DOCSLIB.ORG

Syntheses and Characterization of Linearly Extended Tropylium Salts As N-Type Organic Semiconductors

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Syntheses and Characterization of Linearly Extended Tropylium Salts As N-Type Organic Semiconductors University of New Hampshire University of New Hampshire Scholars' Repository Master's Theses and Capstones Student Scholarship Fall 2015 SYNTHESES AND CHARACTERIZATION OF LINEARLY EXTENDED TROPYLIUM SALTS AS N-TYPE ORGANIC SEMICONDUCTORS Jinyu Yang University of New Hampshire, Durham Follow this and additional works at: https://scholars.unh.edu/thesis Recommended Citation Yang, Jinyu, "SYNTHESES AND CHARACTERIZATION OF LINEARLY EXTENDED TROPYLIUM SALTS AS N- TYPE ORGANIC SEMICONDUCTORS" (2015). Master's Theses and Capstones. 1038. https://scholars.unh.edu/thesis/1038 This Thesis 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 Master's Theses and Capstones by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, please contact [email protected]. SYNTHESES AND CHARACTERIZATION OF LINEARLY EXTENDED TROPYLIUM SALTS AS N-TYPE ORGANIC SEMICONDUCTORS BY JINYU YANG B.S., Nanchang Hangkong University, 2012 THESIS Submitted to the University of New Hampshire in Partial Fulfillment of the Requirements for the Degree of Master of Science in Chemistry September, 2015 This thesis has been examined and approved in partial fulfillment of the requirements for the degree of Master in Chemistry by: Thesis Director, Glen P. Miller, Professor of Chemistry and Materials Science Arthur Greenberg, Professor of Chemistry Erik Berda, Associate Professor of Chemistry and Materials Science On June 26, 2015 Original approval signatures are on file with the University of New Hampshire Graduate School. ACKNOWLEDGEMENTS First and foremost, I would like to thank my father, De Yang and my mother, Xiuzhen Yan for their endless love, care and support. They were the guardians of the child, guides of the teenager and the advocates of the young man. I never feel afraid and lonely because I know they will always be by my side and supporting me no matter what happens. I would like to thank my advisor, Dr. Glen Miller for his help and support. He was always there to offer suggestions and guidance whenever there was a problem with the project. His encouragement always helped me get over of the frustration of failed experiments. From him I learned how to be a scientific researcher and writer. I would like to thank my committee members, Dr. Arthur Greenberg and Dr. Erik Berda for their help on my research and the time spent on reading my thesis. Their invaluable suggestions on my research lead to many interesting discoveries. I would also like to thank Dr. Charles Zercher, Dr. Richard Johnson, Dr. Sterling Tomellini and Dr. Samuel Pazicni for their enlightening lectures. They helped to set the foundation of my research. Last but not least, I cannot miss the chance to thank all Miller group members, especially Jianyu Zhao, Hao Geng, Yadi Wang and Yanmei Rong. They were always there to help and their company made the stressful graduate career easier. I would also like to thank all the professors and staffs of chemistry department who have helped me during my master study. iii TABLE OF CONTENTS ACKNOWLEDGEMENTS ........................................................................................................... iii LIST OF FIGURES ...................................................................................................................... vii LIST OF SCHEMES.................................................................................................................... viii LIST OF TABLES .......................................................................................................................... x LIST OF NUMBERED STRUCTRUES ....................................................................................... xi ABSTRACT ................................................................................................................................. xiii CHAPTER 1 INTRODUCTION .................................................................................................... 1 1.1 Origin of Organic Semiconductor Materials ......................................................................... 1 1.2 Classification of Organic Semiconductor Materials ............................................................. 