Hemithioindigo-based molecular machines for photocontrol of molecular transport, protein binding, and directional movement

• Applicant: Professor Dr. Henry Dube
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2014 to 2024
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 264598191

• Final Report Year: 2024

No abstract available

Publications

• Making Fast Photoswitches Faster—Using Hammett Analysis to Understand the Limit of Donor–Acceptor Approaches for Faster Hemithioindigo Photoswitches. Chemistry – A European Journal, 20(43), 13984-13992.
  Maerz, Benjamin; Wiedbrauk, Sandra; Oesterling, Sven; Samoylova, Elena; Nenov, Artur; Mayer, Peter; de Vivie‐Riedle, Regina; Zinth, Wolfgang & Dube, Henry
  
• Hemithioindigo—an emerging photoswitch. Tetrahedron Letters, 56(29), 4266-4274.
  Wiedbrauk, Sandra & Dube, Henry
  
• Sunlight-powered kHz rotation of a hemithioindigo-based molecular motor. Nature Communications, 6(1).
  Guentner, Manuel; Schildhauer, Monika; Thumser, Stefan; Mayer, Peter; Stephenson, David; Mayer, Peter J. & Dube, Henry
  
• Photocontrol of Polar Aromatic Interactions by a Bis‐Hemithioindigo Based Helical Receptor. Chemistry – A European Journal, 22(46), 16433-16436.
  Guentner, Manuel; Uhl, Edgar; Mayer, Peter & Dube, Henry
  
• Twisted Hemithioindigo Photoswitches: Solvent Polarity Determines the Type of Light-Induced Rotations. Journal of the American Chemical Society, 138(37), 12219-12227.
  Wiedbrauk, Sandra; Maerz, Benjamin; Samoylova, Elena; Reiner, Anne; Trommer, Florian; Mayer, Peter; Zinth, Wolfgang & Dube, Henry
  
• Bistable Photoswitching of Hemithioindigo with Green and Red Light: Entry Point to Advanced Molecular Digital Information Processing. Chemistry – A European Journal, 23(26), 6237-6243.
  Kink, Florian; Collado, Marina Polo; Wiedbrauk, Sandra; Mayer, Peter & Dube, Henry
  
• Direct Observation of Hemithioindigo‐Motor Unidirectionality. Angewandte Chemie International Edition, 56(46), 14536-14539.
  Huber, Ludwig Alexander; Hoffmann, Kerstin; Thumser, Stefan; Böcher, Niklas; Mayer, Peter & Dube, Henry
  
• Hemiindigo: Highly Bistable Photoswitching at the Biooptical Window. Journal of the American Chemical Society, 139(42), 15060-15067.
  Petermayer, Christian; Thumser, Stefan; Kink, Florian; Mayer, Peter & Dube, Henry
  
• Ingredients to TICT Formation in Donor Substituted Hemithioindigo. The Journal of Physical Chemistry Letters, 8(7), 1585-1592.
  Wiedbrauk, Sandra; Maerz, Benjamin; Samoylova, Elena; Mayer, Peter; Zinth, Wolfgang & Dube, Henry
  
• Synthesis of Double-Bond-Substituted Hemithioindigo Photoswitches. Organic Letters, 20(1), 232-235.
  Gerwien, Aaron; Reinhardt, Till; Mayer, Peter & Dube, Henry
  
• 2‐(4′‐Pyridyl‐N‐oxide)‐Substituted Hemithioindigos as Photoresponsive Guests for a Super Aryl‐Extended Calix[4]pyrrole Receptor. Chemistry – An Asian Journal, 13(12), 1632-1639.
  Moncelsi, Giulia; Escobar, Luis; Dube, Henry & Ballester, Pablo
  
• Circular Dichroism Photoswitching with a Twist: Axially Chiral Hemiindigo. Journal of the American Chemical Society, 140(42), 13558-13561.
  Petermayer, Christian & Dube, Henry
  
