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Synthesis and Characterization of Poly(Carborane-Sulfone)

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Synthesis and Characterization of Poly(Carborane-Sulfone) W&M ScholarWorks Dissertations, Theses, and Masters Projects Theses, Dissertations, & Master Projects 1996 Synthesis and Characterization of Poly(Carborane-Sulfone) Beth Le Ogura College of William & Mary - Arts & Sciences Follow this and additional works at: https://scholarworks.wm.edu/etd Part of the Organic Chemistry Commons Recommended Citation Ogura, Beth Le, "Synthesis and Characterization of Poly(Carborane-Sulfone)" (1996). Dissertations, Theses, and Masters Projects. Paper 1539626050. https://dx.doi.org/doi:10.21220/s2-2pr2-wn69 This Thesis is brought to you for free and open access by the Theses, Dissertations, & Master Projects at W&M ScholarWorks. It has been accepted for inclusion in Dissertations, Theses, and Masters Projects by an authorized administrator of W&M ScholarWorks. For more information, please contact [email protected]. SYNTHESIS AND CHARACTERIZATION OF POLY (C ARBORANE-SULFONE) A Thesis Presented to The Faculty of the Department of Chemistry The College of William and Mary in Virginia In Partial Fulfillment Of the Requirements for the Degree of Master of Arts by Beth Le Ogura 1996 APPROVAL SHEET This thesis is submitted in partial fulfillment of the requirements for the degree of Masters of Arts 0 O w ________ Beth Le Ogura Approved, April 1996 Dr. Richard L. Kiefer Dr. William H. Starnes Dr. Barbara A. Siles In loving memory o f my grandmother, Helen C. Ogura TABLE OF CONTENTS Page ACKNOWLEDGEMENTS......................................................................... viii LIST OF TABLES ............................................................................................. ix LIST OF FIGURES.......................................................................................... xii ABSTRACT ..................................................................................................... xvii INTRODUCTION .......................................................................................... 2 REFERENCES ................................................................................................... 11 CHAPTER II. POLYSULFONES .............................................................. 12 2.1 INTRODUCTION ...................................................................... 12 2.2 TYPE OF POLYMERIZATION................................................ 14 2.3 IDEAL CONDITIONS FOR POLYMERIZATION.............. 18 2.4 MECHANISM~SNAr ................................................................. 19 2.5 EXPERIMENTAL...................................................................... 23 2.6 RESULTS AND DISCUSSION................................................ 26 2.6.1 Molecular Weight C ontrol .......................................... 27 2.7 INSTRUMENTATION USED IN CHARACTERIZATION . 30 2.8 CHARACTERIZATION ........................................................... 34 2.9 CONCLUSION............................................................................ 43 REFERENCES .................................................................................... 44 CHAPTER III. CARBORANES ................................................................. 45 3.1 INTRODUCTION ...................................................................... 45 3.2 HISTORY .................................................................................... 45 3.3 ORIGINS....................................................................................... 46 3.4 NOMENCLATURE AND NUMBERING............................... 47 3.5 STRUCTURE (CLASS).............................................................. 49 3.6 BONDING .................................................................................... 50 3.7 PROPERTIES ............................................................................... 54 3.8 CHARACTERIZATION ........................................................... 57 3.9 DERIVATIVES............................................................................ 59 3.10 CARBORANE POLYMERS...................................................... 59 3.11 USES ....................................................................................... 62 REFERENCES ................................................................... 64 CHAPTER IV. SYNTHETIC APPROACHES.......................................... 67 4.1 INTRODUCTION ...................................................................... 67 4.2 l,2-BIS(HYDROXYMETHYL)-0-CARBORANE................. 69 4.2.1 Characterization ........................................................... 69 4.2.2 Results and Discussion ................................................ 70 4.3 4-CHLOROPHENYL SULFONE............................................. 