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User:Barras/Ferrocene
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(contracted; show full)t5=J.|last6=Dive|first6=D.|title=The antimalarial ferroquine: from bench to clinic|journal=Parasite|volume=18|issue=3|year=2011|pages=207–214|issn=1252-607X|doi=10.1051/parasite/2011183207|url=http://www.parasite-journal.org/articles/parasite/full_html/2011/03/parasite2011183p207/parasite2011183p207.html|PMID=21894260|PMC=3671469}} {{open access}}</ref><ref>Roux, C.; Biot, C., "Ferrocene-based antimalarials", Future Med. Chem. 2012, 4, 783-797. {{DOI|10.4155/fmc.12.26}}</ref> 


===Materials chemistry===
[[File:Wettability of a silica surface with a bound ferrocene-substituted polymer.jpg|left|thumb|500px|Strands of an uncharged ferrocene-substituted polymer are tethered to a [[hydrophobic]] [[silica]] surface.  Oxidation of the ferrocenyl groups produces a [[hydrophilic]] surface due to electrostatic attractions between the resulting charges and the polar solvent.<ref name = Pietschnig />]] 
Ferrocene, being readily decomposed to iron nanoparticles, can be used as a catalyst for the production of carbon nanotubes.<ref>{{cite journal|first1=Devin |last1=Conroya |first2=Anna |last2=Moisalab|first3= Silvana |last3=Cardosoa |first4=Alan |last4=Windleb |first5=John |last5=Davidson|journal=[[Chemical Engineering Science|Chem. Eng. Sci.]]|year=2010|volume=65|pages=2965–2977|doi=10.1016/j.ces.2010.01.019|title=Carbon nanotube reactor: Ferrocene decomposition, iron particle growth, nanotube aggregation and scale-up|issue=10}}</ref> The [[vinyl]]<nowiki></nowiki>ferrocene from ferrocene can be made by a [[Wittig reaction]] of the [[aldehyde]], a [[phosphonium salt]] and [[sodium hydroxide]].<ref>{{cite journal|last1=Liu |first1=Wan-yi |last2=Xu |first2=Qi-hai|last3= Ma|first3= Yong-xiang|last4= Liang|first4= Yong-min|last5= Dong|first5= Ning-li|last6= Guan|first6= De-peng|journal=[[Journal of Organometallic Chemistry|J. Organomet. Chem.]]|year=2001|volume=625|pages=128–132|doi=10.1016/S0022-328X(00)00927-X|title=Solvent-free synthesis of ferrocenylethene derivatives}}</ref> The vinyl ferrocene can be converted into a polymer (polyvinylferrocene, PVFc) which can be thought of as a ferrocenyl version of [[polystyrene]] (the phenyl groups are replaced with ferrocenyl groups). Another polymer which can be formed is poly(2-(methacryloyloxy)ethyl ferrocenecarboxylate), PFcMA.  In addition to using organic polymer backbones, these pendant ferrocene units have been attached to inorganic backbones such as [[polysiloxane]]s, [[polyphosphazene]]s, and poly[[phosphinoborane]]s, (&ndash;PH(R)&ndash;BH<sub>2</sub>&ndash;)<sub>''n''</sub>, and the resulting materials exhibit unusual physical and electronic properties relating to the ferrocene / ferrocinium redox couple.<ref name = Pietschnig>{{cite journal|first = Rudolf|last = Pietschnig|title = Polymers with pendant ferrocenes|journal = [[Chemical Society Reviews|Chem. Soc. Rev.]]|year = 2016|volume = 45|pages = 5216-5231|doi = 10.1039/C6CS00196C}}</ref>  Both PVFc and PFcMA have been tethered onto [[silica]] wafers and the [[wettability]] measured when the polymer chains are uncharged and when the ferrocene moieties are oxidised to produce positively charged groups.  The [[contact angle]] with water on the PFcMA-coated wafers was 70&deg; smaller following oxidation, while in the case of PVFc the decrease was 30&deg;, and the switching of wettability is reversible.  In the PFcMA case, the effect of lengthening the chains and hence introducing more ferrocene groups is significantly larger reductions in the contact angle upon oxidation.<ref name = Pietschnig /><ref>{{cite journal|first1 = J.|last1 = Elbert|first2 = M.|last2 = Gallei|first3 = C.|last3 = Rüttiger|first4 = A.|last4 = Brunsen|first5 = H.|last5 = Didzoleit|first6 = B.|last6 = Stühn|first7 = M.|last7 = Rehahn|journal = [[Organometallics]]|year = 2013|volume = 32|issue = 20|pages = 5873–5878|title = Ferrocene Polymers for Switchable Surface Wettability|doi = 10.1021/om400468p}}</ref>⏎
⏎
===As a ligand scaffold===
Chiral ferrocenyl [[phosphine]]s are employed as ligands for transition-metal catalyzed reactions. Some of them have found industrial applications in the synthesis of pharmaceuticals and agrochemicals. For example, the [[diphosphines|diphosphine]] [[1,1'-bis(diphenylphosphino)ferrocene|1,1′-bis(diphenylphosphino)ferrocene]] (dppf) is a valuable ligand for [[palladium]]-[[coupling reaction]]s.

