Organodiiron(II)-complexes containing a long conjugated hydrazonato spacer. Synthesis, charcterization, electrochemical and structural studies

Carolina Manzur; Mauricio Fuentealba; Lorena Millán; Francisco Gajardo; Maria Teresa Garland; Ricardo Baggio; Jose A. Mata; Jean René Hamon; David Carrillo

doi:10.1016/S0022-328X(02)01769-2

Organodiiron(II)-complexes containing a long conjugated hydrazonato spacer. Synthesis, charcterization, electrochemical and structural studies

Carolina Manzur, Mauricio Fuentealba, Lorena Millán, Francisco Gajardo, Maria Teresa Garland, Ricardo Baggio, Jose A. Mata, Jean René Hamon, David Carrillo

INSTITUTE OF CHEMISTRY

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Abstract

Organometallic hydrazines of general formula Me, (2)⁺PF₆^-; MeO, (3)⁺ PF₆^-; Cl, (4)⁺PF₆ ^-) react with equimolar quantities of (E)-4- (2-ferrocenylvinyl)-benzaldehyde, (E)-[(η⁵-Cp) Fe(η⁵-C₅H₄)-CH=CH-C ₆H₄CHO], to afford stereoselectively, the new homodimetallic hydrazones formulated as (E)-[(η5-Cp) Fe(η⁶-p-RC₆H₄)-NHN=CH- C₆H₄=CH-CH-(η⁵-C₅ H₄)Fe(η⁵-Cp)]⁺PF₆ ^- (R=H, (5)⁺PF₆^-; Me, (6)⁺PF₆^-; MeO, (7)⁺PF ₆^-; Cl, (8)⁺PF₆^-). These compounds were fully characterized by elemental analysis and spectroscopic techniques (¹H-and ¹³C-NMR, IR and UV-vis) and, in the case of complex (6)⁺PF₆ ^-, by single crystal X-ray diffraction methods. The rotations of the ferrocenyl unit by 37.2 out of the -NHN-CH-C₆H ₄=CH-CH- spacer and coordinated phenyl ring planes, may generate an unfavorable structure to allow π-electron delocalization along the entire hydrazonato backbone between the two metals separated through bonds by more than 1.8 nm, as confirmed by the electrochemical data.

Original language	English
Pages (from-to)	71-77
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	660
Issue number	1
DOIs	https://doi.org/10.1016/S0022-328X(02)01769-2
State	Published - 7 Oct 2002

Keywords

Arenehydrazone-iron complex
Bimetallic complex
Cyclopentadienyl-iron complex
Nanomolecule
Sandwich complex
X-ray structure

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10.1016/S0022-328X(02)01769-2

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Manzur, C., Fuentealba, M., Millán, L., Gajardo, F., Garland, M. T., Baggio, R., Mata, J. A., Hamon, J. R., & Carrillo, D. (2002). Organodiiron(II)-complexes containing a long conjugated hydrazonato spacer. Synthesis, charcterization, electrochemical and structural studies. Journal of Organometallic Chemistry, 660(1), 71-77. https://doi.org/10.1016/S0022-328X(02)01769-2

@article{a7846991de574e4f9fe50c9f353ef43c,

title = "Organodiiron(II)-complexes containing a long conjugated hydrazonato spacer. Synthesis, charcterization, electrochemical and structural studies",

abstract = "Organometallic hydrazines of general formula Me, (2)+PF6-; MeO, (3)+ PF6-; Cl, (4)+PF6 -) react with equimolar quantities of (E)-4- (2-ferrocenylvinyl)-benzaldehyde, (E)-[(η5-Cp) Fe(η5-C5H4)-CH=CH-C 6H4CHO], to afford stereoselectively, the new homodimetallic hydrazones formulated as (E)-[(η5-Cp) Fe(η6-p-RC6H4)-NHN=CH- C6H4=CH-CH-(η5-C5 H4)Fe(η5-Cp)]+PF6 - (R=H, (5)+PF6-; Me, (6)+PF6-; MeO, (7)+PF 6-; Cl, (8)+PF6-). These compounds were fully characterized by elemental analysis and spectroscopic techniques (1H-and 13C-NMR, IR and UV-vis) and, in the case of complex (6)+PF6 -, by single crystal X-ray diffraction methods. The rotations of the ferrocenyl unit by 37.2 out of the -NHN-CH-C6H 4=CH-CH- spacer and coordinated phenyl ring planes, may generate an unfavorable structure to allow π-electron delocalization along the entire hydrazonato backbone between the two metals separated through bonds by more than 1.8 nm, as confirmed by the electrochemical data.",

keywords = "Arenehydrazone-iron complex, Bimetallic complex, Cyclopentadienyl-iron complex, Nanomolecule, Sandwich complex, X-ray structure",

author = "Carolina Manzur and Mauricio Fuentealba and Lorena Mill{\'a}n and Francisco Gajardo and Garland, {Maria Teresa} and Ricardo Baggio and Mata, {Jose A.} and Hamon, {Jean Ren{\'e}} and David Carrillo",

