Inorganic Chemistry
Article
the Oxidation of Geraniol to Geranial (2,6-Octadienal,3,7-dimethyl-,
(2E)-). Org. Sythn. 2005, 82, 80−86. (c) Ovcharenko, V. Metal-
Nitroxide Complexes: Synthesis and Magnetostructural Correlations.
In Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron
Compounds; Hicks, R. G., Ed.; John Wiley & Sons: West Sussex, UK,
2010; Chapter 13, pp 461−506. (d) Song, C.; Hu, K.-N.; Joo, C.-G.;
Swager, T. M.; Griffin, R. G. TOTAPOL: A Biradical Polarizing Agent
for Dynamic Nuclear Polarization Experiments in Aqueous Media. J.
Am. Chem. Soc. 2006, 128 (35), 11385−11390.
(2) Rosen, G. M.; Porasuphatana, S.; Tsai, P.; Ambulos, N. P.;
Galtsev, V. E.; Ichikawa, K.; Halpern, H. J. Dendrimeric-Containing
Nitronyl Nitroxides as Spin Traps for Nitric Oxide: Synthesis, Kinetic,
and Stability Studies. Macromolecules 2003, 36, 1021−1027.
(3) Francese, G.; Dunand, F. A.; Loosli, C.; Merbach, A. E.;
Decurtins, S. Functionalization of PAMAM dendrimers with nitronyl
nitroxide radicals as models for the outer-sphere relaxation in dentritic
potential MRI contrast agents. Magn. Reson. Chem. 2003, 41, 81−83.
(4) Yoshida, E.; Terazono, T. Synthesis of Model A5B1 Heteroarm
Star Copolymers Using Living Radical Polymerization Mediated by
2,2,6,6-Tetramethylpiperidine-1-oxyl. Polym. J. (Tokyo, Jpn.) 1999, 31
(7), 621−624.
and Report on a New Efficient Synthetic Route. Chem. - Eur. J. 2001, 7
(9), 2007−2014.
(17) Zoppellaro, G.; Geies, A.; Enkelmann, V.; Baumgarten, M. 2,6-
Bis(pyrazolyl)pyridine Functionalised with Two Nitronylnitroxide and
Iminonitroxide Radicals. Eur. J. Org. Chem. 2004, 2004, 2367−2374.
(18) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G.
Solvophobically Driven Folding of Nonbiological Oligomers. Science
1997, 277 (5333), 1793−1796.
(19) Ravat, P.; Ito, Y.; Gorelik, E.; Enkelmann, V.; Baumgarten, M.
Tetramethoxypyrene-Based Biradical Donors with Tunable Physical
and Magnetic Properties. Org. Lett. 2013, 15 (17), 4280−4283.
(20) Budnikova, Y. G.; Gryaznova, T. V.; Kadirov, M. K.; Tretyakov,
E. V.; Kholin, K. V.; Ovcharenko, V. I.; Sagdeev, R. Z.; Sinyashin, O. G.
Electrochemistry of Nitronyl and Imino Nitroxides. Russ. J. Phys. Chem.
A 2009, 83 (11), 1976−1980.
(21) Vuki, M.; Shiu, K.-K.; Galik, M.; O’Mahony, A. M.; Wang, J.
Simultaneous electrochemical measurement of metal and organic
propellant constituents of gunshot residues. Analyst 2012, 137, 3265−
3270.
(22) Onal, E.; Yerli, Y.; Cosut, B.; Pilet, G.; Ahsen, V.; Luneau, D.;
Hirel, C. Nitronyl and imino nitroxide free radicals as precursors of
magnetic phthalocyanine and porphyrin building blocks. New J. Chem.
2014, 38, 4440−4447.
(23) Korkut, S. E.; Akyuz, D.; Ozdogan, K.; Yerli, Y.; Koca, A.; Sener,
M. K. TEMPO-functionalized zinc phthalocyanine: synthesis,
magnetic properties, and its utility for electrochemical sensing of
ascorbic acid. Dalton Trans. 2016, 45, 3086−3092.
(24) Patil, B. R.; Machakanur, S. S.; Badiger, D. S.; Hunoor, R. S.;
Gudasi, K. B.; Nethaji, M.; Bligh, S. W. A. Hexa-arm star shaped
hydrazone derivatives from hexakis(4-formylphenoxy)-cyclotriphos-
phazene core. J. Mol. Struct. 2011, 1003, 52−61.
(25) Ranchet, D.; Tommasino, J. B.; Vittori, O.; Fabre, P. L. Solvent
Effects on the Electrochemical Behavior of Iron(III) Schiff Base
Complex. J. Solution Chem. 1998, 27 (11), 979−91.
(26) Bruker. SADABS; Bruker AXS Inc.: Madison, WI, 2005.
(27) Bruker. APEX2; Bruker AXS Inc.: Madison, WI, 2008.
