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Pure Appl. Chem., 2004, Vol. 76, No. 2, pp. 277-293

http://dx.doi.org/10.1351/pac200476020277

Recent developments in the coordination chemistry of stable free radicals*

M. T. Lemaire

Department of Chemistry, Memorial University of Newfoundland, St. John’s, NL A1B 3X7, Canada

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  • Qiao Xue-Mei, Zhang Chen-Xi, Kong Yu-Kun, Wang Qing-Lun, Zhang Yu-Ying: Two Mononuclear Tri-Spin Compounds based on the Lanthanide-Nitronyl Nitroxide Radicals: Synthesis, Crystal Structure, and Magnetic Properties. Z. anorg. allg. Chem. 2014, n/a. <http://dx.doi.org/10.1002/zaac.201300655>
  • Wang Ya-Li, Gao Yuan-Yuan, Ma Yue, Wang Qing-Lun, Li Li-Cun, Liao Dai-Zheng: Syntheses, crystal structures, magnetic and luminescence properties of five novel lanthanide complexes of nitronyl nitroxide radical. Journal of Solid State Chemistry 2013, 202, 276. <http://dx.doi.org/10.1016/j.jssc.2013.03.052>
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  • Kasumov Veli T., Yerli Yusuf, Topkaya Ramazan: Magnetic properties of a new N-TEMPO-tert-butyl substituted salicylaldimines and their biradical palladium(II) complexes. Solid State Sciences 2013, 15, 95. <http://dx.doi.org/10.1016/j.solidstatesciences.2012.10.003>
  • Pang Xue, Zhao Xiao Ran, Wang Hui, Sun Hao-Ling, Jin Wei Jun: Modulating Crystal Packing and Magnetic Properties of Nitroxide Free Radicals by Halogen Bonding. Crystal Growth & Design 2013, 13, 3739. <http://dx.doi.org/10.1021/cg400776x>
  • Bogart Justin A., Lee Heui Beom, Boreen Michael A., Jun Minsik, Schelter Eric J.: Fine-Tuning the Oxidative Ability of Persistent Radicals: Electrochemical and Computational Studies of Substituted 2-Pyridylhydroxylamines. J. Org. Chem. 2013, 78, 6344. <http://dx.doi.org/10.1021/jo400944r>
  • Shuvaev Konstantin V., Sproules Stephen, Rautiainen J. Mikko., McInnes Eric J. L., Collison David, Anson Christopher E., Powell Annie K.: A self-assembled Cu(ii)4 [2 × 2] grid with organic radicals. Dalton Trans. 2013, 42, 2371. <http://dx.doi.org/10.1039/c2dt31946b>
  • Cheng Wei-Qin, Zhang Li-Fang, Ni Zhong-Hai, Kou Hui-Zhong: Synthesis, Crystal Structure, and Magnetic Properties of a Mn(III)-radical Complex. Bulletin of the Korean Chemical Society 2013, 34, 2195. <http://dx.doi.org/10.5012/bkcs.2013.34.7.2195>
  • Datcu Angela, Roques Nans, Jubera Véronique, Maspoch Daniel, Fontrodona Xavier, Wurst Klaus, Imaz Inhar, Mouchaham Georges, Sutter Jean-Pascal, Rovira Concepció: Three-Dimensional Porous Metal-Radical Frameworks Based on Triphenylmethyl Radicals. Chemistry A European Journal 2012, 18, 152. <http://dx.doi.org/10.1002/chem.201102278>
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  • Yong Guo-Ping, Li Ying-Zhou, Zhang Yi-Man, She Wen-Long: Magnetic and luminescent properties of Cd(ii)- and Fe(ii)-anion radical frameworks: various networks or structures influenced by metal ion sizes or in situ forming mechanisms of anion radical ligand. CrysEngComm 2012, 14, 1439. <http://dx.doi.org/10.1039/c1ce05641g>
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  • Wang Ya-Li, Gao Yuan-Yuan, Ma Yue, Wang Qing-Lun, Li Li-Cun, Liao Dai-Zheng: A family of lanthanide–nitronyl nitroxide complexes: syntheses, crystal structures and magnetic properties. CrystEngComm 2012, 14, 4706. <http://dx.doi.org/10.1039/c2ce25116g>
