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University of New Hampshire University of New Hampshire Scholars' Repository Doctoral Dissertations Student Scholarship Winter 2000 Diels -Alder reactions between fullerene[60] and various pentacenes James Mack II. University of New Hampshire, Durham Follow this and additional works at: https://scholars.unh.edu/dissertation Recommended Citation Mack, James II., "Diels -Alder reactions between fullerene[60] and various pentacenes" (2000). Doctoral Dissertations. 2147. https://scholars.unh.edu/dissertation/2147 This Dissertation is brought to you for free and open access by the Student Scholarship at University of New Hampshire Scholars' Repository. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced 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 subm itted. 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 comer and continuing from left to right in equal sections with small overlaps. 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. Bell & Howell Information and Learning 300 North Zeeb Road, Ann Arbor, Ml 48106-1346 USA UMI* 800-521-0600 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. DIELS-ALDER REACTIONS BETWEEN FULLERENE[60] AND VARIOUS PENTACENES BY James Mack II B.A. Middlebury College. 1995 DISSERTATION Submitted to the University of New Hampshire in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy In Chemistry December. 2000 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UMI Number 9991558 _UMI ___ UMI Microform9991558 Copyright 2001 by Bell & Howell Information and Learning Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. Bell & Howell Information and Learning Company 300 North Zeeb Road P.O. Box 1346 Ann Arbor, Ml 48106-1346 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. This dissertation has been examined and approved. 9CZ. P- .Dissertation Director. Glen P. Miller. Assistant Professor of Chemistry Richard P. Johnson. Pro(es^or of Chemistry Roy^P^^^ialp^As^^^e1Pr^ss'oTofChemistry ■G JLj <JLa ( a _ - c ( ^ Charles K. Zercher. Associate Professor of Chemistry Olof EKht. Professor of Physics J^) I ^ > 2-<ZfgS ^ Date Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. DEDICATION This dissertation is dedicated to my parents, especially my mother for her undying support in everything I do. Her words of encouragement and love have given me the strength necessary to achieve this honor. iii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGEMENTS First and foremost I would like to thank God for giving me the strength to endure life as a Ph.D chemistry student. I would like to thank my parents James Mack and Lena F. Mack and my brother Vincent E. Mack for giving me support, love and encouragement throughout my tenure as a graduate student. I am in great debt to my fiancee Carol for her understanding, love and her growing patience. I am proud to be able to have shared this experience with her. I would like to thank Allison for giving me the motivation to be successful. I would like to thank my "brother from another mother" Mike, we had this plan since high school. I would like to thank my advisor Glen P. Miller for giving me the guidance and discipline to realize my full potential. I would like to thank the rest of the University of New Hampshire Chemistry Department faculty for providing a wonderful education as well as an excellent work environment. I would like to thank the chemistry department staff especially Cindi and Peggy for bailing me out on many an occasion. I would like to thank members of the Miller group past and present Bill, Gabrielle, Steve, Ingyu, Mark, Julie, Drew and Jon for making all the long and sometimes frustrating hours as enjoyable as can be. I would like to thank past and present University of New Hampshire chemistry graduate students for teaching me the things that are not taught inside the classroom. I would like to thank the Buckyballs; I hope we can win it all one day. I would like to thank the University Instrumentation Center, especially Kathy not only for her NMR advice but also for being a good listener in my most frustrating moments. iv Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. I would like to thank the Graduate School for supporting me and providing a comfortable environment outside of the chemistry department. I would like to thank the New England Board of Higher Education for providing me with financial, moral and emotional support. This is truly one of the best programs with which I’ve been associated. I am proud to have been a NEBHE doctoral scholar. I would like to thank the NEBHE doctoral Scholars especially John and Karielle for enduring New Hampshire with me, providing me with much needed support. I would like to thank non-chemistry graduate students for giving me support and giving me knowledge of material outside of chemistry. I would to thank the Black Student Union for supporting me and keeping me in tune with what was going on outside of Parsons Hall. v Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. TABLE OF CONTENTS D EDICATION...........................................................................................................................iii ACKNOWLEDGEMENTS....................................................................................................iv LIST OF FIGURES...................................................................................................................ix LIST OF SCHEMES................................................................................................................ xii LIST OF TABLES .................................................................................................................... xvi ABSTRACT................................................................................................................................xvii INTRODUCTION..................................................................................................................... 1 A. Fullerene[60] discovery and synthesis ............................................................. 1 1. Physical properties of fullerene[60] ................................................... 4 2. Chemical properties of fullerene[60] .................................................. 9 B. Reactivity of fullerene[60] in cvcloaddition reactions .................................11 1. 1.3-DipoIar additions to fullerene[60] ................................................ 11 2. Diels-Alder cyclizations involving fullerene[60] .............................19 C. Bisadducts of fullerene[60] ..................................................................................24 1. Hirsch nomenclature ................................................................................24 2. Regioselectivity of bisadducts .............................................................. 25 D. Bisfullerene[60] adducts .......................................................................................32 RESULTS AND DISCUSSION ............................................................................................ 37 A. Diels-Alder reactions between fullerene[60] and pentacene ......................37 1. Formation of a C^v monoadduct ........................................................... 37 vi Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. 2. Azabridged pentacenes as precursors to bisfullerene[60] adducts of pentacene ..................................................................................44 3. The formation of bispentacene adducts of fullerene[60] .............61 B. Diels-Alder chemistry between fullerene[60] and 6.13- disubstituted pentacenes ................................................................... 68 1. Calculations and literature precedence ............................................. 68 2. Bisfullerene[60] adducts

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