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Synthesis and Photophysical Studies of Nitrogen Heterocycles Containing Benzothiazines, Benzothiazoles, Indoles and Quinolines

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Synthesis and Photophysical Studies of Nitrogen Heterocycles Containing Benzothiazines, Benzothiazoles, Indoles and Quinolines The University of Maine DigitalCommons@UMaine Electronic Theses and Dissertations Fogler Library Summer 5-2021 Synthesis and Photophysical Studies of Nitrogen Heterocycles Containing Benzothiazines, Benzothiazoles, Indoles and Quinolines Ealin N. Patel University of Maine, [email protected] Follow this and additional works at: https://digitalcommons.library.umaine.edu/etd Part of the Organic Chemistry Commons Recommended Citation Patel, Ealin N., "Synthesis and Photophysical Studies of Nitrogen Heterocycles Containing Benzothiazines, Benzothiazoles, Indoles and Quinolines" (2021). Electronic Theses and Dissertations. 3385. https://digitalcommons.library.umaine.edu/etd/3385 This Open-Access Thesis is brought to you for free and open access by DigitalCommons@UMaine. It has been accepted for inclusion in Electronic Theses and Dissertations by an authorized administrator of DigitalCommons@UMaine. For more information, please contact [email protected]. SYNTHESIS AND PHOTOPHYSICAL STUDIES OF NITROGEN HETEROCYCLES CONTAINING BENZOTHIAZINES, BENZOTHIAZOLES, INDOLES AND QUINOLINES By Ealin Patel B.A. University at Buffalo, 2013 B.S. University at Buffalo, 2013 A DISSERTATION Submitted in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy (in Chemistry) The Graduate School The University of Maine May 2021 Advisory Committee: Matthew Brichacek, Assistant Professor of Chemistry, Advisor Alice E Bruce, Professor of Chemistry Mitchell R. Bruce, Professor of Chemistry William M Gramlich, Associate Professor of Chemistry Michael Kienzler, Assistant Professor of Chemistry Copyright 2021 Ealin Patel ii SYNTHESIS AND PHOTOPHYSICAL STUDIES OF NITROGEN HETEROCYCLES CONTAINING BENZOTHIAZINE, BENZOTHIAZOLE, INDOLE AND QUINOLINE By Ealin Patel Dissertation Advisor: Dr. Matthew Brichacek An Abstract of the Dissertation Presented in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy (in Chemistry) May 2021 Nitrogen heterocycles such as quinolines, benzothiazines, benzothiazoles, and indoles are widely found in nature and these compounds have significance in organic and medicinal chemistry, biochemistry as well as materials science. Monomeric units of eumelanin (brominated 5,6- dimethoxyindolecarboxylate derivatives) were synthesized and regioselectively functionalized to form three monobrominated, three dibrominated, and a tribrominated variant using thermally induced nitrene insertions. After deprotection, three monobrominated 5,6-dihydroxyindole carboxylate (DHICA) derivatives were synthesized, and their UV-Vis absorbance was compared to DHICA. Bominated DHICA derivatives showed similar λmax as DHICA (~330 nm) but did not show aerial oxidation as evident by absence of chromophore absorbance at 550 nm. Monomeric synthetic analogues of pheomelanin subunit benzothiazole (six variants) and benzothiazine (four variants) were synthesized with CO2Et and CH2CN sidechain via Sandmeyer reaction, and Cu (II)- catalyzed thiolation-Ullmann coupling, respectively. This monomeric pheomelanoid synthesis was the first successful unified strategy to access this class of molecules. Utilizing these melanin building blocks, synthesis of mixed melanoids was done using Miyaura borylation and Suzuki- coupling. Preliminary photophysical studies of synthesized mixed melanoids showed red shifted UV absorbance (from ~280 nm to 360 nm) due to extended conjugation and these compounds exhibited fluorescence properties as organic chromophores. With a goal of developing material for optical memory, gold-heli viologen was synthesized and characterized successfully via Pd (0)- catalyzed Stille coupling route, or Hiyama-Heck coupling from 3-bromoquionoline as the key step. Temperature variable photoluminescence and quenching experiments were performed to study the photophysical behavior which showed quenching of gold luminescence by heli-viologen involving an electron transfer. iii DEDICATION Dedicated to my parents, Rupal and Nishid Patel, and my wife Dr. Sutanuka Bhattacharjya for their love, support, and encouragement iv ACKNOWLEDGEMENTS I would like to express my gratitude to my advisor and mentor Dr. Matthew Brichacek for his unwavering support, guidance, patience, and encouragement through my PhD program. Special thanks to our collaborators of the Viologen project, Dr. Howard Patterson, Dr. Aaron Nicholas, and Dr. Robert Arthur for their contributions. I would like to extend my gratitutde to Dr. Mohammad Omary and Dr. Eric Reinheimer for their contributions to this project and the publication. I would like to thank my advisory committee Dr. William Gramlich, Dr. Michael Kienzler, Dr. Mitchell Bruce, and Dr. Alice Bruce