(28) Sheldrick, G. A short history of SHELX. Acta Crystallogr., Sect.
A: Found. Crystallogr. 2008, 64, 112−122.
(29) Pascal, P. Recherches Magnetochimique. Ann. Chim. Phys. 1910,
19, 5−70.
(5) Shimono, S.; Tamura, R.; Ikuma, N.; Takahashi, H.; Sakai, N.;
Yamauchi, J. Characterization of the Chiral Paramagnetic Multispin
System Built on a Cyclotriphosphazene Scaffold. Chem. Lett. 2004, 33
(7), 932−933.
(6) Shimono, S.; Takahashi, H.; Sakai, N.; Tamura, R.; Ikuma, N.;
Yamauchi, J. Use of Cyclotriphosphazene as a Molecular Scaffold for
Building Chiral Multispin Systems. Mol. Cryst. Liq. Cryst. 2005, 440:1,
37−52.
(7) Dulog, L.; Mohler, H. A λ5-cylotriphosphazene with nitroxyl
groups as model for a paramagnetic poly(organo-λ5-phosp hazene).
Makromol. Chem. 1988, 189, 2611−2615.
(8) Badetti, E.; Lloveras, V.; Wurst, K.; Sebastian, R. M.; Caminade,
A.-M.; Majoral, J.-P.; Veciana, J.; Vidal-Gancedo, J. Synthesis and
Structural Characterization of a Dendrimer Model Compound Based
on a Cyclotriphosphazene Core with TEMPO Radicals as Sub-
stituents. Org. Lett. 2013, 15 (14), 3490−93.
(9) Badetti, E.; Lloveras, V.; Munoz-Gomez, J. L.; Sebastian, R. M.;
Caminade, A.-M.; Majoral, J.-P.; Veciana, J.; Vidal-Gancedo, J. Radical
Dendrimers: A Family of Five Generations of Phosphorus Dendrimers
Functionalized with TEMPO Radicals. Macromolecules 2014, 47,
7717−24.
(10) Carriedo, G. A.; Fernandez-Catuxo, L.; Alonso, F. J. G.; Elipe, P.
G.; Gonzalez, P. A.; Sanchez, G. On the Synthesis of Functionalized
Cyclic and Polymeric Aryloxyphosphazenes from Phenols. J. Appl.
Polym. Sci. 1996, 59, 1879−1885.
(30) (a) Sayre, R. The Identity of Heilpern’s “Pinacolylthiourea” and
the Preparation of Authentic 2-Thiono-4,4,5,5-tetramethylimidazoli-
dine. J. Am. Chem. Soc. 1955, 77 (24), 6689−6690. (b) Hirel, C.
Radicaux Libres Nitronyl Nitroxyde Chiraux: Sytnhese et Proprietes
de Coordination. Ph.D. Thesis, Universite Joseph Fourier Grenoble1,
Grenoble, France, 1999.
(11) Yuan, W.; Tang, X.; Huang, X.; Zheng, S. Synthesis,
characterization and thermal properties of hexaarmed star-shaped
poly(ε-caprolactone)-b-poly(D,L-lactide-co-glycolide) initiated with
hydroxyl-terminated cyclotriphosphazene. Polymer 2005, 46, 1701−
1707.
(12) Kagit, R.; Yildirim, M.; Ozay, O.; Yesilot, S.; Ozay, H.
Phosphazene Based Multicentered Naked-Eye Fluorescent Sensor
with High Selectivity for Fe3+ Ions. Inorg. Chem. 2014, 53, 2144−2151.
(13) Bertani, R.; Chaux, F.; Gleria, M.; Metrangolo, P.; Milani, R.;
Pilati, T.; Resnati, G.; Sansotera, M.; Venza, A. Supramolecular rods
via halogen bonding-based self-assembly of fluorinated phosphazene
nanopillars. Inorg. Chim. Acta 2007, 360, 1191−1199.
(14) Ullman, E. F.; Osiecki, J. H.; Boocock, D. G. B.; Darcy, R.
Studies of Stable Free Radicals. X. Nitronyl Nitroxide Monoradicals
and Biradicals as Possible Small Molecule Spin Labels. J. Am. Chem.
Soc. 1972, 94 (20), 7049−7059.
(15) Shimono, S.; Tamura, R.; Ikuma, N.; Takimoto, T.; Kawame,
N.; Tamada, O.; Sakai, N.; Matsuura, H.; Yamauchi, J. Preparation and
Characterization of New Chiral Nitronyl Nitroxides Bearing a
Stereogenic Center in the Imidazolyl Framework. J. Org. Chem.
2004, 69, 475−481.
(16) Hirel, C.; Vostrikova, K. E.; Pecaut, J.; Ovcharenko, V. I.; Rey, P.
Nitronyl and Imino Nitroxides: Improvement of Ullman’s Procedure
G
Inorg. Chem. XXXX, XXX, XXX−XXX