  • Yong Guo-Ping, Zhang Yi-Man, Zhang Bei: Hydrothermal syntheses, crystal structures and properties of novel quinone biradical and mixed-valence copper coordination polymer with semiquinone radical ligand generated in situ. CrystEngComm 2012, 14, 8620. <http://dx.doi.org/10.1039/c2ce26418h>
  • Wang Chao, Ma Yue, Wang Yali, Wang Qinglun, Li Licun, Cheng Peng, Liao Daizheng: A New Quinoxalinyl-Substituted Nitronyl Nitroxide Radical and its Five-Spin CuII and Four-Spin MnII Complexes: Syntheses, Crystal Structures, and Magnetic Properties. Aust. J. Chem. 2012, 65, 672. <http://dx.doi.org/10.1071/CH12077>
  • Baskett Martha, Paduan-Filho Armando, Oliveira Nei Fernandes, Chandrasekaran A., Mague Joel T., Lahti Paul M.: Loops, Chains, Sheets, and Networks from Variable Coordination of Cu(hfac)2 with a Flexibly Hinged Aminoxyl Radical Ligand. Inorg Chem 2011, 50, 5060. <http://dx.doi.org/10.1021/ic200362c>
  • Yong Guo-Ping, Li Ying-Zhou, Li Chong-Fu, Zhang Yi-Man, She Wen-Long: New metal-anion radical framework materials: CoII compounds showing ferromagnetic to antiferromagnetic phase transition at about 344 K, and ZnII compounds exhibiting terminal anion ligand induced direct white-light-emission. Dalton Trans 2011, 40, 4131. <http://dx.doi.org/10.1039/c0dt01667e>
  • Buzykin B. I.: Formazans in the synthesis of heterocycles. II. Synthesis of azines (Review). Chem Heterocycl Compd 2010, 46, 1043. <http://dx.doi.org/10.1007/s10593-010-0626-7>
  • Zhang Fa, Liu YouCheng: Electron transfer reactions of piperidine aminoxyl radicals. Chinese Sci Bull 2010, 55, 2760. <http://dx.doi.org/10.1007/s11434-010-3255-8>
  • Jung Martin, Sharma Ajay, Hinderberger Dariush, Braun Sebastian, Schatzschneider Ulrich, Rentschler Eva: Nitronyl Nitroxide Radicals Linked to Exchange-Coupled Metal Dimers - Studies Using X-ray Crystallography, Magnetic Susceptibility Measurements, EPR Spectroscopy, and DFT Calculations. Eur J Inorg Chem 2009, 2009, 1495. <http://dx.doi.org/10.1002/ejic.200801248>
  • Okazawa Atsushi, Nogami Takashi, Ishida Takayuki: Strong intramolecular ferromagnetic couplings in nickel(II) and copper(II) complexes chelated with tert-butyl 5-methoxy-2-pyridyl nitroxide. J Polyhedron 2009, 28, 1917. <http://dx.doi.org/10.1016/j.poly.2008.10.049>
  • Conway Sandra, Keeney Lynette, Hynes Michael J.: Anomalously slow rates of reduction of iron(III) polypyridine complexes by triphenyl verdazyl radicals in acetonitrile. Dalton Trans 2009, 2878. <http://dx.doi.org/10.1039/b818766e>
  • Kazazić Snježana P., Klasinc Leo, Rožman Marko, Srzić Dunja: The gas-phase interactions of TEMPO radicals with Fe+ ions. Rapid Commun Mass Spectrom 2008, 22, 2104. <http://dx.doi.org/10.1002/rcm.3596>
  • Lahti Paul M., Baskett Martha, Field Lora M., Carmen Morón M., Palacio Fernando, Paduan-Filho Armando, Oliveira Nei Fernandes: Isostructural M(RL)2(hfac)2 complexes with RL=5-(4-[N-tert-butyl-N-aminoxyl]phenyl)pyrimidine. Inorg Chim Ada 2008, 361, 3697. <http://dx.doi.org/10.1016/j.ica.2008.03.105>