• Complete Mechanism of Hemithioindigo Motor Rotation. Journal of the American Chemical Society, 140(15), 5311-5318.
  Wilcken, Roland; Schildhauer, Monika; Rott, Florian; Huber, Ludwig Alexander; Guentner, Manuel; Thumser, Stefan; Hoffmann, Kerstin; Oesterling, Sven; de Vivie-Riedle, Regina; Riedle, Eberhard & Dube, Henry
  
• Direct evidence for hula twist and single-bond rotation photoproducts. Nature Communications, 9(1).
  Gerwien, Aaron; Schildhauer, Monika; Thumser, Stefan; Mayer, Peter & Dube, Henry
  
• Indigoid Photoswitches: Visible Light Responsive Molecular Tools. Accounts of Chemical Research, 51(5), 1153-1163.
  Petermayer, Christian & Dube, Henry
  
• Photoisomerization of Mono‐Arylated Indigo and Water‐Induced Acceleration of Thermal cis‐to‐trans Isomerization. ChemPhotoChem, 2(6), 458-464.
  Huber, Ludwig A.; Mayer, Peter & Dube, Henry
  
• Photon-Only Molecular Motor with Reverse Temperature-Dependent Efficiency. Journal of the American Chemical Society, 140(48), 16442-16445.
  Gerwien, Aaron; Mayer, Peter & Dube, Henry
  
• Simultaneous complementary photoswitching of hemithioindigo tweezers for dynamic guest relocalization. Nature Communications, 9(1).
  Wiedbrauk, Sandra; Bartelmann, Thomas; Thumser, Stefan; Mayer, Peter & Dube, Henry
  
• Transforming hemithioindigo from a two-way to a one-way molecular photoswitch by isolation in the gas phase. Physical Chemistry Chemical Physics, 20(10), 6868-6876.
  Navrátil, Rafael; Wiedbrauk, Sandra; Jašík, Juraj; Dube, Henry & Roithová, Jana
  
• Transmission of Unidirectional Molecular Motor Rotation to a Remote Biaryl Axis. Angewandte Chemie International Edition, 57(34), 11064-11068.
  Uhl, Edgar; Thumser, Stefan; Mayer, Peter & Dube, Henry
  
• A hemithioindigo molecular motor for metal surface attachment. Organic & Biomolecular Chemistry, 17(7), 1979-1983.
  Hoffmann, Kerstin; Mayer, Peter & Dube, Henry
  
• A Prospective Ultrafast Hemithioindigo Molecular Motor. ChemPhotoChem, 3(6), 365-371.
  Schildhauer, Monika; Rott, Florian; Thumser, Stefan; Mayer, Peter; de Vivie‐Riedle, Regina & Dube, Henry
  
• Green light powered molecular state motor enabling eight-shaped unidirectional rotation. Nature Communications, 10(1).
  Gerwien, Aaron; Mayer, Peter & Dube, Henry
  
• Symmetric and nonsymmetric bis-hemithioindigos – precise visible light controlled shape-shifters. Organic Chemistry Frontiers, 6(8), 1244-1252.
  Hoffmann, Kerstin; Guentner, Manuel; Mayer, Peter & Dube, Henry
  
• Active and Unidirectional Acceleration of Biaryl Rotation by a Molecular Motor. Angewandte Chemie International Edition, 59(14), 5730-5737.
  Uhl, Edgar; Mayer, Peter & Dube, Henry
  
• Light‐Controlled Cell‐Cycle Arrest and Apoptosis. Angewandte Chemie International Edition, 60(3), 1187-1196.
  Uhl, Edgar; Wolff, Friederike; Mangal, Sriyash; Dube, Henry & Zanin, Esther
  
• Oxidized Hemithioindigo Photoswitches—Influence of Oxidation State on (Photo)physical and Photochemical Properties. Chemistry – A European Journal, 26(47), 10712-10718.
  Köttner, Laura; Schildhauer, Monika; Wiedbrauk, Sandra; Mayer, Peter & Dube, Henry
  