for their guidance, advice, and suggestions throughout my PhD work. I would like to thank Dr. Barbara Cole for allowing me to use the photoreactor and LC-MS. This work could not have been completed without the help of David LaBrecque with the instruments. I am grateful to all the current and previous members of Brichacek group specially Billy, Sudeera, Ahmed and Robin. Thank you to all my friends at UMaine, especially Anwesha and Naveen for all the memories and constant encouragement; Nayeem, Grape, Sadie, Suyog, Melissa, and Kyle for making the grad school experience great. Thank you to all my friends from UB-Aishwarya, Yash, and Omkar. I would like to thank my family. My parents, Rupal and Nishid Patel, my sister Aneri, and extended family Neha, Kirit and Vishakha Patel for their support throughout my education and for believing in my success. Finally, thank you to my greatest supporter -my wife Sutanuka who encouraged me to pursue Ph.D. v TABLE OF CONTENTS ABSTRACT ................................................................................................................................... iii DEDICATION ............................................................................................................................... iv ACKNOWLEDGEMENTS .............................................................................................................v LIST OF TABLES ........................................................................................................................ xii LIST OF SCHEMES.................................................................................................................... xiii LIST OF FIGURES ..................................................................................................................... xiv 1 INTRODUCTION .................................................................................................................. 1 1.1 Nitrogen heterocycles ..................................................................................................... 1 1.2 Melanin ........................................................................................................................... 2 1.2.1 Melanogenesis........................................................................................................... 4 1.2.1.1 Rapor-Mason-Prota pathway of Melanogenesis: ..................................... 4 1.2.1.2 Kinetics of melanogenesis ........................................................................ 6 1.2.1.3 Eumelanogenesis ...................................................................................... 8 1.2.1.3.1 Eumelanin structure elucidation: ................................................................... 9 1.2.1.4 Pheomelanogenesis ................................................................................. 11 1.2.1.4.1 Pheomelanin structre elucidation: ............................................................... 14 1.2.1.5 Mixed melanogenesis ............................................................................. 15 1.2.1.5.1 Neuromelanin structure elucidation: ........................................................... 16 1.2.2 Sources and synthesis of Melanins: ........................................................................ 18 vi 1.2.2.1 Extraction: .............................................................................................. 18 1.2.2.2 Chemoenzymatic synthesis: ................................................................... 20 1.2.2.3 Oxidative polymerization: ...................................................................... 21 1.2.2.4 Chemical synthesis of melanin subunits: ................................................ 22 1.2.2.4.1 Synthesis of 5,6-dihydroxyindole carboxylate compounds: ....................... 22 1.2.2.4.2 Synthesis of Eumelanoid oligomers ............................................................ 23 1.2.2.4.3 Synthesis of aminobenzothiazole and 1,4-benzothiazine:........................... 25 1.2.2.4.4 Synthesis of pheomelanoid oligomers: ....................................................... 26 1.2.3 Properties of Melanins: ........................................................................................... 27 1.2.3.1 Physiochemical properties ...................................................................... 27 1.2.3.2 Spectral and Photophysical properties .................................................... 28 1.2.4 Significance and applications: ................................................................................ 31 1.2.4.1 Biological significance: .......................................................................... 31 1.2.4.2 Materials applications: ............................................................................ 32 1.3 Viologens .....................................................................................................................
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