2 1.2.1 Conjugated Polymers ...................................................................................................... 2 1.2.2 Small Molecules ............................................................................................................. 2 1.3 p-Type & n-Type Organic Semiconductors .......................................................................... 5 1.4 Application of Organic Semiconductors ............................................................................... 6 1.4.1 Organic Light-emitting Diodes (OLED) ........................................................................ 6 1.4.2 Organic Photovoltaic Devices (OPVs) ........................................................................... 7 1.5 Tropylium Ion Species as a Promising n-Type Organic Semiconductor Material ............... 9 CHAPTER 2 SYNTHESES AND CHARACTERIZATION....................................................... 10 2.1 Proposed Synthetic Route ................................................................................................... 10 2.2 Synthesis of Acenotropones ................................................................................................ 11 iv 2.2.1 Synthesis of Benzotropone ........................................................................................... 12 2.2.2 Synthesis of 2,7-Dimethyl-4,5-benzotropol ................................................................. 15 2.2.3 Synthesis of 4,6-Dimethyl-1,2-benzotropylium Tetrafluoroborate 8 ........................... 17 2.2.4 UV-Vis Spectroscopy Analysis of 8 ............................................................................. 19 2.2.5 Synthesis and UV-Vis Spectroscopy Analysis of 12.................................................... 21 2.2.6 Synthesis and UV-Vis Spectroscopy of 5-benzo-4,6-dimethyl-1,2-benzotropylium tetrafluoroborate 14 ............................................................................................................... 23 2.2.7 Synthesis of 4,6-Dimethyl-5-hydroxyl-1,2-acenotropylium Tetrafluoroborate 15 ...... 25 2.2.8 UV-Vis Spectroscopy Analysis of 15 ........................................................................... 26 2.2.9 Conclusion of Synthesis of Benzotropylium Tetrafluoroborates ................................. 27 2.3 Synthesis of 4,6-Dimethyl-1,2-naphthotropylium Tetrafluoroborate ................................. 28 2.3.1 UV-Vis Spectroscopy of 20 .......................................................................................... 30 2.3.2 Stability Study of 20 ..................................................................................................... 31 2.4 Synthesis of 4,6-Dimethyl-1,2-anthracenotropylium Tetrafluoroborate............................. 33 2.4.1 Synthesis of Anthracene-2,3-dicarboxaldehyde 21 ...................................................... 33 2.4.2 Synthesis of 24.............................................................................................................. 37 2.4.3 UV-Vis Study of 24 ...................................................................................................... 37 2.5 Chapter Conclusion ............................................................................................................. 38 CHAPTER 3 OTHER SYNTHESIZED COMPOUNDS ............................................................. 41 3.1 Synthesis of 2,3;6,7-Diepoxy-2,7-dimethyl-4,5-benzotropone ........................................... 41 v 3.2.1 A New Strategy Synthesis of Substituted Acenes ........................................................ 42 3.2.2 Proposed Mechanism for the Formation of 29 and 30 ................................................. 44 CHAPTER 4 EXPERIMENTAL SECTION ................................................................................ 46 4.1 General Methods ................................................................................................................. 46 4.2 Solvents ............................................................................................................................... 47 4.3 Reagent ................................................................................................................................ 48 4.4 Syntheses ............................................................................................................................. 