note = "Funding Information: The authors gratefully acknowledge Fondo Nacional de Desarrollo Cient{\'ı}fico y Tecnol{\'o}gico, FONDECYT (Chile), Grant No 1010318 (D.C., C.M.), to the PICS No 922 CNRS (France)-CONICYT (Chile) (C.M., D.C., J.-R.H., M.T.G.), to Fundaci{\'o}n Andes for funding the purchase of the Single-Crystal Diffractometer (M.-T.G., R.B.) and to the Vicerrector{\'ı}a de Investigaci{\'o}n y Estudios Avanzados, Universidad Cat{\'o}lica de Valpara{\'ı}so, Chile.",

year = "2002",

month = oct,

day = "7",

doi = "10.1016/S0022-328X(02)01769-2",

language = "English",

volume = "660",

pages = "71--77",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "1",

}

Manzur, C , Fuentealba, M, Millán, L, Gajardo, F, Garland, MT, Baggio, R, Mata, JA, Hamon, JR & Carrillo, D 2002, 'Organodiiron(II)-complexes containing a long conjugated hydrazonato spacer. Synthesis, charcterization, electrochemical and structural studies', Journal of Organometallic Chemistry, vol. 660, no. 1, pp. 71-77. https://doi.org/10.1016/S0022-328X(02)01769-2

TY - JOUR

T1 - Organodiiron(II)-complexes containing a long conjugated hydrazonato spacer. Synthesis, charcterization, electrochemical and structural studies

AU - Manzur, Carolina

AU - Fuentealba, Mauricio

AU - Millán, Lorena

AU - Gajardo, Francisco

AU - Garland, Maria Teresa

AU - Baggio, Ricardo

AU - Mata, Jose A.

AU - Hamon, Jean René

AU - Carrillo, David

N1 - Funding Information: The authors gratefully acknowledge Fondo Nacional de Desarrollo Cientı́fico y Tecnológico, FONDECYT (Chile), Grant No 1010318 (D.C., C.M.), to the PICS No 922 CNRS (France)-CONICYT (Chile) (C.M., D.C., J.-R.H., M.T.G.), to Fundación Andes for funding the purchase of the Single-Crystal Diffractometer (M.-T.G., R.B.) and to the Vicerrectorı́a de Investigación y Estudios Avanzados, Universidad Católica de Valparaı́so, Chile.

PY - 2002/10/7

Y1 - 2002/10/7

N2 - Organometallic hydrazines of general formula Me, (2)+PF6-; MeO, (3)+ PF6-; Cl, (4)+PF6 -) react with equimolar quantities of (E)-4- (2-ferrocenylvinyl)-benzaldehyde, (E)-[(η5-Cp) Fe(η5-C5H4)-CH=CH-C 6H4CHO], to afford stereoselectively, the new homodimetallic hydrazones formulated as (E)-[(η5-Cp) Fe(η6-p-RC6H4)-NHN=CH- C6H4=CH-CH-(η5-C5 H4)Fe(η5-Cp)]+PF6 - (R=H, (5)+PF6-; Me, (6)+PF6-; MeO, (7)+PF 6-; Cl, (8)+PF6-). These compounds were fully characterized by elemental analysis and spectroscopic techniques (1H-and 13C-NMR, IR and UV-vis) and, in the case of complex (6)+PF6 -, by single crystal X-ray diffraction methods. The rotations of the ferrocenyl unit by 37.2 out of the -NHN-CH-C6H 4=CH-CH- spacer and coordinated phenyl ring planes, may generate an unfavorable structure to allow π-electron delocalization along the entire hydrazonato backbone between the two metals separated through bonds by more than 1.8 nm, as confirmed by the electrochemical data.

AB - Organometallic hydrazines of general formula Me, (2)+PF6-; MeO, (3)+ PF6-; Cl, (4)+PF6 -) react with equimolar quantities of (E)-4- (2-ferrocenylvinyl)-benzaldehyde, (E)-[(η5-Cp) Fe(η5-C5H4)-CH=CH-C 6H4CHO], to afford stereoselectively, the new homodimetallic hydrazones formulated as (E)-[(η5-Cp) Fe(η6-p-RC6H4)-NHN=CH- C6H4=CH-CH-(η5-C5 H4)Fe(η5-Cp)]+PF6 - (R=H, (5)+PF6-; Me, (6)+PF6-; MeO, (7)+PF 6-; Cl, (8)+PF6-). These compounds were fully characterized by elemental analysis and spectroscopic techniques (1H-and 13C-NMR, IR and UV-vis) and, in the case of complex (6)+PF6 -, by single crystal X-ray diffraction methods. The rotations of the ferrocenyl unit by 37.2 out of the -NHN-CH-C6H 4=CH-CH- spacer and coordinated phenyl ring planes, may generate an unfavorable structure to allow π-electron delocalization along the entire hydrazonato backbone between the two metals separated through bonds by more than 1.8 nm, as confirmed by the electrochemical data.

KW - Arenehydrazone-iron complex

KW - Bimetallic complex

KW - Cyclopentadienyl-iron complex

KW - Nanomolecule

KW - Sandwich complex

KW - X-ray structure

UR - http://www.scopus.com/inward/record.url?scp=0037037379&partnerID=8YFLogxK

U2 - 10.1016/S0022-328X(02)01769-2

DO - 10.1016/S0022-328X(02)01769-2

M3 - Article

AN - SCOPUS:0037037379

SN - 0022-328X

VL - 660

SP - 71

EP - 77

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1

ER -

Organodiiron(II)-complexes containing a long conjugated hydrazonato spacer. Synthesis, charcterization, electrochemical and structural studies

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