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Branched Poly(Gamma-Stearyl-L-Glutamate). Drew Scott Op Che Louisiana State University and Agricultural & Mechanical College

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Branched Poly(Gamma-Stearyl-L-Glutamate). Drew Scott Op Che Louisiana State University and Agricultural & Mechanical College Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1990 Synthesis and Characterization of Linear and Star - Branched Poly(gamma-Stearyl-L-Glutamate). Drew Scott oP che Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Poche, Drew Scott, "Synthesis and Characterization of Linear and Star -Branched Poly(gamma-Stearyl-L-Glutamate)." (1990). LSU Historical Dissertations and Theses. 5017. https://digitalcommons.lsu.edu/gradschool_disstheses/5017 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. INFORMATION TO USERS The most advanced technology has been used to photograph and reproduce this manuscript from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book. Photographs included in the original manuscript have been reproduced xerographically in this copy. Higher quality 6 " x 9" black and white photographic prints are available for any photographs or illustrations appearing in this copy for an additional charge. Contact UMI directly to order. University Microfilms International A Bell & Howell Information Com pany 300 North Z eeb Road. Ann Arbor, Ml 48106-1346 USA 313/761-4700 800/521-0600 Order Number 9112264 Synthesis and characterization of linear and star-branched poly('-y-stearyl-L-glutamate) Poche, Drew Scott, Ph.D. The Louisiana State University and Agricultural and Mechanical Col., 1990 UMI 300 N. Zeeb Rd. Ann Arbor, MI 48106 Synthesis and Characterization of Linear and Star Branched Poly( 7 -stearyl-L-glutamate) A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The Department of Chemistry by Drew Scott Poche’ B.S., Southeastern Louisiana University, 1984 August 1990 Acknowledgement I would first like to thank my major Professor, Dr. William H. Daly. His dedication and enthusiasm for research, as well as his sharing of an unending supply of knowledge will long be remembered. Also, Professor Paul S. Russo, my minor advisor, deserves special thanks. He initiated the study which became my dissertation topic and was invaluable in the direction of the physical chemistry areas of this research. Thanks also goes to Dr. Frank Fronczek for solving the crystal structure described in Chapter 1. I would also like to thank Dr. Mark McLaughlin, Dr. Dewey Carpenter and Dr. Ezzat Younathan for serving as my committee members. I gratefully acknowledge the financial support of the Louisiana State University Department of Chemistry, a Research Corp. Grant, and the Coates Memorial Fund. I am indebted to Dr. John Vercellotti and Mrs. Sharon Vercellotti for teaching me not only a lot of chemistry but also the importance of honesty and ethics in the chemical profession. I would also like to thank Steve Arnold, Howard Pentes, Dr. Soo Lee, Cecil Geiger, Debbie Tipton, Marrietta Aniano- Ilao and Mazidah Mustafah who supplied much needed friendship, advice and encouragement. Mazidah in particular was quite helpful in orienting me to the various polymer instrumentation used in this work. I would also like to thank my family. My parents have always encouraged me and believed in my abilities and I am grateful for their help. I am also grateful to my wife’s parents who helped us in many ways throughout my time graduate school. I am dedicating this dissertation to Leah, my wife, who is my best friend and has given me unfailing support throughout this work. It is appropriate to acknowledge specifically some individuals who helped with the work in Chapter 4 in light of the unusual way that the work was initiated. Dr. Paul S. Russo was first interested in linear PSLG and initiated the work on this novel polymer by assigning its synthesis and characterization as a project in a graduate polymer course. I was responsible for the synthesis of PSLG and, along with the students of the course, characterization of the polymer. As a result, dn/dc measurements of PSLG were accomplished by Ms. Mazidah Mustafah and Ms. Shoulan Yang. Ms. Mustafah also characterized with light scattering a low molecular weight PSLG. Marietta Aniano-Ilao did some early work on liquid crystallinity; the picture in Figure 4.7 resulted from one of her solutions. Dr. Soo Lee re-measured two Zimm plots. The Zimm plot of Figure 4.17B was obtained from solutions prepared by me and data collected by Dr. Lee. Table of Contents page Acknowledgment ................................................................. ......................... ii List of Tables ................................................................................................. viii List of Figures ................................................................................................ x List of Schemes............................................................................................. xiv List of Abbreviations .................................................................................... xv Abstract.......................................................................................................... xvi Chapter 1: Synthesis of 7 -stearyl-L-glutamate-N-carboxy- anhydride: Application of Bis(trichloromethyl)- carbonate ................................................................................ 1 1.1 Introduction ........................................................................ 2 1.2 Approaches to the Synthesis of 7 -stearyl-L-glutamate 4 1.3 Approaches to the Synthesis of 7 -stearyl-L-glutamate- N-carboxyanhydride (SLGNCA) ............................................. 14 1.4 Summary................................................................................... 20 1.5 Experimental ............................................................................ 21 Chapter 2: Synthesis of Linear Poly(7 -stearyl-L-glutamate) ................. 44 2.1 Introduction .............................................................................. 45 2.2 Synthesis by Amino Initiation ................................................ 47 2.3 Synthesis by Methoxide Initiation ......................................... 51 2.4 Synthesis by Transesterification of PMLG ........................... 54 2.5 Summary................................................................................... 55 iv 2.6 Experimental ............................................................................ 55 Chapter 3: Synthesis of Multi-functional Primary Amino Central Units: Applications to the Synthesis of Star Branched Poly( 7 -steaiyl-L-glutamate) ................................... 82 3.1 Introduction .......................................................................... 83 3.2 Synthesis of Multi-functional Primary Amino Central Units ........................................................................................... 8 6 3.3 Synthesis of Star Branched Poly( 7 -stearyl-L-glutamate) and Poly( 7 -benzyl-L-glutamate) ............................................. 90 3.4 Effect of Methanol in the Polymerization ................. 94 3.5 Summary................................................................................... 96 3.6 Experimental ............................................................................ 96 Chapter 4: Characterization of Poly(nf-stearyl-L-glutamate) ................. 137 4.1 Introduction .............................................................................. 138 4.2 NMR Analysis......................................................................... 141 4.3 Liquid Crystalline Behavior and Differential Scanning Calorimetry ................................................................................ 143 4.4 Gel Permeation Chromatography .................... 156 4.5 Laser Light Scattering ............................................................ 159 Static Light Scattering ............................................................... 159 Dynamic Light Scattering ......................................................... 172 4.6 Summary................................... 180 4.7 Experimental ............................................................................ 180 v Chapter 5: Characterization of Star Branched Poly( 7 -stearyl-L- glutamate) .................................................................................
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