Structures and properties of ferrocene derivatives with different kinds of nitroxide radicals

Nakatsuji, Shin’ichi; Fujiwara, K.; Akutsu, Hiroki; Yamada, Jun−ichi; Satoh, Masaharu

doi:10.1039/c3nj00343d

Cited by 4 publications

(3 citation statements)

References 22 publications

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“…The structure of UDUJAF has an s-cis configuration of the acrylate residues (Suzaki & Osakada, 2007). Only four simple ferrocenylmethyl esters have been described previously (Suzaki & Osakada, 2007;Nakatsuji et al, 2013), however, more complex biferrocene (Dong et al, 1997) and 1,2-substituted examples have been reported (Stepnicka & Cisarova, 2002;Pé rez et al, 2012). Interestingly, of the reported methacrylate structures, only ten display a C-HÁ Á Á(alkene) contact similar to that observed for (I) (see, for example: Hirano et al, 2002;Banwell et al, 2003;Wu et al, 2011;El Aziz et al, 2012;Kong et al, 2012), but none of these reports detailed this contact.…”

Section: Figurementioning

confidence: 99%

Structures and packing of ferrocenylmethyl methacrylate and ferrocene-1,1′-diylbis(methylene) dimethacrylate

McAdam

Moratti

2015

Acta Crystallogr C

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Electroactive metallocene polymers are of interest due to the possibility that they offer a muscle-like response, and in gel systems very large volume changes are possible. The ferrocenyl moiety exhibits physical and electrochemical stability of the neutral and oxidized forms and could be a candidate for use as the redox-active group in these materials. The title compounds, [Fe(C5H5)(C10H11O2)], (I), and [Fe(C10H11O2)2], (II), comprise a typical ferrocene core with coplanar and approximately eclipsed cyclopentadienyl (Cp) rings. In (I), there is a single methyl methacrylate substituent, with the other Cp ring unsubstituted. In (II), a methyl methacrylate substituent on each Cp ring completes the structure. In both compounds, there is an s-trans geometry of the vinyl and carbonyl components of the methacrylate group. Inversion dimers formed through C-H...O contacts dominate the crystal packing of both molecules. Weak C-H...π(ring) contacts and, in the case of (I), an unusual C-H...π(alkene) contact further stabilize the structures.

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Section: Figurementioning

confidence: 99%

Structures and packing of ferrocenylmethyl methacrylate and ferrocene-1,1′-diylbis(methylene) dimethacrylate

McAdam

Moratti

2015

Acta Crystallogr C

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“…High efficiency of Pd-catalyzed cross-coupling reactions of organogold carbene-like derivatives of 2-imidazoline nitronyl nitroxides with aryl- and vinyl-halides has been demonstrated as a reliable methodological tool for the obtaining of nitroxide types unavailable by other synthetic routes [ 12 , 13 , 14 , 15 , 16 , 17 ]. It has been shown that the introduction of various nitroxide substituents into ferrocene can also serve as a fruitful approach by which peculiar types of molecular magnets [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ], spin labels with tunable spacing between different types of paramagnetic centers [ 36 , 37 ], miniature fast-charging electrochemical elements [ 38 , 39 ], and paramagnets with antioxidant activity have been obtained [ 40 ].…”

Section: Introductionmentioning

confidence: 99%

2-Imidazoline Nitroxide Derivatives of Cymantrene

et al. 2022

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The 2-imidazoline nitroxide derivatives of cymantrene—2-(η5-cyclopentadienyl)tricarbonylmanganese(I)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl (NNMn) and 2-(η5-cyclopentadienyl)tricarbonylmanganese(I)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-1-oxyl (INMn) were synthesized. It was shown that NNMn and INMn exhibit a sufficiently high kinetic stability both in solids and in solutions under normal conditions. Their structural characteristics, magnetic properties and electrochemical behavior are close to Re(I) analogs. This opens the prospect of using paramagnetic cymantrenes as prototypes in the design of Re(I) half-sandwiched derivatives for theranostics, where therapy is combined with diagnostics by magnetic resonance imaging due to the contrast properties of nitroxide radicals.

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“…However, the synthesis and physicochemical properties of such compounds are a scarce studied area of organometallic chemistry. Previously, a ferrocene and ruthenocene/osmocene species substituted with various nitroxide fragments have been extensively explored, while other nitroxide-bound derivatives of metallocenes, [10][11][12][13][14][15] including half-sandwich ones, are still unknown. We succeeded in synthesizing organometallic complexes [(RCp)Re(CO) 3 ] bearing nitroxide substituents R that could be used as a convenient approach in the design of paramagnetic targeted drugs for theranostics.…”

Section: Introductionmentioning

confidence: 99%