Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η5-C5H5) Fe(η5-C5H4)-C(p-MeC6 H4)=NNH-(η6-p-MeC6H4) Fe(η5-C5H5)]+PF 6                         -, and of its toluoylferrocene precursor

Walter Figueroa; Mauricio Fuentealba; Carolina Manzur; Andrés I. Vega; David Carrillo; Jean René Hamon

doi:10.1016/j.crci.2004.11.035

Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η⁵-C₅H₅) Fe(η⁵-C₅H₄)-C(p-MeC₆ H₄)=NNH-(η⁶-p-MeC₆H₄) Fe(η⁵-C₅H₅)]⁺PF ₆ ^-, and of its toluoylferrocene precursor

Walter Figueroa, Mauricio Fuentealba, Carolina Manzur, Andrés I. Vega, David Carrillo, Jean René Hamon

INSTITUTE OF CHEMISTRY

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Abstract

The homobimetallic hydrazone complex [CpFe(η⁶-p-CH ₃C₆H₄)NHN=C(C₆H₄ -p-CH₃)(η⁵-C₅H₄) FeCp]⁺PF₆ ^- (2) (Cp = η⁵ -C₅H₅) is stereoselectively formed by reaction of the organometallic hydrazine precursor [CpFe(η⁶-p-CH ₃C₆H₄-NHNH₂)]⁺ PF₆ ^- with the sterically demanding p-toluoylferrocene CpFe(η⁵-C₅H₄ )CO(C₆H₄-p-CH₃) (1) in refluxing ethanol. Compound 2 has been fully characterized by IR, UV-vis, and ¹H NMR spectroscopy, cyclic voltammetry and by an X-ray diffraction analysis. The most striking features of the crystal structure are the syn-conformation of the two organometallic units, the long Fe-C_ipso bond distances and the slight cyclohexadienyl character at the coordinated C₆ ring with a folding angle of 6.1°, and that coordinated C₆- and C₅-rings of the binucleating ligand are almost coplanar with a dihedral angle of 8.1°. The crystal structure of the p-toluoylferrocene 1 is also presented.

Original language	English
Pages (from-to)	1268-1275
Number of pages	8
Journal	Comptes Rendus Chimie
Volume	8
Issue number	8 SPEC. ISS.
DOIs	https://doi.org/10.1016/j.crci.2004.11.035
State	Published - Aug 2005

Keywords

Dipolar chromophores
Ferrocene complexes
Organoiron complexes
Organometallic hydrazone complexes
Push-pull complexes
X-ray structure

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10.1016/j.crci.2004.11.035

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Figueroa, W., Fuentealba, M., Manzur, C., Vega, A. I., Carrillo, D., & Hamon, J. R. (2005). Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η⁵-C₅H₅) Fe(η⁵-C₅H₄)-C(p-MeC₆ H₄)=NNH-(η⁶-p-MeC₆H₄) Fe(η⁵-C₅H₅)]⁺PF ₆ ^-, and of its toluoylferrocene precursor. Comptes Rendus Chimie, 8(8 SPEC. ISS.), 1268-1275. https://doi.org/10.1016/j.crci.2004.11.035

@article{ea7b69c265ce4eb4a1f89b0fa3400498,

title = "Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η5-C5H5) Fe(η5-C5H4)-C(p-MeC6 H4)=NNH-(η6-p-MeC6H4) Fe(η5-C5H5)]+PF 6 -, and of its toluoylferrocene precursor",

abstract = "The homobimetallic hydrazone complex [CpFe(η6-p-CH 3C6H4)NHN=C(C6H4 -p-CH3)(η5-C5H4) FeCp]+PF6 - (2) (Cp = η5 -C5H5) is stereoselectively formed by reaction of the organometallic hydrazine precursor [CpFe(η6-p-CH 3C6H4-NHNH2)]+ PF6 - with the sterically demanding p-toluoylferrocene CpFe(η5-C5H4 )CO(C6H4-p-CH3) (1) in refluxing ethanol. Compound 2 has been fully characterized by IR, UV-vis, and 1H NMR spectroscopy, cyclic voltammetry and by an X-ray diffraction analysis. The most striking features of the crystal structure are the syn-conformation of the two organometallic units, the long Fe-Cipso bond distances and the slight cyclohexadienyl character at the coordinated C6 ring with a folding angle of 6.1°, and that coordinated C6- and C5-rings of the binucleating ligand are almost coplanar with a dihedral angle of 8.1°. The crystal structure of the p-toluoylferrocene 1 is also presented.",

keywords = "Dipolar chromophores, Ferrocene complexes, Organoiron complexes, Organometallic hydrazone complexes, Push-pull complexes, X-ray structure",

author = "Walter Figueroa and Mauricio Fuentealba and Carolina Manzur and Vega, {Andr{\'e}s I.} and David Carrillo and Hamon, {Jean Ren{\'e}}",

note = "Funding Information: We thank the financial support from Fondo Nacional de Desarrollo Cient{\'i}fico y Tecnol{\'o}gico, FONDECYT (Chile), Grant No. 1010318 (D.C., C.M.), the CNRS-CONICYT Project No. 16771 (D.C., C.M., J.-R.H.), and the Vicerrector{\'i}a de Investigaci{\'o}n y Estudios Avanzados, Pontificia Universidad Cat{\'o}lica de Valpara{\'i}so, Chile.",

year = "2005",

month = aug,

doi = "10.1016/j.crci.2004.11.035",

language = "English",

volume = "8",

pages = "1268--1275",

journal = "Comptes Rendus Chimie",

issn = "1631-0748",

publisher = "Academie des sciences",

number = "8 SPEC. ISS.",

}

Figueroa, W, Fuentealba, M , Manzur, C, Vega, AI, Carrillo, D & Hamon, JR 2005, 'Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η⁵-C₅H₅) Fe(η⁵-C₅H₄)-C(p-MeC₆ H₄)=NNH-(η⁶-p-MeC₆H₄) Fe(η⁵-C₅H₅)]⁺PF ₆ ^-, and of its toluoylferrocene precursor', Comptes Rendus Chimie, vol. 8, no. 8 SPEC. ISS., pp. 1268-1275. https://doi.org/10.1016/j.crci.2004.11.035

Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η⁵-C₅H₅) Fe(η⁵-C₅H₄)-C(p-MeC₆ H₄)=NNH-(η⁶-p-MeC₆H₄) Fe(η⁵-C₅H₅)]⁺PF ₆ ^-, and of its toluoylferrocene precursor. / Figueroa, Walter; Fuentealba, Mauricio ; Manzur, Carolina et al.
In: Comptes Rendus Chimie, Vol. 8, No. 8 SPEC. ISS., 08.2005, p. 1268-1275.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η5-C5H5) Fe(η5-C5H4)-C(p-MeC6 H4)=NNH-(η6-p-MeC6H4) Fe(η5-C5H5)]+PF 6 -, and of its toluoylferrocene precursor

AU - Figueroa, Walter

AU - Fuentealba, Mauricio

AU - Manzur, Carolina

AU - Vega, Andrés I.

AU - Carrillo, David

AU - Hamon, Jean René

N1 - Funding Information: We thank the financial support from Fondo Nacional de Desarrollo Científico y Tecnológico, FONDECYT (Chile), Grant No. 1010318 (D.C., C.M.), the CNRS-CONICYT Project No. 16771 (D.C., C.M., J.-R.H.), and the Vicerrectoría de Investigación y Estudios Avanzados, Pontificia Universidad Católica de Valparaíso, Chile.

PY - 2005/8

Y1 - 2005/8

N2 - The homobimetallic hydrazone complex [CpFe(η6-p-CH 3C6H4)NHN=C(C6H4 -p-CH3)(η5-C5H4) FeCp]+PF6 - (2) (Cp = η5 -C5H5) is stereoselectively formed by reaction of the organometallic hydrazine precursor [CpFe(η6-p-CH 3C6H4-NHNH2)]+ PF6 - with the sterically demanding p-toluoylferrocene CpFe(η5-C5H4 )CO(C6H4-p-CH3) (1) in refluxing ethanol. Compound 2 has been fully characterized by IR, UV-vis, and 1H NMR spectroscopy, cyclic voltammetry and by an X-ray diffraction analysis. The most striking features of the crystal structure are the syn-conformation of the two organometallic units, the long Fe-Cipso bond distances and the slight cyclohexadienyl character at the coordinated C6 ring with a folding angle of 6.1°, and that coordinated C6- and C5-rings of the binucleating ligand are almost coplanar with a dihedral angle of 8.1°. The crystal structure of the p-toluoylferrocene 1 is also presented.

AB - The homobimetallic hydrazone complex [CpFe(η6-p-CH 3C6H4)NHN=C(C6H4 -p-CH3)(η5-C5H4) FeCp]+PF6 - (2) (Cp = η5 -C5H5) is stereoselectively formed by reaction of the organometallic hydrazine precursor [CpFe(η6-p-CH 3C6H4-NHNH2)]+ PF6 - with the sterically demanding p-toluoylferrocene CpFe(η5-C5H4 )CO(C6H4-p-CH3) (1) in refluxing ethanol. Compound 2 has been fully characterized by IR, UV-vis, and 1H NMR spectroscopy, cyclic voltammetry and by an X-ray diffraction analysis. The most striking features of the crystal structure are the syn-conformation of the two organometallic units, the long Fe-Cipso bond distances and the slight cyclohexadienyl character at the coordinated C6 ring with a folding angle of 6.1°, and that coordinated C6- and C5-rings of the binucleating ligand are almost coplanar with a dihedral angle of 8.1°. The crystal structure of the p-toluoylferrocene 1 is also presented.

KW - Dipolar chromophores

KW - Ferrocene complexes

KW - Organoiron complexes

KW - Organometallic hydrazone complexes

KW - Push-pull complexes

KW - X-ray structure

UR - http://www.scopus.com/inward/record.url?scp=21144444385&partnerID=8YFLogxK

U2 - 10.1016/j.crci.2004.11.035

DO - 10.1016/j.crci.2004.11.035

M3 - Article

AN - SCOPUS:21144444385

SN - 1631-0748

VL - 8

SP - 1268

EP - 1275

JO - Comptes Rendus Chimie

JF - Comptes Rendus Chimie

IS - 8 SPEC. ISS.

ER -

Figueroa W, Fuentealba M , Manzur C, Vega AI, Carrillo D, Hamon JR. Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η⁵-C₅H₅) Fe(η⁵-C₅H₄)-C(p-MeC₆ H₄)=NNH-(η⁶-p-MeC₆H₄) Fe(η⁵-C₅H₅)]⁺PF ₆ ^-, and of its toluoylferrocene precursor. Comptes Rendus Chimie. 2005 Aug;8(8 SPEC. ISS.):1268-1275. doi: 10.1016/j.crci.2004.11.035

Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η⁵-C₅H₅) Fe(η⁵-C₅H₄)-C(p-MeC₆ H₄)=NNH-(η⁶-p-MeC₆H₄) Fe(η⁵-C₅H₅)]⁺PF ₆ ^-, and of its toluoylferrocene precursor

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