• Proton-conduction photomodulation in spiropyran-functionalized MOFs with large on–off ratio. Chemical Science, 11(5), 1404-1410.
  Kanj, Anemar Bruno; Chandresh, Abhinav; Gerwien, Aaron; Grosjean, Sylvain; Bräse, Stefan; Wang, Yuemin; Dube, Henry & Heinke, Lars
  
• Reversible Photoswitching of Isolated Ionic Hemiindigos with Visible Light. ChemPhysChem, 21(7), 680-685.
  Carrascosa, Eduardo; Petermayer, Christian; Scholz, Michael S.; Bull, James N.; Dube, Henry & Bieske, Evan J.
  
• Supramolecular Relay-Control of Organocatalysis with a Hemithioindigo-Based Molecular Motor. Journal of the American Chemical Society, 142(45), 19300-19307.
  Grill, Kerstin & Dube, Henry
  
• Tuning the Ground and Excited State Dynamics of Hemithioindigo Molecular Motors by Changing Substituents. Chemistry – A European Journal, 26(59), 13507-13512.
  Wilcken, Roland; Huber, Ludwig; Grill, Kerstin; Guentner, Manuel; Schildhauer, Monika; Thumser, Stefan; Riedle, Eberhard & Dube, Henry
  
• All-Red-Light Photoswitching of Indirubin Controlled by Supramolecular Interactions. Journal of the American Chemical Society, 143(43), 18251-18260.
  Thumser, Stefan; Köttner, Laura; Hoffmann, Nadine; Mayer, Peter & Dube, Henry
  
• Electronic and Geometric Characterization of TICT Formation in Hemithioindigo Photoswitches by Picosecond Infrared Spectroscopy. The Journal of Physical Chemistry A, 125(20), 4390-4400.
  Stallhofer, Klara; Nuber, Matthias; Schüppel, Franziska; Thumser, Stefan; Iglev, Hristo; de Vivie-Riedle, Regina; Zinth, Wolfgang & Dube, Henry
  
• Steric Effects on the Thermal Processes of Hemithioindigo Based Molecular Motor Rotation. Chemistry – A European Journal, 27(41), 10758-10765.
  Huber, Ludwig A.; Thumser, Stefan; Grill, Kerstin; Voßiek, David; Bach, Nicolai N.; Mayer, Peter & Dube, Henry
  
• Sulfoxide hemithioindigo tweezers – visible light addressable capture and release. Chemical Science, 12(10), 3651-3659.
  Bartelmann, Thomas; Gnannt, Frederik; Zitzmann, Max; Mayer, Peter & Dube, Henry
  
• Active Mechanical Threading by a Molecular Motor**. Angewandte Chemie International Edition, 61(19).
  Bach, Nicolai N.; Josef, Verena; Maid, Harald & Dube, Henry
  
• An Eight-State Molecular Sequential Switch Featuring a Dual Single-Bond Rotation Photoreaction. Journal of the American Chemical Society, 144(7), 3029-3038.
  Gerwien, Aaron; Jehle, Benjamin; Irmler, Marvin; Mayer, Peter & Dube, Henry
  
• Hemithioindigo-Based Trioxobicyclononadiene: 3D Multiswitching of Electronic and Geometric Properties. Journal of the American Chemical Society, 144(7), 2847-2852.
  Kohl, Fabien; Gerwien, Aaron; Hampel, Frank; Mayer, Peter & Dube, Henry
  
• Heterocyclic Hemithioindigos: Highly Advantageous Properties as Molecular Photoswitches**. Angewandte Chemie International Edition, 61(43).
  Josef, Verena; Hampel, Frank & Dube, Henry
  
• Indigoid Photoswitches. Molecular Photoswitches, 283-302. Wiley.
  Bartelmann, Thomas & Dube, Henry
  
• Photogearing as a concept for translation of precise motions at the nanoscale. Nature Chemistry, 14(6), 670-676.
  Gerwien, Aaron; Gnannt, Frederik; Mayer, Peter & Dube, Henry
  
