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Photochemical and Thermal Isomerization of a Ruthenium(II)−Alloxazine Complex Involving an Unusual Coordination Mode

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Department of Material and Life Science, Graduate School of Engineering, Osaka University, SORST, Japan Science and Technology Agency (JST), Suita, Osaka 565-0871, Japan
Cite this: J. Am. Chem. Soc. 2008, 130, 5, 1556–1557
Publication Date (Web):January 12, 2008
https://doi.org/10.1021/ja077954a
Copyright © 2008 American Chemical Society
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Abstract

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A Ru(II) complex having a flavin analogue as a ligand in a unusual coordination mode exhibits a photochemical and thermal isomerization; the bistability of the complex is attained by chelate effect and intramolecular CH···O interaction.

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Experimental details, an Eyring plot, time profiles of the transient absorptions, ESI-MS and 1H NMR spectra of the intermediate (I). This material is available free of charge via the Internet at http://pubs.acs.org.

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This article is cited by 35 publications.

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  2. Masanari Hirahara, Sho Nagai, Kosuke Takahashi, Kenji Saito, Tatsuto Yui, and Masayuki Yagi . New Series of Dinuclear Ruthenium(II) Complexes Synthesized Using Photoisomerization for Efficient Water Oxidation Catalysis. Inorganic Chemistry 2015, 54 (15) , 7627-7635. https://doi.org/10.1021/acs.inorgchem.5b01264
  3. Fritz Weisser, Sebastian Plebst, Stephan Hohloch, Margarethe van der Meer, Sinja Manck, Felix Führer, Vanessa Radtke, Daniel Leichnitz, and Biprajit Sarkar . Tuning Ligand Effects and Probing the Inner-Workings of Bond Activation Steps: Generation of Ruthenium Complexes with Tailor-Made Properties. Inorganic Chemistry 2015, 54 (10) , 4621-4635. https://doi.org/10.1021/ic502807d
  4. Prasenjit Mondal, Ritwika Ray, Ankita Das, and Goutam Kumar Lahiri . Revelation of Varying Bonding Motif of Alloxazine, a Flavin Analogue, in Selected Ruthenium(II/III) Frameworks. Inorganic Chemistry 2015, 54 (6) , 3012-3021. https://doi.org/10.1021/acs.inorgchem.5b00122
  5. Lina Ding, Lung Wa Chung, and Keiji Morokuma . Excited-State Proton Transfer Controls Irreversibility of Photoisomerization in Mononuclear Ruthenium(II) Monoaquo Complexes: A DFT Study. Journal of Chemical Theory and Computation 2014, 10 (2) , 668-675. https://doi.org/10.1021/ct400982r
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  11. Masanari Hirahara, Akira Tsukamoto, Hiroki Goto, Shigeru Tada, Masayuki Yagi, Yasushi Umemura. Visible-Light-Induced Morphological Changes of Giant Vesicles by Photoisomerization of a Ruthenium Aqua Complex. Chemistry - A European Journal 2016, 22 (8) , 2590-2594. https://doi.org/10.1002/chem.201504249
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  14. Sei’ichi Tanaka, Kosuke Takahashi, Masanari Hirahara, Masayuki Yagi, Ken Onda. Characterization of the excited states of distal- and proximal-[Ru(tpy)(pynp)OH2]2+ in aqueous solution using time-resolved infrared spectroscopy. Journal of Photochemistry and Photobiology A: Chemistry 2015, 313 , 87-98. https://doi.org/10.1016/j.jphotochem.2015.06.018
  15. Yicheng Zhang, Jianteng Wang, Xiaodong Tao, Li Song, Wenxiang Chai. A Supramolecular Framework Structure of a Novel Heterometallic Sn–Zn Dinuclear Cluster Constructed by a Sulfur-Contained Complex Unit. Phosphorus, Sulfur, and Silicon and the Related Elements 2015, 190 (9) , 1434-1442. https://doi.org/10.1080/10426507.2014.986270
  16. Masanari Hirahara, Tomoya Hakamata, Aaron B. League, Mehmed Z. Ertem, Kosuke Takahashi, Sho Nagai, Keisuke Inaba, Hirosato Yamazaki, Kenji Saito, Tatsuto Yui, Christopher J. Cramer, Masayuki Yagi. Mechanisms and Factors Controlling Photoisomerization Equilibria, Ligand Exchange, and Water Oxidation Catalysis Capabilities of Mononuclear Ruthen­ium(II) Complexes. European Journal of Inorganic Chemistry 2015, 2015 (23) , 3892-3903. https://doi.org/10.1002/ejic.201500642
  17. Francis D'Souza, Hiroshi Imahori. Preface — Special Issue in Honor of Professor Shunichi Fukuzumi. Journal of Porphyrins and Phthalocyanines 2015, 19 (01-03) , i-xvi. https://doi.org/10.1142/S1088424615020010
  18. Franz Müller. NMR Spectroscopy on Flavins and Flavoproteins. 2014,,, 229-306. https://doi.org/10.1007/978-1-4939-0452-5_11