50 APPENDIX ................................................................................................................................... 66 vi LIST OF FIGURES Figure 1. Polyacetylene. .................................................................................................................. 1 Figure 2. Polypyrrole (left) and Polythiophene (right). .................................................................. 2 Figure 3. Pentacene (left) and Bis(phenylthio)pentacene (right). ................................................... 4 Figure 4. α,ω-Dihexyl-substituted sexithiophene. .......................................................................... 5 Figure 5. Fullerene. ......................................................................................................................... 6 Figure
Load more

Recommended publications
  • Chapter 1 Tropone and Tropolone
    School of Molecular and Life Sciences New Routes to Troponoid Natural Products Jason Matthew Wells This thesis is presented for the Degree of Doctor of Philosophy of Curtin University November 2018 Declaration To the best of my knowledge and belief this thesis contains no material previously pub- lished by any other person except where due acknowledgement has been made. This thesis contains no material which has been accepted for the award of any other degree or diploma in any other university. Signature: Date: i Abstract Malaria is an infectious disease found in humans and other animals, it is caused by a single-cell parasite of the Plasmodium genus with many different substrains. Of these, P. falciparum is the most deadly to humans causing the majority of deaths. Although research into the area of antimalarial compounds is wide spread, few have been devel- oped with new structural features. Cordytropolone 37 is a natural product isolated in 2001 from the insect pathogenic fungus Cordyceps sp. BCC 1681 and has been shown to have antimalarial activity against P. falciparum. It has a structure unrelated to antimalarial com- pounds currently used in therapy. It does not contain a peroxide bridge as with artemisinin 25 or quinoline rings as with chloroquine 22. This unique structure indicates that it could possibly interact with the malaria parasite in a fashion unlike current treatments. In order for cordytropolone to be further developed as a potential treatment, it must first be synthe- sised in a laboratory environment. This study attempts to develop the first total synthesis of cordytropolone. H HO O N O O N O N H H H O O Cl HO O 22 25 37 Figure 0.0.1: Cordytropolone 37 has a unique structure compared to the current common malaria treatments The first method investigated towards the total synthesis of cordytropolone involved an intramolecular Buchner ring expansion.
    [Show full text]
  • Mass Spectrometry : Apparatus
    Mass – Spectrometry Mass spectrometry : Apparatus Mass spectrometry :Aparatus MASS Spectrum of acetophenone Fragment Ions Molecular ion (mass ion) MASS Spectrum of Benzamide Mass spectrometry: Processing steps of the sample 1. Ionization of molecules 2. Fragmentation of ionized molecules 3. Acceleration of ions 4. Analysys of the ions Resolution of mass spectrometer 푀 푀푛 10001 푅 = = = = 10000 Δ푀 푀푛−푀푚 10001−10000 M m Mn H ℎ ∗ 100 ≤ 10 % 퐻 Ion sources • 1. Electron ionization (EI) (Electron Impact) • 2. Chemical Ionization (CI) • 3. Fast Atom Bombardment (FAB) • 4. Laser Desorption (LD) • 5. Matrix-Assisted Laser Desorption Ionization (MALDI) • 6. ElectroSpray ionization (ESI) Electron Ionization (EI) – Ionization Chamber Electron Ionization (EI) What is going on physically? Electron Ionization - Energy of electrons Each electron is associated to a wave whose wavelength λ is given by ℎ λ = 푚 υ where m is its mass, v its velocity and h Planck’s constant. Wavelength is 2.7Å for a kinetic energy of 20 eV and 1.4 Å for 70 eV. Number of ions produced as a function of the electron energy. Advantages of EI 1. Reproducible method 2. High Ionization Efficiency 3. All vaporized molecules can be ionized (non polar and insoluble) 4. Molecular structural information (fragmentation) Disadvantages of EI 1. Only +ve ions are formed 2. Sample has to be volatile 3. Limits to 600Da or less MW 4. Extensive fragmentation Chemical Ionization (CI) 1. Sample is injected in atmosfere of gas (methane, izobutane, ammonia). 2. Gas is ionised by EI method. 3. During the collisions of methane ions with molecules of sample, energy is ransfered, as well as protons is transfered.