• Quantitative In‐Situ NMR Illumination for Excitation and Kinetic Analysis of Molecular Motor Intermediates. ChemPhotoChem, 6(2).
  Wilcken, Roland; Gerwien, Aaron; Huber, Ludwig Alexander; Dube, Henry & Riedle, Eberhard
  
• A cross-conjugation approach for high-performance diaryl-hemithioindigo photoswitches. Chemical Science, 14(21), 5734-5742.
  Zitzmann, Max; Hampel, Frank & Dube, Henry
  
• A photochemical method to evidence directional molecular motions. Nature Communications, 14(1).
  Regen-Pregizer, Benjamin Lukas; Ozcelik, Ani; Mayer, Peter; Hampel, Frank & Dube, Henry
  
• Azotriptycenes: Photoswitchable Molecular Brakes. Chemistry – A European Journal, 30(6).
  Stockerl, Willibald J.; Reißenweber, Lilli; Gerwien, Aaron; Bach, Nicolai N.; Thumser, Stefan; Mayer, Peter; Gschwind, Ruth M. & Dube, Henry
  
• Defining Unidirectional Motions and Structural Reconfiguration in a Macrocyclic Molecular Motor. Journal of the American Chemical Society, 145(24), 13081-13088.
  Regen-Pregizer, Benjamin Lukas & Dube, Henry
  
• Diaryl-hemiindigos as visible light, pH, and heat responsive four-state switches and application in photochromic transparent polymers. Nature Communications, 14(1).
  Sacherer, Maximilian; Hampel, Frank & Dube, Henry
  
• Mechanistic Elucidation of the Hula-Twist Photoreaction in Hemithioindigo. Journal of the American Chemical Society, 145(27), 14811-14822.
  Fischer, Tobias; Leitner, Jonas; Gerwien, Aaron; Mayer, Peter; Dreuw, Andreas; Dube, Henry & Wachtveitl, Josef
  
• Peri‐Anthracenethioindigo: A Scaffold for Efficient All‐Red‐Light and Near‐Infrared Molecular Photoswitching**. Angewandte Chemie International Edition, 62(52).
  Köttner, Laura; Ciekalski, Elias & Dube, Henry
  
• A Supercharged Molecular Motor Operating by Constitutional Alteration and Hydrogen Bonding.
  Dube, Henry; Biswas, Pronay; Ozcelik, Ani; Hartinger, Martina & Hampel, Frank
  
• Directional Bias in Molecular Photogearing Evidenced by LED‐Coupled Chiral Cryo‐HPLC. Angewandte Chemie, 136(38).
  Gnannt, Frederik; Gerwien, Aaron; Waldmannstetter, Sven; Gracheva, Sofia & Dube, Henry
  
• Directionality Reversal and Shift of Rotational Axis in a Hemithioindigo Macrocyclic Molecular Motor. Journal of the American Chemical Society, 146(33), 23387-23397.
  Reißenweber, Lilli; Uhl, Edgar; Hampel, Frank; Mayer, Peter & Dube, Henry
  
• Gain of Function Recyclable Photoswitches: Reversible Simultaneous Substitution and Photochromism Generation. Angewandte Chemie International Edition, 63(21).
  Zitzmann, Max; Fröhling, Matthias & Dube, Henry
  
• Path‐Independent All‐Visible Orthogonal Photoswitching for Applications in Multi‐Photochromic Polymers and Molecular Computing. Angewandte Chemie International Edition, 63(44).
  Köttner, Laura & Dube, Henry
  
• Reversible C═N Bond Formation Controls Charge-Separation in an Aza-Diarylethene Photoswitch. Journal of the American Chemical Society, 146(14), 9575-9582.
  Sacherer, Maximilian; Gracheva, Sofia; Maid, Harald; Placht, Christian; Hampel, Frank & Dube, Henry
  
• Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis. Journal of the American Chemical Society, 146(3), 1894-1903.
  Köttner, Laura; Wolff, Friederike; Mayer, Peter; Zanin, Esther & Dube, Henry