Reversible switching of arylazopyrazole within a metal–organic cage

Anton I. Hanopolskyi, Soumen De, Michał J. Białek, Yael Diskin-Posner, Liat Avram, Moran Feller and Rafal Klajn
Beilstein J. Org. Chem. 2019, 15, 2398–2407. https://doi.org/10.3762/bjoc.15.232

Supporting Information

The Supporting Information features further experimental details, including synthesis and characterization of arylazopyrazole 1, characterization of inclusion complexes (E-1)2[Graphic 2]2 and (Z-1)[Graphic 2]2, photoisomerization and thermal relaxation studies, and details on X-ray data collection and refinement. In addition, X-ray data for inclusion complex (E-1)2[Graphic 2]2 and the energy-optimized structure for inclusion complex (Z-1)[Graphic 2]2 are given.

Supporting Information File 1: Further experimental details.
Format: PDF Size: 9.1 MB Download
Supporting Information File 2: X-ray data for inclusion complex (E-1)2[Graphic 2]2.
Format: CIF Size: 6.3 MB Download
Supporting Information File 3: Energy-optimized structure for inclusion complex (Z-1)[Graphic 2]2.
Format: MOL2 Size: 20.6 KB Download

Cite the Following Article

Reversible switching of arylazopyrazole within a metal–organic cage
Anton I. Hanopolskyi, Soumen De, Michał J. Białek, Yael Diskin-Posner, Liat Avram, Moran Feller and Rafal Klajn
Beilstein J. Org. Chem. 2019, 15, 2398–2407. https://doi.org/10.3762/bjoc.15.232

How to Cite

Hanopolskyi, A. I.; De, S.; Białek, M. J.; Diskin-Posner, Y.; Avram, L.; Feller, M.; Klajn, R. Beilstein J. Org. Chem. 2019, 15, 2398–2407. doi:10.3762/bjoc.15.232