  • Roques Nans, Maspoch Daniel, Luis Fernando, Camón Agustín, Wurst Klaus, Datcu Angela, Rovira Concepció, Ruiz-Molina Daniel, Veciana Jaume: A hexacarboxylic open-shell building block: synthesis, structure and magnetism of a three-dimensional metal–radical framework. J Mater Chem 2008, 18, 98. <http://dx.doi.org/10.1039/b713705b>
  • Roy Amit Saha, Muresan Nicoleta, Tuononen Heikki M., Rath Sankar P., Ghosh Prasanta: Electronic structure of the glyoxalbis(2-hydroxyanil) (gha) ligand in [CoIII(gha)(PPh3)2]+: radical vs. non-radical states. Dalton Trans 2008, 3438. <http://dx.doi.org/10.1039/b802063a>
  • Roques Nans, Perruchas Sandrine, Maspoch Daniel, Datcu Angela, Wurst Klaus, Sutter Jean-Pascal, Rovira Concepció, Veciana Jaume: Europium (III) complexes derived from carboxylic-substituted polychlorotriphenylmethyl radicals. Inorg Chim Ada 2007, 360, 3861. <http://dx.doi.org/10.1016/j.ica.2007.03.021>
  • Okazawa Atsushi, Nogami Takashi, Ishida Takayuki: Preparation, structures, and magnetic properties of precursors for chelating compounds of 2-pyridyl nitroxide derivatives. J Polyhedron 2007, 26, 1965. <http://dx.doi.org/10.1016/j.poly.2006.09.047>
  • Chahma M’hamed, Macnamara Keely, van der Est Art, Alberola Antonio, Polo Victor, Pilkington Melanie: Synthesis and characterization of a TTF-π-verdazyl radical—a new building block for conducting and/or magnetic systems. New J Chem 2007, 31, 1973. <http://dx.doi.org/10.1039/b706049a>
  • Boubekeur Kamal, Syssa-Magalé Jean-Laurent, Palvadeau Pierre, Schöllhorn Bernd: Self-assembly of nitroxide radicals via halogen bonding—directional NO⋯I interactions. Tetrahetron Lett 2006, 47, 1249. <http://dx.doi.org/10.1016/j.tetlet.2005.12.088>
  • Jennings Michael, Preuss Kathryn E., Wu Jian: Synthesis and magnetic properties of a 4-(2′-pyrimidyl)-1,2,3,5-dithiadiazolyl dimanganese complex. Chem Commun 2006, 341. <http://dx.doi.org/10.1039/b512312g>
  • Catala Laure, Wurst Klaus, Amabilino David B., Veciana Jaume: Polymorphs of a pyrazole nitronyl nitroxide and its complexes with metal(ii) hexafluoroacetylacetonates. J Mater Chem 2006, 16, 2736. <http://dx.doi.org/10.1039/b604598g>
  • Hideg Kálmán, Kálai Tamás, Sár Cecília P.: Recent results in chemistry and biology of nitroxides. J Heterocyclic Chem 2005, 42, 437. <http://dx.doi.org/10.1002/jhet.5570420311>
  • Beaulac Rémi, Luneau Dominique, Reber Christian: The emitting state of the imino nitroxide radical. chem phys letts 2005, 405, 153. <http://dx.doi.org/10.1016/j.cplett.2005.02.024>
  • Baskett Martha, Lahti Paul M.: Crystallography and magnetism of 3-(N-tert-butyl-N-aminoxyl)benzoic acid. J Polyhedron 2005, 24, 2645. <http://dx.doi.org/10.1016/j.poly.2005.03.144>
  • Field Lora M., Lahti Paul M.: Chain versus dimer contacts in crystalline 5-(4-[N-tert-butyl-N-aminoxyl]phenyl)pyrimidine radicals: Choices among competing intermolecular exchange mechanisms. J Polyhedron 2005, 24, 2639. <http://dx.doi.org/10.1016/j.poly.2005.03.145>
  • Paré Emily C., Brook David J. R., Brieger Aaron, Badik Mick, Schinke Marie: Synthesis of 1,5-diisopropyl substituted 6-oxoverdazyls. Org Biomol Chem 2005, 3, 4258. <http://dx.doi.org/10.1039/b510075e>
  • Lemaire Martin T.: Recent Developments in the Coordination Chemistry of Stable Free Radicals. ChemInform 2004, 35. <http://dx.doi.org/10.1002/chin.200431229>