A chiral self-sorting photoresponsive coordination cage based on overcrowded alkenes

Constantin Stuckhardt, Diederik Roke, Wojciech Danowski, Edwin Otten, Sander J. Wezenberg and Ben L. Feringa
Beilstein J. Org. Chem. 2019, 15, 2767–2773. https://doi.org/10.3762/bjoc.15.268

Supporting Information

Supporting Information File 1: Experimental procedures, compound characterization, CD spectroscopy, binding studies, NMR studies of the photochemical and thermal isomerizations, X-ray crystallography, computational details and Cartesian coordinates of DFT optimized structures.
Format: PDF Size: 3.7 MB Download

Cite the Following Article

A chiral self-sorting photoresponsive coordination cage based on overcrowded alkenes
Constantin Stuckhardt, Diederik Roke, Wojciech Danowski, Edwin Otten, Sander J. Wezenberg and Ben L. Feringa
Beilstein J. Org. Chem. 2019, 15, 2767–2773. https://doi.org/10.3762/bjoc.15.268

How to Cite

Stuckhardt, C.; Roke, D.; Danowski, W.; Otten, E.; Wezenberg, S. J.; Feringa, B. L. Beilstein J. Org. Chem. 2019, 15, 2767–2773. doi:10.3762/bjoc.15.268