==Derivatives and variations==
(contracted; show full)
:[[Image:Hexaferrocenylbenzene.png|400px|Hexaferrocenylbenzene synthesis by Negishi coupling]]
The [[yield (chemistry)|yield]] is only 4%, which is further evidence consistent with substantial [[steric strain|steric]] crowding around the arene core.
{{clear}}


⏎
===Materials chemistry===
[[File:Wettability of a silica surface with a bound ferrocene-substituted polymer.jpg|left|thumb|500px|Strands of an uncharged ferrocene-substituted polymer are tethered to a [[hydrophobic]] [[silica]] surface.  Oxidation of the ferrocenyl groups produces a [[hydrophilic]] surface due to electrostatic attractions between the resulting charges and the polar solvent.<ref name = Pietschnig />]] 
Ferrocene, a precursor to iron nanoparticles, can be used as a catalyst for the production of carbon nanotubes.<ref>{{cite journal|first1=Devin |last1=Conroya |first2=Anna |last2=Moisalab|first3= Silvana |last3=Cardosoa |first4=Alan |last4=Windleb |first5=John |last5=Davidson|journal=[[Chemical Engineering Science|Chem. Eng. Sci.]]|year=2010|volume=65|pages=2965–2977|doi=10.1016/j.ces.2010.01.019|title=Carbon nanotube reactor: Ferrocene decomposition, iron particle growth, nanotube aggregation and scale-up|issue=10}}</ref> The [[vinyl]]<nowiki></nowiki>ferrocene from ferrocene can be made by a [[Wittig reaction]] of the [[aldehyde]], a [[phosphonium salt]] and [[sodium hydroxide]].<ref>{{cite journal|last1=Liu |first1=Wan-yi |last2=Xu |first2=Qi-hai|last3= Ma|first3= Yong-xiang|last4= Liang|first4= Yong-min|last5= Dong|first5= Ning-li|last6= Guan|first6= De-peng|journal=[[Journal of Organometallic Chemistry|J. Organomet. Chem.]]|year=2001|volume=625|pages=128–132|doi=10.1016/S0022-328X(00)00927-X|title=Solvent-free synthesis of ferrocenylethene derivatives}}</ref> The vinyl ferrocene can be converted into a polymer (polyvinylferrocene, PVFc), a ferrocenyl version of [[polystyrene]] (the phenyl groups are replaced with ferrocenyl groups). Another polymer which can be formed is poly(2-(methacryloyloxy)ethyl ferrocenecarboxylate), PFcMA.  In addition to using organic polymer backbones, these pendant ferrocene units have been attached to inorganic backbones such as [[polysiloxane]]s, [[polyphosphazene]]s, and poly[[phosphinoborane]]s, (&ndash;PH(R)&ndash;BH<sub>2</sub>&ndash;)<sub>''n''</sub>, and the resulting materials exhibit unusual physical and electronic properties relating to the ferrocene / ferrocinium redox couple.<ref name = Pietschnig>{{cite journal|first = Rudolf|last = Pietschnig|title = Polymers with pendant ferrocenes|journal = [[Chemical Society Reviews|Chem. Soc. Rev.]]|year = 2016|volume = 45|pages = 5216-5231|doi = 10.1039/C6CS00196C}}</ref>  Both PVFc and PFcMA have been tethered onto [[silica]] wafers and the [[wettability]] measured when the polymer chains are uncharged and when the ferrocene moieties are oxidised to produce positively charged groups.  The [[contact angle]] with water on the PFcMA-coated wafers was 70&deg; smaller following oxidation, while in the case of PVFc the decrease was 30&deg;, and the switching of wettability is reversible.  In the PFcMA case, the effect of lengthening the chains and hence introducing more ferrocene groups is significantly larger reductions in the contact angle upon oxidation.<ref name = Pietschnig /><ref>{{cite journal|first1 = J.|last1 = Elbert|first2 = M.|last2 = Gallei|first3 = C.|last3 = Rüttiger|first4 = A.|last4 = Brunsen|first5 = H.|last5 = Didzoleit|first6 = B.|last6 = Stühn|first7 = M.|last7 = Rehahn|journal = [[Organometallics]]|year = 2013|volume = 32|issue = 20|pages = 5873–5878|title = Ferrocene Polymers for Switchable Surface Wettability|doi = 10.1021/om400468p}}</ref>⏎
==See also==
* [[Josiphos ligands]]

==References==
{{reflist|30em}}

==External links==
* [http://www.periodicvideos.com/videos/mv_ferrocene.htm Ferrocene] at ''[[The Periodic Table of Videos]]'' (University of Nottingham)
* [http://www.cdc.gov/niosh/npg/npgd0205.html NIOSH Pocket Guide to Chemical Hazards] (Centers for Disease Control and Prevention)

{{commons category|ferrocene}}

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[[Category:Organoiron compounds]]
[[Category:Metallocenes]]
[[Category:Antiknock agents]]
[[Category:Sandwich compounds]]
[[Category:Cyclopentadienyl complexes]]