1′,1′′′-Bis(ethynyl)biferrocene as a Linking Group for Gold, Ruthenium, and Osmium Fragments: Synthesis, Solid State Structures, and Electrochemical, UV−Vis, and EPR Spectroscopical Studies

A series of organometallic mono- and disubstituted bis(alkynyl)biferrocenes of type (LnMCC)(HCC)bfc (LnM = (η5-C5H5)(Ph3P)2Ru (8a), (η5-C5H5)(Ph3P)2Os (8b), (η5-C5H5)(dppf)Ru (8c); bfc = 1′,1′′′-biferrocenyl, ((η5-C5H4)2Fe)2; dppf = 1,1′-bis(diphenyl)phosphanyl ferrocene, (η5-C5H4PPh2)2Fe) and (Ln...

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Published inOrganometallics Vol. 28; no. 6; pp. 1878 - 1890
Main Authors Lohan, Manja, Ecorchard, Petra, Rüffer, Tobias, Justaud, Frédéric, Lapinte, Claude, Lang, Heinrich
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.03.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVE FERROCENYL SPACER
TRANSITION-METAL-COMPLEXES
INTRAMOLECULAR ELECTRON-TRANSFER
FE-57 MOSSBAUER CHARACTERISTICS
CRYSTAL-STRUCTURE
CYCLOPENTADIENYL-RUTHENIUM
MIXED-VALENCE COMPLEXES
ACETYLIDE COMPLEXES
PHOTOPHYSICAL PROPERTIES
TERPYRIDINE COMPLEXES
Online AccessGet full text
ISSN0276-7333
1520-6041
DOI10.1021/om8011344

