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Indigoid Molecular Motors and Switches

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Indigoid Molecular Motors and Switches Dissertation zur Erlangung des Doktorgrades der Fakultät für Chemie und Pharmazie der Ludwig-Maximilians-Universität München Indigoid Molecular Motors and Switches Ludwig Alexander Huber aus Pfarrkirchen, Deutschland 2019 Erklärung Diese Dissertation wurde im Sinne von § 7 der Promotionsordnung vom 28. November 2011 von Herrn Dr. Henry Dube betreut. Eidesstattliche Versicherung Diese Dissertation wurde eigenständig und ohne unerlaubte Hilfe erarbeitet. München, den 18.12.2018 ........................ Ludwig Huber Dissertation eingereicht am 18.12.2018 1. Gutachter: Dr. Henry Dube 2. Gutachter: Prof. Dr. Oliver Trapp Mündliche Prüfung am 31.01.2019 Danksagung Ich möchte mich bei Dr. Henry Dube bedanken, dass er mir die Chance bot meine Doktorarbeit auf seinem Forschungsgebiet anzufertigen. Es waren spannende und kenntnisreiche Jahre, die ich nicht so schnell vergessen werde. Bei Prof. Dr. Oliver Trapp bedanke ich mich für die Übernahme des Koreferats. Bei meinen lieben Kollegen Dr. Sandra Wiedbrauk, Aaron Gerwien, Stefan Thumser, Thomas Bartelmann, Nicolai Bach, Florian Kink, Monika Schildhauer, Kerstin Hoffmann, Dr. Manuel Güntner, Christian Petermayer und Edgar Uhl möchte ich mich im Besonderen bedanken, dass sie mir mit Rat und Tat zur Seite standen. Eine solch kollegiale Atmosphäre, wie sie in unseren Laboren herrscht, ist nicht selbstverständlich. Lustig war es immer. Allerdings kam der Orangensaft dann doch nie durch die Nase. Das muss wohl die zukünftige Generation übernehmen. Die Chancen stehen 60/60 würde ich sagen. Ich danke Thomas Bartelmann für die geistreichen Gespräche, die die unendlichen Zeitschleifen so mancher Säule in die Knie zwangen. Thomas, die Lottomillion werden kommen! Der Mann, der seinen Namen schneller wechselt als ein Oktopus sein prächtiges Farbenkleid, brachte mir die theoretische Chemie näher und unterstützte meine Projekte mit seiner Dual-Core Power. Dafür ein herzliches Dankeschön. Dank an Dr. Peter Mayer für die hervorragende Arbeit in der Kristallstrukturanalyse. Bei allen Mitarbeitern des Departements. Ohne eure Arbeit geht es nicht. Besonderer Dank gilt Brigitte Breitenstein, David Stephenson, Sonja Kosak, Claudia Ober, Petra Keilholz, Susanne Sauerer, Robert Eicher, Heidi Buchholz und Michael Gayer. Bei Kerstin Hoffmann möchte ich mich für die super Zusammenarbeit bei unserem gemeinsamen Projekt bedanken. Ebenso bei Roland Wilcken, weil er Spektren schneller misst als sein Schatten. Unsere Kooperation trug viele Früchte und brachte so manche überraschende Erkenntnis. Ebenfalls bedanke ich mich bei Prof. Dr. Eberhard Riedle für die Zusammenarbeit bei unseren Projekten. Des Weiteren möchte ich mich bei allen Praktikanten und Masteranden bedanken: Konstantin Mallon, Niklas Böcher, Markus Hopf, David Voßiek, Sabrina Hampel und Fabian Huck. Sie alle haben wertvolle Beiträge zu meiner Arbeit geliefert. Von ganzem Herzen möchte ich mich bei meiner Familie bedanken. Ohne eure Unterstützung wäre ich nie soweit gekommen. Meiner Frau Johanna. Dir gilt mein größter Dank. Ich freue mich auf unser gemeinsames Leben. III Publications L. A. Huber, K. Hoffmann, S. Thumser, N. Böcher, P. Mayer, H. Dube*, Angew. Chem. 2017, 129, 14728-14731; Angew. Chem. Int. Ed. 2017, 56, 14536-14539. Direct Observation of Hemithioindigo- Motor Unidirectionality. Highlighted in Synfacts 2018, 14, 0080 and Laborpraxis 2017, 41, 34-35. L. A. Huber, P. Mayer, H. Dube*, ChemPhotoChem. 2018, 2, 458-464. Photoisomerization of Mono- Arylated Indigo and Water-Induced Acceleration of Thermal cis to trans Isomerization. (Front Cover) R. Wilcken+, M. Schildhauer+, F. Rott+, L. A. Huber, M. Guentner, S. Thumser, K. Hoffmann, S. Oesterling, R. de Vivie-Riedle, E. Riedle, H. Dube*, J. Am. Chem. Soc. 2018, 140, 5311-5318. Complete Mechanism of Hemithioindigo Motor Rotation. + contributed equally to the creation of the works IV Contributions [I] Niklas Böcher: Yield improvements and analytical data of 10, 17, 24. [II] Dr. Henry Dube: Identification of the signals of intermediates A-D of motor 5 (Figures 63 and 64). [III] Dr. Manuel Güntner: Investigations on motor 1 in collaboration with Monika Schildhauer, provided UV/vis spectra of motor 1. Condensation attempts of indanones 11 and 12 with benzothiophenone 6 and 9 (Figure 32, entries 1-12). [IV] Kerstin Hoffmann: Yield improvements and analytical data of 2 and 18. Crystallization of enantiomerically pure C-2, Structural confirmation of all enantiomers of motor 2 by chiral HPLC and crystal structure analysis. Experimental assessment of the energy profile of motor 2. [V] Fabian Huck: Elaboration of remote influences of bromine substituents on the thermal barriers of the helical inversions of HTI-based motors. [VI] Konstantin Mallon: Condensation