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 850.8 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Walther, A.; Tusha, G.; Schmidt, B.; Holstein, J. J.; Schäfer, L. V.; Clever, G. H. Solvent-Directed Social Chiral Self-Sorting in Pd2L4 Coordination Cages. Journal of the American Chemical Society 2024. doi:10.1021/jacs.4c12525
  • Ovalle, M.; Stindt, C. N.; Feringa, B. L. Light, Switch, Action! The Influence of Geometrical Photoisomerization in an Adaptive Self-Assembled System. Journal of the American Chemical Society 2024, 146, 31892–31900. doi:10.1021/jacs.4c11206
  • Carbonell, A.; Izquierdo, I.; Guzmán Ríos, D. B.; Norjmaa, G.; Ujaque, G.; Martínez-Martínez, A. J.; Pischel, U. Synthesis, Characterization, and Photochemistry of a Ga2L3 Coordination Cage with Dithienylethene-Catecholate Ligands. Inorganic chemistry 2024, 63, 19872–19884. doi:10.1021/acs.inorgchem.4c03279
  • Ghorai, S.; Natarajan, R. Chiral Self-Sorting, Spontaneous Resolution, and Hierarchical Self-Assembly in Metal-Organic Cages. Small (Weinheim an der Bergstrasse, Germany) 2024, 20, e2400842. doi:10.1002/smll.202400842
  • Chen, D.; Chen, X.; Guo, Q.; Wang, J.; Wang, Q.; Zou, L. Effective guest uptake and release using an azobenzene-embedded molecular cage. Dyes and Pigments 2024, 222, 111795. doi:10.1016/j.dyepig.2023.111795
  • Benchimol, E.; Tessarolo, J.; Clever, G. H. Photoswitchable coordination cages. Nature chemistry 2024, 16, 13–21. doi:10.1038/s41557-023-01387-8
  • Zhu, J.; Sun, X.; Yang, X.; Yu, S.; Liang, L.; Chen, Y.; Zheng, X.; Yu, M.; Yan, L.; Tang, J.; Zhao, W.; Yang, X.; Wu, B. In Situ Photoisomerization of an Azobenzene‐Based Triple Helicate with a Prolonged Thermal Relaxation Time. Angewandte Chemie 2023, 135. doi:10.1002/ange.202314510
  • Zhu, J.; Sun, X.-W.; Yang, X.; Yu, S.-N.; Liang, L.; Chen, Y.-Z.; Zheng, X.; Yu, M.; Yan, L.; Tang, J.; Zhao, W.; Yang, X.-J.; Wu, B. In Situ Photoisomerization of an Azobenzene-Based Triple Helicate with a Prolonged Thermal Relaxation Time. Angewandte Chemie (International ed. in English) 2023, 62, e202314510. doi:10.1002/anie.202314510
  • Takimoto, K.; Shimada, T.; Nagura, K.; Hill, J. P.; Nakanishi, T.; Yuge, H.; Ishihara, S.; Labuta, J.; Sato, H. Thermo-/Mechano-Chromic Chiral Coordination Dimer: Formation of Switchable and Metastable Discrete Structure through Chiral Self-Sorting. Journal of the American Chemical Society 2023, 145, 25160–25169. doi:10.1021/jacs.3c05866
  • Nieland, E.; Voss, J.; Schmidt, B. M. Photoresponsive Supramolecular Cages and Macrocycles. ChemPlusChem 2023, 88, e202300353. doi:10.1002/cplu.202300353
  • Ludwig, C.; Xie, J. The Growing Field of Photoswitchable Macrocycles: A Promising Way to Tune Various Properties with Light. ChemPhotoChem 2023, 7. doi:10.1002/cptc.202300126
  • Zhu, J.; Chen, X.; Jin, X.; Wang, Q. Light-driven interconversion of Pd2L4 cage and mononuclear PdL2 mediated by the isomerization of azobenzene ligand. Chinese Chemical Letters 2023, 34, 108002. doi:10.1016/j.cclet.2022.108002
  • Shao, C.; Zhao, Y.; Han, S.; Huang, F.; Guo, W.; Jiang, H.; Wang, Y. Guest differentiation and fingerprinting based on the conformational diversity of a dynamic corannulene-based cage. Organic Chemistry Frontiers 2023, 10, 1412–1422. doi:10.1039/d2qo02028a
  • Ghorai, S.; Maji, S.; Paul, B.; Samanta, K.; Kumar Sen, S.; Natarajan, R. Chiral Self-Sorting in Pd6 L12 Metal-Organic Cages. Chemistry, an Asian journal 2023, 18, e202201312. doi:10.1002/asia.202201312
  • Lin, H.-Y.; Wang, Y.-T.; Shi, X.; Yang, H.-B.; Xu, L. Switchable metallacycles and metallacages. Chemical Society reviews 2023, 52, 1129–1154. doi:10.1039/d2cs00779g
  • Ghorai, S.; Natarajan, R. Anion-Driven Programmable Chiral Self-Sorting in Metal-Organic Cages and Structural Transformations between Heterochiral and Homochiral Cages. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 29, e202203085. doi:10.1002/chem.202203085
  • Hugenbusch, D.; Lehr, M.; von Glasenapp, J.; McConnell, A. J.; Herges, R. Lichtgesteuerte Konstruktion und Zerstörung: Schaltung zwischen zwei unterschiedlich zusammengesetzten käfigartigen Komplexen. Angewandte Chemie 2022, 135. doi:10.1002/ange.202212571
  • Hugenbusch, D.; Lehr, M.; von Glasenapp, J.-S.; McConnell, A. J.; Herges, R. Light-Controlled Destruction and Assembly: Switching between Two Differently Composed Cage-Type Complexes. Angewandte Chemie (International ed. in English) 2022, 62, e202212571. doi:10.1002/anie.202212571
  • Qin, Y.; Xiong, J.; Li, Q.; Zhang, Y.; Zeng, M.-H. Construction of Photo-Responsive Pd2 L4 -Type Nanocages based on Feringa's Second-Generation Motor and Its Guest Binding Ability for C60. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202201821. doi:10.1002/chem.202201821
  • DiNardi, R. G.; Douglas, A. O.; Tian, R.; Price, J. R.; Tajik, M.; Donald, W. A.; Beves, J. E. Visible-Light-Responsive Self-Assembled Complexes: Improved Photoswitching Properties by Metal Ion Coordination. Angewandte Chemie (International ed. in English) 2022, 61, e202205701. doi:10.1002/anie.202205701
Other Beilstein-Institut Open Science Activities