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: 427.7 KB Download

Citations to This Article

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

Scholarly Works

  • Hema, K.; Grommet, A. B.; Białek, M. J.; Wang, J.; Schneider, L.; Drechsler, C.; Yanshyna, O.; Diskin-Posner, Y.; Clever, G. H.; Klajn, R. Guest Encapsulation Alters the Thermodynamic Landscape of a Coordination Host. Journal of the American Chemical Society 2023. doi:10.1021/jacs.3c08666
  • Gemen, J.; Church, J. R.; Ruoko, T.-P.; Durandin, N.; Białek, M. J.; Weißenfels, M.; Feller, M.; Kazes, M.; Odaybat, M.; Borin, V. A.; Kalepu, R.; Diskin-Posner, Y.; Oron, D.; Fuchter, M. J.; Priimagi, A.; Schapiro, I.; Klajn, R. Disequilibrating azobenzenes by visible-light sensitization under confinement. Science (New York, N.Y.) 2023, 381, 1357–1363. doi:10.1126/science.adh9059
  • Strugach, D. S.; Hadar, D.; Amiram, M. Robust Photocontrol of Elastin-like Polypeptide Phase Transition with a Genetically Encoded Arylazopyrazole. ACS synthetic biology 2023, 12, 2802–2811. doi:10.1021/acssynbio.3c00146
  • Gupta, D.; Gaur, A. K.; Kumar, H.; Singh, S.; Venkataramani, S. Light‐Switchable Metal Complexes: Introducing Photoresponsive Behaviour Through Azoheteroarenes. ChemPhotoChem 2023, 7. doi:10.1002/cptc.202300068
  • Wang, S.-T.; Tan, P.; Weng, W.-Q.; Zheng, L.; Liu, X.-Q.; Sun, L.-B. Photoresponsive metal-organic polyhedra in metal-organic frameworks: Achieving "real" responsiveness. Science China Materials 2023, 66, 2726–2732. doi:10.1007/s40843-022-2428-7
  • Mandal, P.; Pratihar, J. L. A review of the photochromic behavior of metal complexes embedded in conjugated (–N=N–C=N–) and non-conjugated azo-imine-based ligands. Reviews in Inorganic Chemistry 2023, 43, 583–625. doi:10.1515/revic-2022-0039
  • Rybak, C. J.; Andjaba, J. M.; Fan, C.; Zeller, M.; Uyeda, C. Dinickel-Catalyzed N═N Bond Rotation. Inorganic chemistry 2023, 62, 5886–5891. doi:10.1021/acs.inorgchem.3c00415
  • Arndt, N. B.; Adolphs, T.; Arlinghaus, H. F.; Heidrich, B.; Ravoo, B. J. Arylazopyrazole-Modified Thiolactone Acrylate Copolymer Brushes for Tuneable and Photoresponsive Wettability of Glass Surfaces. Langmuir : the ACS journal of surfaces and colloids 2023, 39, 5342–5351. doi:10.1021/acs.langmuir.2c03400
  • Li, X.; Qian, K.; Huang, L. Emerging Biosensors Based on Noble Metal Self‐Assembly for In Vitro Disease Diagnosis. Advanced NanoBiomed Research 2023, 3. doi:10.1002/anbr.202200148
  • Samanta, S. K. Metal Organic Polygons and Polyhedra: Instabilities and Remedies. Inorganics 2023, 11, 36. doi:10.3390/inorganics11010036
  • Han, X.; Ding, L.; Hao, X.-Q.; Guo, Y.; Shi, L. A Water-Soluble Supermolecular Cage for Artificial Light-Harvesting Nanoreactors. Elsevier BV 2023. doi:10.2139/ssrn.4606165
  • Thaggard, G. C.; Haimerl, J.; Park, K. C.; Lim, J.; Fischer, R. A.; Maldeni Kankanamalage, B. K. P.; Yarbrough, B. J.; Wilson, G. R.; Shustova, N. B. Metal-Photoswitch Friendship: From Photochromic Complexes to Functional Materials. Journal of the American Chemical Society 2022, 144, 23249–23263. doi:10.1021/jacs.2c09879
  • Wang, J.; Avram, L.; Diskin-Posner, Y.; Białek, M. J.; Stawski, W.; Feller, M.; Klajn, R. Altering the Properties of Spiropyran Switches Using Coordination Cages with Different Symmetries. Journal of the American Chemical Society 2022, 144, 21244–21254. doi:10.1021/jacs.2c08901
  • Gemen, J.; Białek, M. J.; Kazes, M.; Shimon, L. J. W.; Feller, M.; Semenov, S. N.; Diskin-Posner, Y.; Oron, D.; Klajn, R. Ternary host-guest complexes with rapid exchange kinetics and photoswitchable fluorescence. Chem 2022, 8, 2362–2379. doi:10.1016/j.chempr.2022.05.008
  • Santamaria-Garcia, V. J.; Flores-Hernandez, D. R.; Contreras-Torres, F. F.; Cué-Sampedro, R.; Sánchez-Fernández, J. A. Advances in the Structural Strategies of the Self-Assembly of Photoresponsive Supramolecular Systems. International journal of molecular sciences 2022, 23, 7998. doi:10.3390/ijms23147998
  • Greenfield, J. L.; Thawani, A. R.; Odaybat, M.; Gibson, R. S.; Jackson, T. B.; Fuchter, M. J. doi:10.1002/9783527827626.ch5
  • Le, M.; Han, G. G. D. Stimuli-Responsive Organic Phase Change Materials: Molecular Designs and Applications in Energy Storage. Accounts of Materials Research 2022, 3, 634–643. doi:10.1021/accountsmr.2c00049
  • Gupta, D.; Gaur, A. K.; Chauhan, D.; Thakur, S. K.; Jeyapalan, V.; Singh, S.; Rajaraman, G.; Venkataramani, S. Solid-state photochromic arylazopyrazole-based transition metal complexes. Inorganic Chemistry Frontiers 2022, 9, 2315–2327. doi:10.1039/d2qi00325b
  • Yanshyna, O.; Białek, M. J.; Chashchikhin, O. V.; Klajn, R. Encapsulation within a coordination cage modulates the reactivity of redox-active dyes. Communications chemistry 2022, 5, 44. doi:10.1038/s42004-022-00658-8
  • Leistner, A.; Pianowski, Z. L. Smart Photochromic Materials Triggered with Visible Light. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202101271
Other Beilstein-Institut Open Science Activities