    [Show full text]
  • Sc-Homoaromaticity
    This is a repository copy of Modern Valence-Bond Description of Homoaromaticity. White Rose Research Online URL for this paper: https://eprints.whiterose.ac.uk/106288/ Version: Accepted Version Article: Karadakov, Peter Borislavov orcid.org/0000-0002-2673-6804 and Cooper, David L. (2016) Modern Valence-Bond Description of Homoaromaticity. Journal of Physical Chemistry A. pp. 8769-8779. ISSN 1089-5639 https://doi.org/10.1021/acs.jpca.6b09426 Reuse Items deposited in White Rose Research Online are protected by copyright, with all rights reserved unless indicated otherwise. They may be downloaded and/or printed for private study, or other acts as permitted by national copyright laws. The publisher or other rights holders may allow further reproduction and re-use of the full text version. This is indicated by the licence information on the White Rose Research Online record for the item. Takedown If you consider content in White Rose Research Online to be in breach of UK law, please notify us by emailing [email protected] including the URL of the record and the reason for the withdrawal request. [email protected] https://eprints.whiterose.ac.uk/ Modern Valence-Bond Description of Homoaromaticity Peter B. Karadakov; and David L. Cooper; Department of Chemistry, University of York, Heslington, York, YO10 5DD, U.K. Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K. Abstract Spin-coupled (SC) theory is used to obtain modern valence-bond (VB) descriptions of the electronic structures of local minimum and transition state geometries of three species that have been con- C sidered to exhibit homoconjugation and homoaromaticity: the homotropenylium ion, C8H9 , the C cycloheptatriene neutral ring, C7H8, and the 1,3-bishomotropenylium ion, C9H11.
    [Show full text]
  • Non-Empirical Calculations on the Electronic Structure of Olefins and Aromatics
    NON-EMPIRICAL CALCULATIONS ON THE ELECTRONIC STRUCTURE OF OLEFINS AND AROMATICS by Robert H. Findlay, B.Sc. Thesis presented for the Degree of Doctor of philosophy University of Edinburgh December 1973 U N /),, cb CIV 3 ACKNOWLEDGEMENTS I Wish to express my gratitude to Dr. M.H. Palmer for his advice and encouragement during this period of study. I should also like to thank Professor J.I.G. Cadogan and Professor N. Campbell for the provision of facilities, and the Carnegie Institute for the Universities of Scotland for a Research Scholarship. SUMMARY Non-empirical, self-consistent field, molecular orbital calculations, with the atomic orbitals represented by linear combinations of Gaussian-type functions have been carried out on the ground state electronic structures of some nitrogen-, oxygen-, sulphur- and phosphorus-containing heterocycles. Some olefins and olefin derivatives have also been studied. Calculated values of properties have been compared with the appropriate experimental quantities, and in most cases the agreement is good, with linear relationships being established; these are found to have very small standard deviations. Extensions to molecules for which there is no experimental data have been made. In many cases it has been iôtrnd possible to relate the molecular orbitals to the simplest member of a series, or to the hydrocarbon analogue. Predictions of the preferred geometry of selected molecules have been made; these have been used to predict inversion barriers and reaction mechanisms. / / The extent of d-orbital participation in molecules containing second row atoms has been investigated and found to be of trivial importance except in molecules containing high valence states of the second row atoms.
    [Show full text]
  • From Acetic Acid Mp 16142 "C; IR 2630 Cm-' (Brd, OH); 'H NMR 11.22 (Brd S
    4440 J. Org. Chem., Vol. 44, No. 24, 1979 Notes from acetic acid mp 16142 "C; IR 2630 cm-' (brd, OH); 'H NMR Chart I 11.22 (brd s, 1 H, OH),7.72 (m, 2 H) and 7.47 (m, 3 H) (C6H5), 2.10 (5, 3 H, CH3). Anal. Calcd for Cloll,N20Cl: C, 57.57; H, 4.35; N, 13.42; C1, 16.99. Found: C, 57.84; H, 4.43; N, 13.26; C1, 17.02. Vilsmeier Reaction of la. Reaction of la under the conditions above gave, from the ether extract, 27% of 4a, mp 210-11 "C," which was identical with a sample prepared by chlorination of 1 2 3 3,5-diphenylpyrazole with S02C12.5 A = 5.80 A = 3.90 A = 5.34 Neutralization of the basic aqueous solution gave 48% of 3a: mp 191-93 "C (from acetic acid); IR 2650 cm-' (brd, OH), 'H NMR 8.50 (brd, 1 H, OH), 7.15-7.60 (m, 10 H, C6H5). Anal. Calcd for Cl!jH11N20C1: C, 66.55; H, 4.10; N, 10.35. Found: C, 66.67; H, 3.84; N, 10.28. Vilsmeier Reaction of 2b. A solution of 1.7 g (11 mmol) of POCl, in 10 mL of DMF was cooled below 10 "C and treated with 1.74 g (10 mmol) of 2bl. The solution was stirred at room tem- 4 5 perature for 150 min, poured into 100 mL of ice-water, and A = 4.67 A = 3.20 neutralized with NaHC03. The solid was collected, washed with water, and dried to give 1.49 g (77%) of 4b.
