Reversible Switching Based on Truly Intramolecular Long-Range Proton Transfer─Turning the Theoretical Concept into Experimental Reality
Research output: Contribution to journal › Journal article › Research › peer-review
Herein, we demonstrate a working prototype of a conjugated proton crane, a reversible tautomeric switching molecule in which truly intramolecular long-range proton transfer occurs in solution at room temperature. The system consists of a benzothiazole rotor attached to a 7-hydroxy quinoline stator. According to the experimental and theoretical results, the OH proton is delivered under irradiation to the quinolyl nitrogen atom through a series of consecutive proton transfer and twisting steps. The use of a rigid rotor prevents undesired side processes that decrease the switching performance in previously described proton cranes and provides an unprecedented switching efficiency and fatigue resistance. The newly designed system confirms the theoretical concept for the application of proton transfer-initiated intramolecular twisting as the switching mechanism, developed more than 10 years ago, and provides unique insights for the further development of tautomeric molecular switches and motors, molecular logic gates, and new molecular-level energy storage systems.
| Original language | English |
|---|---|
| Journal | Journal of the American Chemical Society |
| Volume | 146 |
| Issue number | 3 |
| Pages (from-to) | 2043−2053 |
| Number of pages | 11 |
| ISSN | 0002-7863 |
| DOIs | |
| Publication status | Published - 2024 |
Bibliographical note
Funding Information:
Bulgarian National Science Fund (projects KP-06-DV-9/2019 and D01–168/2022); Alexander von Humboldt Foundation; German Science Foundation (projects 441234705, 404479188, and 437567992); Danish Council for Independent Research (DFF 4181–00206 and 9040–00265).
Funding Information:
Dedicated to Jakob (Joggi) Wirz (1942–2022), an inspiring mentor and generous colleague. The Bulgarian National Science Fund within the National Science Program VIHREN by project T-Motors (contracted as KP-06-DV-9/2019) is acknowledged for the financial support for this investigation. The authors acknowledge also the generous support from The Alexander von Humboldt Foundation (follow-up fellowship of L.A.) and the access provided to the e-infrastructure of the NCHDC ─part of the Bulgarian National Roadmap on RIs─with the financial support of Grant No. D01-168/28.07.2022. Furthermore, the authors are thankful to the German Science Foundation for financial support via the collaborative research center SFB 1477 “Light-Matter Interactions at Interfaces” (project number 441234705), the priority program SPP 2102 “Light Controlled Reactivity of Metal Complexes” (project number 404479188), and the international research training group IRTG 2676 “Imaging quantum systems: photons, molecules, materials” (project number 437567992). M.P. appreciates the support from the Danish Council for Independent Research (DFF 4181-00206 and 9040-00265) and from the University of Copenhagen.
Publisher Copyright:
© 2024 American Chemical Society.
ID: 381794208