attempt of indanone 12 with benzothiophenone 6 (Figure 32, entry 13). [VII] Dr. Peter Mayer: Measurement and identification of all structures in the crystalline states. [VIII] Monika Schildhauer: Experimentally determined energy profile of motor 1 in colloboration with Manuel Güntner, UV/vis spectra of motor 1. Synthesis of 10, 11. [IX] Stefan Thumser: Theoretical assessment of motors 1, 2 and 5, transition state structure of mixed indigo 88 and advice with regard to theoretical calculations. [X] David Voßiek: Crystallization of A-2 and C-3. Successful elaboration of the synthesis of motor 3 by applying the protocol of motor 2. Synthesis of 26. [XI] Dr. Sandra Wiedbrauk: Provided UV/vis spectra of HTI 14. [XII] Roland Wilcken: Transient absorption measurements of motors 1, 2 and 5. Quantum yield measurements and revelation of photonic limitations of HTI motors by rate modelling. V Abbreviations a annum Å angstrom (10-10 m) AIBN azobisisobutyronitrile a.u. arbitrary unit Boc tert-butoxycarbonyl c. concentrated °C °C cal calorie calc. calculated cis double bond configuration (indigo, historical nomenclature) cw clockwise ccw counterclockwise d doublet (experimental part, NMR analysis) d day(s) (Figure 31) δ chemical shifts, delta scale (in ppm) DADS decay associated difference spectrum DBPO dibenzoyl peroxide DCE 1,2-dichloroethane DIPEA N,N-diisopropylethylamine DME dimethoxyethane DMF N,N-dimethylformamide DMSO dimethyl sulfoxide E double bond configuration (entgegen) ε extinction coefficient [L·mol-1·cm-1] ECD electronic circular dichroism EI electronic ionization ESPT excited state proton transfer ESI electron spray ionization ESP electrostatic potential Et ethyl EtOAc ethyl acetate EtOH ethanol eV electron volt (1.6·10-16 J) FC Franck Condon (vertical excitation) Fmoc fluorenylmetoxycarbonyl VI FmocCl fluorenylmethoxycarbonyl chloride GSB ground state bleach h hour(s) HMBC heteronuclear multiple bond correlation HOMO highest occupied molecular orbital HPLC high performance liquid chromatography HR high resolution HSQC heteronucear quantum coherence HTI hemithioindigo Hz hertz [s-1] IC internal conversion iHex iso-hexane IR infrared (spectroscopy) ISC intersystem crossing J coupling constant (NMR) J joule K kelvin L liter LDA lithium diisopropylamide LOX lipoxygenase LUMO lowest unoccupied molecular orbital M helix configuration M molecular ion (mass spectrometry; experimental section) m meter m medium (IR) M multiplet (NMR analysis, experimental section) M molar Me methyl MEM 2-methoxyethoxymethyl MEMCl 2-methoxyethoxymethyl chloride min minute(s) m.p. melting point MS mass spectrometry m/z mass/charge ratio (MS; experimental section) 휈̃ wave number [cm-1] NBS N-bromosuccinimide nBuLi n-butyllithium VII NMR nuclear magnetic resonance NOESY nuclear Overhauser effect spectroscopy P helix configuration pss photostationary state q quartet R stereodescriptor Ra stereodescriptor (axial chirality) Rf retention factor S stereodescriptor Sa stereodescriptor (axial chirality) s strong (IR) s second(s) sep septet SET single electron transfer t triplet TBHP tert-butyl hydroperoxide TLC thin layer chromatography THF tetrahydrofuran TICT twisted intramolecular charge transfer TMEDA tetramethylethylenediamine trans double bond configuration (indigo, historical nomenclature) UV ultraviolet part of electromagnetic spectrum vis visible part of the electromagnetic spectrum vs very strong (IR) w weak (IR) Z double bond configuration (zusammen) VIII Table of Contents 1. Summary ......................................................................................................................................... 1 2. Zusammenfassung ........................................................................................................................... 4 3. Introduction: Light-matter interaction ............................................................................................. 9 3.1 Nature of light ......................................................................................................................... 9 3.2 Photon absorption .................................................................................................................. 10 3.3 Relaxation processes of molecules in the excited state ......................................................... 13 3.4 Photochemical reactions ........................................................................................................ 15 3.5 Photoswitches ........................................................................................................................ 19 3.5.1 Indigoid photoswitches .................................................................................................. 22 3.6 Molecular machinery ............................................................................................................
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