    [Show full text]
  • Aspects of Reductive Methods in Organophosphorus Chemistry
    Aspects of Reductive Methods in Organophosphorus Chemistry A Thesis presented to the Faculty of Science of the University of New South Wales in fulfilment for the Degree of Doctor of Philosophy by Neil Donoghue B.Sc. (Hons.), University of Adelaide Department of Organic Chemistry School of Chemistry University of New South Wales May 1998 ii Abstract. This study is concerned with the reductive cleavage of tetracoordinated organophos- + – phorus compounds (either quaternary phosphonium salts R4P X or tertiary phosphine oxides R3P O) with either the naphthalene radical (naphthalenide) anion or lithium aluminium hy- dride in THF solution at room temperature (RT). Part 1 examines the reaction of lithium naphthalenide with both phosphonium salts and phosphine oxides. The reaction was dem- onstrated to cleave phenyl groups from both bis-salts and bis-oxides in the presence of 1,2- ethylene bridges; based upon this, parallel syntheses of either 1,4-diphosphabicyclo[2.2.2]oc- tane or its P,P'-dioxide were attempted by using the commercially available ethane-1,2-bis- (diphenylphosphine) as the starting material in each case. Examination of the products of + – reductive cleavage of the series of benzylphenylphosphonium bromide [PhnP(CH2Ph)4-n] Br (where n = 0 to 3) with lithium naphthalenide leads to the proposal of a mechanism. Part 2 describes hydridic reductions of both quaternary phosphonium salts and ter- tiary phosphine oxides. Examination of the lithium aluminium hydride reduction of qua- 31 ternary phosphonium salts using P-NMR has confirmed tetraorganophosphoranes (R4PH; R = Ph, alkyl) as intermediates in the reaction; in addition, two previously unknown classes – of compounds, the triorganophosphoranes R3PH2 and the tetraorganophosphoranates R4PH2 , were also found to be intermediates.
    [Show full text]
  • Henry Payne Phd Thesis
    SOME STUDIES IN HYDRIDE TRANSFER Henry Arthur Sheldon Payne A Thesis Submitted for the Degree of PhD at the University of St Andrews 1966 Full metadata for this item is available in St Andrews Research Repository at: http://research-repository.st-andrews.ac.uk/ Please use this identifier to cite or link to this item: http://hdl.handle.net/10023/15239 This item is protected by original copyright SOME STUDIES IN HYDRIDE TRANSFER A THESIS PRESENTED FOR THE DEGREE OF DOCTOR OF PHILOSOPHY of THE UNIVERSITY OP ST .ANDREWS ty- HENRY ARTHUR SHELDON PAYNE 1%6 ProQuest Number:10170817 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. ProQuest 10170817 Published by ProQuest LLC (2017 ). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code Microform Edition © ProQuest LLC. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, MI 48106 - 1346 Ik $3^0 ■ WLAHATION ■■ I hereby declare that the following thesis is a record of the results of experiments carried out by me, and further that the thesis is my own composition and has not previously been presented for a higher degree The research was carried out in the Department of Chemistry, St* Salvator’s College in the University of St* Andrews under the direction of Dr, D*H.
