................................................................ 50 3.2.4. Octanol-Water Partition Coefficients Measurements .................................................. 52 3.3. Results and Discussion .......................................................................................................... 52 3.4. Conclusions ............................................................................................................................ 60 Acknowledgements ........................................................................................................................61 Chapter 3. Supporting Information ................................................................................................61 Chapter 4 : Ground State Reactions of nC60 with Free Chlorine in Water ....................................68 Abstract ..........................................................................................................................................68 4.1. Introduction ............................................................................................................................ 69 4.2. Materials and Methods ........................................................................................................... 71 4.2.1. Materials ...................................................................................................................... 71 4.2.2. Chlorination Batch Experiments ................................................................................. 72 4.2.3. Product Characterization ............................................................................................. 73 4.2.4. Octanol-Water Partition Coefficients Measurements .................................................. 75 4.2.5. Aggregation Kinetics ................................................................................................... 76 4.3. Results and Discussion .......................................................................................................... 77 4.4. Conclusions ............................................................................................................................ 88 Acknowledgements ........................................................................................................................89 Chapter 4. Supporting Information ................................................................................................91 Chapter 5 : Photo-enhanced Transformation of Hydroxylated Fullerene (Fullerol) by Free Chlorine in Water ..........................................................................................................................99 Abstract ..........................................................................................................................................99 5.1. Introduction .......................................................................................................................... 100 5.2. Materials and Methods ......................................................................................................... 102 5.2.1. Materials .................................................................................................................... 102 iii 5.2.2. Fullerol (Photo)Chlorination Experiments ................................................................ 103 5.2.3. Product Characterization ........................................................................................... 104 5.2.4. Octanol-water Partition Coefficients Measurement
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