  19. , . Flavins and Flavoproteins. 2014,,https://doi.org/10.1007/978-1-4939-0452-5
  20. Takuya Sawaki, Tomoya Ishizuka, Masaki Kawano, Yoshihito Shiota, Kazunari Yoshizawa, Takahiko Kojima. Complete Photochromic Structural Changes in Ruthenium(II)Diimine Complexes, Based on Control of the Excited States by Metalation. Chemistry - A European Journal 2013, 19 (27) , 8978-8990. https://doi.org/10.1002/chem.201300437
  21. Chunrui Wu, Pan Li, Yuesi Fang, Jingjing Zhao, Weichao Xue, Yang Li, Richard C. Larock, Feng Shi. Pd-catalyzed oxidative coupling of monosubstituted sydnones and terminal alkynes. Tetrahedron Letters 2011, 52 (29) , 3797-3801. https://doi.org/10.1016/j.tetlet.2011.05.058
  22. Tomoya Ishizuka, Takuya Sawaki, Soushi Miyazaki, Masaki Kawano, Yoshihito Shiota, Kazunari Yoshizawa, Shunichi Fukuzumi, Takahiko Kojima. Mechanistic Insights into Photochromic Behavior of a Ruthenium(II)-Pterin Complex. Chemistry - A European Journal 2011, 17 (24) , 6652-6662. https://doi.org/10.1002/chem.201003522
  23. Atsushi Kobayashi, Korin Ohbayashi, Rie Aoki, Ho-Chol Chang, Masako Kato. Synthesis, structure and photophysical properties of a flavin-based platinum(ii) complex. Dalton Transactions 2011, 40 (14) , 3484. https://doi.org/10.1039/c0dt01139h
  24. Yosuke Kanai, Varadharajan Srinivasan, Steven K. Meier, K. Peter C. Vollhardt, Jeffrey C. Grossman. Mechanism of Thermal Reversal of the (Fulvalene)tetracarbonyldiruthenium Photoisomerization: Toward Molecular Solar-Thermal Energy Storage. Angewandte Chemie 2010, 122 (47) , 9110-9113. https://doi.org/10.1002/ange.201002994
  25. Yosuke Kanai, Varadharajan Srinivasan, Steven K. Meier, K. Peter C. Vollhardt, Jeffrey C. Grossman. Mechanism of Thermal Reversal of the (Fulvalene)tetracarbonyldiruthenium Photoisomerization: Toward Molecular Solar-Thermal Energy Storage. Angewandte Chemie International Edition 2010, 49 (47) , 8926-8929. https://doi.org/10.1002/anie.201002994
  26. Johannes G. Vos, Mary T. Pryce. Photoinduced rearrangements in transition metal compounds. Coordination Chemistry Reviews 2010, 254 (21-22) , 2519-2532. https://doi.org/10.1016/j.ccr.2010.04.010
  27. Ming-Sheng Wang, Gang Xu, Zhang-Jing Zhang, Guo-Cong Guo. Inorganic–organic hybrid photochromic materials. Chem. Commun. 2010, 46 (3) , 361-376. https://doi.org/10.1039/B917890B
  28. Wenxiang Chai, Li Song, Hangyan Shen, Kangying Shu. Synthesis, Crystal Structure, and Luminescence of a Three-Dimensional Supramolecular Compound Based on a Dinuclear Tin Cluster. Phosphorus, Sulfur, and Silicon and the Related Elements 2009, 184 (12) , 3212-3220. https://doi.org/10.1080/10426500902839400
  29. Magdalena Bruszyńska, Ewa Sikorska, Anna Komasa, Igor Khmelinskii, Luis F.V. Ferreira, Jordi Hernando, Jerzy Karolczak, Maciej Kubicki, Jose L. Bourdelande, Marek Sikorski. Electronic structure and spectral properties of selected trimethyl-alloxazines: Combined experimental and DFT study. Chemical Physics 2009, 361 (1-2) , 83-93. https://doi.org/10.1016/j.chemphys.2009.05.011
  30. Nathan J. Patmore. Photophysical properties of metal complexes. Annual Reports Section "A" (Inorganic Chemistry) 2009, 105 , 525. https://doi.org/10.1039/b818289m
  31. Paul T. Maragh. Reaction mechanisms in solution. Annual Reports Section "A" (Inorganic Chemistry) 2009, 105 , 416. https://doi.org/10.1039/b818297n
  32. Takahiko Kojima, Yuji Inui, Soushi Miyazaki, Motoo Shiro, Shunichi Fukuzumi. A tetranuclear iridium(iii) complex with a flavin analogue as a bridging ligand in different coordination modes and exchangeable anion encapsulation in a supramolecular cage. Chemical Communications 2009, 43 (43) , 6643. https://doi.org/10.1039/b911033j
  33. Takahiko Kojima, Tsuyoshi Morimoto, Taisuke Sakamoto, Soushi Miyazaki, Shunichi Fukuzumi. Ruthenium(II) Pyridylamine Complexes with Diimine Ligands Showing Reversible Photochemical and Thermal Structural Change. Chemistry - A European Journal 2008, 14 (29) , 8904-8915. https://doi.org/10.1002/chem.200800827
  34. Shoko Kume, Hiroshi Nishihara. Photochrome-coupled metal complexes: molecular processing of photon stimuli. Dalton Transactions 2008, 100 (25) , 3260. https://doi.org/10.1039/b716947g
  35. Takahiko Kojima. A Chemistry of Ruthenium-Tris(2-pyridylmethyl)amine Complexes. Bulletin of Japan Society of Coordination Chemistry 2008, 52 (0) , 3-16. https://doi.org/10.4019/bjscc.52.3

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