    [Show full text]
  • Organic and Medicinal Chemistry
    DO MY ASSIGNMENT SUBMIT Sample: Organic Chemistry - Organic and Medical Chemistry ORGANIC AND MEDICINAL CHEMISTRY INSTRUCTIONS: Answer all questions directly on the original sheets provided here using chemical drawing softwares (copy and paste schemes on this sheet as necessary). 1. Explain whether the ion (1) shown below is aromatic or not (you can assume it is planar if it satisfies all the other requirements for aromaticity): + (1) (3 marks) The ion (1) is aromatic, because it is planar, has a delocalized conjugated π system (arrangement of alternating single and double bonds) and obeys Hückel's Rule – number of π delocalized electrons is 6 (according to Hückel's Rule, number of π electrons must be 4n + 2, where n=0, 1, 2, 3,... for a substance to be aromatic) 2. Compound 2 is an isomer of naphthalene. Compound 2 is found to have a high dipole moment compared to naphthalene, which has no dipole moment. Both compounds are regarded as being aromatic: (2) naphthalene (a) Explain why compound 2 is aromatic and has a high dipole moment. (5 marks) The compound 2 is aromatic, because it is planar, has a delocalized conjugated π system (arrangement of alternating single and double bonds) and obeys Hückel's Rule – number of π delocalized electrons is 10. The compound 2 has a high dipole moment, because it may be regarded as the fusion of the aromatic 6 π-electron cyclopentadienyl anion and aromatic 6 π-electron tropylium cation: 1 WWW.ASSIGNMENTEXPERT.COM DO MY ASSIGNMENT SUBMIT +- In order to achieve the stable aromatic sextet in both rings, one electron from the seven-membered ring is transferred to the five-membered ring.
    [Show full text]
  • Molecular Orbitals and Aromaticity
    CHEMISTRY 2500 Topic #5: Bonding in Organic Molecules Fall 2014 Dr. Susan Findlay Molecular Orbital Theory Review Molecular orbital theory is the most widely used model for bonding in molecules. A molecular orbital (MO) is similar to an atomic orbital (AO) in that it describes the probability of finding an electron in a given region. The difference is that a molecular orbital can be spread across multiple atoms within the same molecule. Atomic orbitals are labelled 1s, 2s, 2p, 3s, 3p, 3d, etc. where the letter (s, p, d or f) indicates the orbital shape: Molecular orbitals are labelled 1σ, 2σ, 1π, 2π, etc. where the Greek letter (σ or π) indicates the orbital symmetry: Molecular orbitals are generated by combining atomic orbitals: 2 Molecular Orbital Theory Review We are usually only interested in the valence electrons of molecules and, therefore, the valence orbitals. To construct a valence molecular orbital diagram: Ignore the core electrons Total number of MOs = Total number of AOs Only AOs of similar energy combine to make LCAO-MOs Only AOs of compatible symmetry combine to make LCAO-MOs: σ-type AOs (no node along the bond axis) make σ MOs π-type AOs (with a node along the bond axis) make π MOs e.g. valence MO diagram for H2 3 Molecular Orbital Theory Review e.g. valence MO diagram for F2 4 Molecular Orbital Theory Review In summary, our approach to building valence MO diagrams is: Identify the valence atomic orbitals from each atom and determine their energy levels (relative energy levels if no values given).