77 4.4 POLY(CARBORANE-SULFONE) .......................................... 80 4.4.1 STRATEGY 1: POLYCONDENSATION USING THE BHMC MONOMER.......................................... 80 4.4.1.1 Experimental ................................................... 80 4.4.1.2 Characterization ............................................. 82 4.4.1.3 Results and Discussion .................................. 83 4.4.1.4 Conclusion ..................................................... 84 4.4.2 STRATEGY 2: POLYCONDENSATION USING DISODIUM SALT ...................................................... 89 4.4.2.1 Synthesis of the Disodium Salt of Bis(Hydroxymethyl)- 0 -Carborane, Using Sodium Metal and T H F .................... 90 4.4.2.2 Characterization ............................................. 93 4.4.2.3 Results and Discussion .................................. 94 4.4.2.4 Synthesis of the Disodium Salt of Bis(Hydroxymethyl)- 0 -Carborane, Using Sodium Metal and Ether ................. 104 4.4.2.5 Characterization ............................................. 105 4.4.2.6 Results and Discussion .................................. 105 v 4.4.2.7 Conclusion ...................................................... 109 4.4.2.8 Synthesis of the Poly(Carborane-Sulfone), Using the Disodium Salt of BHMC ............................ Ill 4.4.2.9 Characterization ............................................. 113 4.4.2.10 Results and Discussion ............................... 122 4.4.2.11 Conclusion...................................................... 125 4.4.3 STRATEGY 3: PHASE-TRANSFER CATALYSIS 125 4.4.3.1 Experimental ................................................... 130 4.4.3.2 Characterization .......................................... 131 4.4.3.3 Results and Discussion .................................. 140 4.4.3.4 Conclusion...................................................... 141 4.5 THE PHASE-TRANSFER CATALYSIS (PTC) PRODUCT . 143 APPENDIX A 145 4A.1 6,9-BIS(ACETONITRILE)-DECARBORANE.................... 145 4A.1.1 Synthesis and Purification ........................................ 145 4A. 1.2 Characterization ........................................................ 147 4A.1.3 Results and D iscussion ............................................. 147 4A.1.4 Conclusion ................................................................. 149 4A.2 2-BUTYNE-l,4-DIOL DIACETATE..................................... 155 4A.2.1 Esterification of 2-Butyne-l,4-Diol to 2-Butyne-l,4-Diol Diacetate .................................. 156 4A.2.2 Characterization ........................................................ 157 4A.2.3 Results and D iscussion ............................................. 158 4A.2.4 Conclusion ................................................................. 166 4A.3 l,2-BIS(ACETOXYMETHYL)-o-CARBORANE .............. 167 4A.3.1 Synthesis of l,2-Bis(Acetoxymethyl)-Carborane 168 4A.3.2 Characterization ........................................................ 169 4A.3.3 Results and Discussion . ....................................... 170 4A.3.4 Conclusion ................................................................. 172 vi APPENDIX B 176 4B.1 Synthesis of the Disodium Salt of Bisphenol A, Using Sodium Hydride .............................................................. 176 4B.1.1 Characterization ........................................................ 177 4B.1.2 Results and Discussion ............................................ 178 4B.2 Synthesis of the Disodium Salt of Bis(Hydroxymethyl)-o-Carborane, Using Sodium Hydride and THF .......................................... 183 4B.2.1 Characterization ....................................................... 184 4B.2.2 Results and Discussion ............................................ 184 4B.3 Synthesis of the Disodium Salt of Bis(Hydroxymethyl)-c>-Carborane, Using NaH and DMSO ........................................................... 186 4B.3.1 Characterization ....................................................... 186 4B.3.2 Results and Discussion . .................................... 187 REFERENCES .......................................................... 190 CHAPTER VI. CONCLUSION................................................................... 192 5.1 SUM M ARY .................................. 192 REFERENCES .................................................................................... 198 VITA 199 vii ACKNOWLEDGEMENTS The writer wishes to express her appreciation to Professor Richard Kiefer for his support, guidance, and trust throughout this investigation. The author would also like to thank Professors William H. Starnes and Barbara A. Siles for their reading and criticism of this thesis, and for taking the time to serve on her committee. The author also wishes to acknowledge several individuals whose help will not soon be forgotten: Sheeba,
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