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Abstract A series of organometallic mono- and disubstituted bis(alkynyl)biferrocenes of type (LnMCC)(HCC)bfc (LnM = (η5-C5H5)(Ph3P)2Ru (8a), (η5-C5H5)(Ph3P)2Os (8b), (η5-C5H5)(dppf)Ru (8c); bfc = 1′,1′′′-biferrocenyl, ((η5-C5H4)2Fe)2; dppf = 1,1′-bis(diphenyl)phosphanyl ferrocene, (η5-C5H4PPh2)2Fe) and (LnMCC)2bfc (LnM = (Ph3P)Au (6), (η5-C5H5)(Ph3P)2Ru (9a), (η5-C5H5)(Ph3P)2Os (9b), (η5-C5H5)(dppf)Ru (9c)) have been synthesized from (HCC)2bfc (4) with either (Ph3P)AuCl (5) in the presence of HNEt2/[CuI] (synthesis of 6) or LnMX (LnMX = (η5-C5H5)(Ph3P)2RuCl (7a); (η5-C5H5)(Ph3P)2OsBr (7b); (η5-C5H5)(dppf)RuCl (7c)) together with [H4N]PF6 and KOtBu (synthesis of 8 and 9), respectively. The structures of 6, 8b, 9a, 9b, and 9c in the solid state were determined by single-crystal X-ray structure analysis, showing unsymmetrical (8) or symmetrical geometries (6, 9), with almost eclipsed conformations or approximately midway positions between the fully eclipsed and the fully staggered conformation of the bfc cyclopentadienyl rings and with anti geometry of the linear ethynyl connecting units. UV−vis and NIR spectroscopic measurements suggest a weak interaction between the appropriate metal atoms. The associated radical cations were in situ generated by stepwise chemical oxidation and characterized by continuous wave electron paramagnetic resonance (EPR) investigations in X-band performed at low temperature.
AbstractList A series of orgarrometallic mono- and disubstituted bis(alkynyl)biferrocenes of type (LnMC C)-(HC C)bfc (LnM = (eta(5)-C5H5)(Ph3P)(2)Ru (8a), (eta(5)-C5H5)(Ph3P)(2)Os (8b), (eta(5)-C5H5)(dppf)Ru (8c); bfc = 1',1'''-biferrocenyl, ((eta(5)-C5H4)(2)Fe)(2); dppf = 1,1'-bis(diphenyl)phosphanyl ferrocene, (eta(5)-C5H4PPh2)(2)Fe) and (LnMC C)(2)bfc (LnM = (Ph3P)Au (6), (eta(5)-C5H5)(Ph3P)(2)Ru (9a), (eta(5)-C5H5)(Ph3P)(2)Os (9b), (eta(5)- C5H5)(dppf)Ru (9c)) have been synthesized from (HC C)(2)bfc (4) with either (Ph3P)AuCl (5) in the presence of HNEt2/[CuI] (synthesis of 6) or LnMX (LnMX = (eta(5) -C5H5)(Ph3P)(2)RuCl (7a); (eta(5)- C5H5)(Ph3P)(2)OsBr (7b); (eta(5)-C5H5)(dppf)RuCl (7c)) together with [H4N]PF6 and KOtBu (synthesis of 8 and 9), respectively. The structures of 6, 8b, 9a, 9b, and 9c in the solid state were determined by single-crystal X-ray structure analysis, showing unsymmetrical (8) or symmetrical geometries (6, 9), with almost eclipsed conformations or approximately midway positions between the fully eclipsed and the fully staggered conformation of the bfc cyclopentadienyl rings and with anti geometry of the linear ethynyl connecting units. UV-vis and NIR spectroscopic measurements suggest a weak interaction between the appropriate metal atoms. The associated radical cations were in situ generated by stepwise chemical oxidation and characterized by continuous wave electron paramagnetic resonance (EPR) investigations in X-band performed at low temperature.
A series of organometallic mono- and disubstituted bis(alkynyl)biferrocenes of type (LnMCC)(HCC)bfc (LnM = (η5-C5H5)(Ph3P)2Ru (8a), (η5-C5H5)(Ph3P)2Os (8b), (η5-C5H5)(dppf)Ru (8c); bfc = 1′,1′′′-biferrocenyl, ((η5-C5H4)2Fe)2; dppf = 1,1′-bis(diphenyl)phosphanyl ferrocene, (η5-C5H4PPh2)2Fe) and (LnMCC)2bfc (LnM = (Ph3P)Au (6), (η5-C5H5)(Ph3P)2Ru (9a), (η5-C5H5)(Ph3P)2Os (9b), (η5-C5H5)(dppf)Ru (9c)) have been synthesized from (HCC)2bfc (4) with either (Ph3P)AuCl (5) in the presence of HNEt2/[CuI] (synthesis of 6) or LnMX (LnMX = (η5-C5H5)(Ph3P)2RuCl (7a); (η5-C5H5)(Ph3P)2OsBr (7b); (η5-C5H5)(dppf)RuCl (7c)) together with [H4N]PF6 and KOtBu (synthesis of 8 and 9), respectively. The structures of 6, 8b, 9a, 9b, and 9c in the solid state were determined by single-crystal X-ray structure analysis, showing unsymmetrical (8) or symmetrical geometries (6, 9), with almost eclipsed conformations or approximately midway positions between the fully eclipsed and the fully staggered conformation of the bfc cyclopentadienyl rings and with anti geometry of the linear ethynyl connecting units. UV−vis and NIR spectroscopic measurements suggest a weak interaction between the appropriate metal atoms. The associated radical cations were in situ generated by stepwise chemical oxidation and characterized by continuous wave electron paramagnetic resonance (EPR) investigations in X-band performed at low temperature.
Author Lohan, Manja
Lapinte, Claude
Ecorchard, Petra
Rüffer, Tobias
Justaud, Frédéric
Lang, Heinrich
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  surname: Lohan
  fullname: Lohan, Manja
– sequence: 2
  givenname: Petra
  surname: Ecorchard
  fullname: Ecorchard, Petra
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  givenname: Tobias
  surname: Rüffer
  fullname: Rüffer, Tobias
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  givenname: Frédéric
  surname: Justaud
  fullname: Justaud, Frédéric
– sequence: 5
  givenname: Claude
  surname: Lapinte
  fullname: Lapinte, Claude
  email: heinrich.lang@chemie.tu-chemnitz.de, claude.lapinte@univ-rennes1.fr
– sequence: 6
  givenname: Heinrich
  surname: Lang
  fullname: Lang, Heinrich
  email: heinrich.lang@chemie.tu-chemnitz.de, claude.lapinte@univ-rennes1.fr
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Keywords ACTIVE FERROCENYL SPACER
TRANSITION-METAL-COMPLEXES
INTRAMOLECULAR ELECTRON-TRANSFER
FE-57 MOSSBAUER CHARACTERISTICS
CRYSTAL-STRUCTURE
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Snippet A series of organometallic mono- and disubstituted bis(alkynyl)biferrocenes of type (LnMCC)(HCC)bfc (LnM = (η5-C5H5)(Ph3P)2Ru (8a), (η5-C5H5)(Ph3P)2Os (8b),...
A series of orgarrometallic mono- and disubstituted bis(alkynyl)biferrocenes of type (LnMC C)-(HC C)bfc (LnM = (eta(5)-C5H5)(Ph3P)(2)Ru (8a),...
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SubjectTerms Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
Title 1′,1′′′-Bis(ethynyl)biferrocene as a Linking Group for Gold, Ruthenium, and Osmium Fragments: Synthesis, Solid State Structures, and Electrochemical, UV−Vis, and EPR Spectroscopical Studies
URI http://dx.doi.org/10.1021/om8011344
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