    [Show full text]
  • Benzene Loss from Trityl Cations— a Mechanistic Study
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Elsevier - Publisher Connector Benzene Loss from Trityl Cations— A Mechanistic Study Chagit Denekamp and Moran Yaniv Department of Chemistry and Institute of Catalysis Science and Technology, Technion–Israel Institute of Technology, Haifa, Israel Triarylmethyl cations eliminate substituted benzene in the gas phase, upon activation. The mechanism of this process has been studied using deuterium labeling, substituent effects, and density functional theory calculations. It is shown that this apparently simple dissociation is in fact a complicated stepwise process that involves several consecutive hydride shifts. The combination of experimental evidence and computational results leads to a clear description of transition states and reaction intermediates. (J Am Soc Mass Spectrom 2006, 17, 730–736) © 2006 American Society for Mass Spectrometry riphenylmethane dyes form a very important the most abundant being the formation of a trityl cation. class of commercial dyes with applications in Another characteristic of these EI spectra is the presence Tmany fields [1]. Another function of the of antriph- ion at m/z165 that corresponds to the loss of 78 Da enylmethyl (trityl) groups is their usefulness as labile from the trityl cation of m/z 243. The authors suggest protecting groups in organic synthesis [2]. The thatapplica- the resulting ion of m/z 165 is a 9-fluorenyl cation. tions of trityl groups are based on their unique ability to It is also known that benzhydryl cations can afford an form stabilized cations. This is reflected in the relative analogous ion by the loss of H2 [10].
    [Show full text]
  • And Trisubstituted Azulenes Using a Danheiser Annulation As the Key Step: an Advanced Organic Laboratory Experiment Rebecca M
    Masthead Logo Smith ScholarWorks Chemistry: Faculty Publications Chemistry 10-15-2012 Synthesis of Di- and Trisubstituted Azulenes Using a Danheiser Annulation as the Key Step: An Advanced Organic Laboratory Experiment Rebecca M. Thomas Kevin M. Shea Smith College, [email protected] Follow this and additional works at: https://scholarworks.smith.edu/chm_facpubs Part of the Chemistry Commons Recommended Citation Thomas, Rebecca M. and Shea, Kevin M., "Synthesis of Di- and Trisubstituted Azulenes Using a Danheiser Annulation as the Key Step: An Advanced Organic Laboratory Experiment" (2012). Chemistry: Faculty Publications, Smith College, Northampton, MA. https://scholarworks.smith.edu/chm_facpubs/13 This Article has been accepted for inclusion in Chemistry: Faculty Publications by an authorized administrator of Smith ScholarWorks. For more information, please contact [email protected] Synthesis of Di- and Trisubstituted Azulenes Using a Danheiser Annulation as the Key Step: An Advanced Organic Laboratory Experiment Rebecca M. Thomas and Kevin M. Shea* Department of Chemistry, Smith College, Northampton, Massachusetts 01063, United States ABSTRACT: This three-week experiment provides students with an inquiry-based approach focused on learning traditional skills like primary literature interpretation, reaction design, flash column chromatography, and NMR analysis. Additionally, students address higher order concepts like the origin of azulene’s blue color, the mechanism of the Danheiser annulation (step 1), identification of an unknown
    [Show full text]
  • A Study of 3-Tropylium-1,5-Hexadiene
    W&M ScholarWorks Dissertations, Theses, and Masters Projects Theses, Dissertations, & Master Projects 1998 A Study of 3-Tropylium-1,5-hexadiene Elise Noma Hattersley 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 Hattersley, Elise Noma, "A Study of 3-Tropylium-1,5-hexadiene" (1998). Dissertations, Theses, and Masters Projects. Paper 1539626168. https://dx.doi.org/doi:10.21220/s2-kn8k-0777 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]. A STUDY OF 3-TROPYLIUM-l,5-HEXADIENE 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 Elise Noma Hattersley 1998 l ib r a r y College of William and Mar\ APPROVAL SHEET This thesis is submitted in partial fulfillment of the requirements for the degree of Master of Arts Elise Noma Mattersley Approved, July 1998 mlmilMv u rv f , Kathleen Morgan,, DirectDirector Robert Hinkle, AssistantTrofessfcr n Carey Bagdassarian, Assistant Professor TABLE OF CONTENTS A cknowledgements iv T a b l e o f F ig u r e s v T a b l e o f Sy n t h e t ic S c h e m e s vii A b s t r a c t viii Introduction
    [Show full text]