Ferrocene-Containing Polymers. X. Isomeric Bis(ferrocenylmethyl)ferrocenes

Neuse, Eberhard W.; Quo, Edward; Howells, W. Glenn.

doi:10.1021/jo01023a020

Cited by 14 publications

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“…These results indicate that addition‐condensation polymerization reaction of ferrocene and aldehydes forms 1,1′‐, 1,2‐, 1,3‐ferrocenylene units in the polymer backbone. The formation of similar isomers was also reported in formation of 12 , 12′ , and 12″ from the reaction of N , N ‐dimethylferrocene and ferrocene catalyzed by ZnCl 2 /HCl . Self‐condensation of ferrocenemethanol ( 13 ) catalyzed by HCl was reported to yield poly(ferrocenylene methylene) at higher temperature (95 °C) .…”

Section: Resultsmentioning

confidence: 76%

“…The formation of similar isomers was also reported in formation of 12, 12 0 , and 12 00 from the reaction of N,N-dimethylferrocene and ferrocene catalyzed by ZnCl 2 /HCl. 26 Self-condensation of ferrocenemethanol (13) catalyzed by HCl was reported to yield poly(ferrocenylene methylene) at higher temperature (95 C). 27 The reaction of 14) undergoes self-condensation polymerization in the presence of BF 3 Et 2 O to yield both linear polymer 8a n and cyclic oligomer 9a n (eq 5).…”

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confidence: 99%

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Cyclic and linear poly(ferrocenylene alkylene)s synthesized from addition‐condensation polymerization of ferrocene with aldehydes

Suzaki

Yoshigoe

Osakada

2013

J. Polym. Sci. Part A: Polym. Chem.

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Oligo‐ and poly(ferrocenylene alkylene)s, [Fe(C5H5‐x)(C5H5‐y)CHR]n (x = y = 1 or x = 2, y = 0; R = alkyl, aryl), were synthesized by Lewis acid‐promoted addition‐condensation polymerization of ferrocene with aldehydes. The reaction of alkyl aldehydes, such as n‐hept‐CHO, EtCHO and nBuCHO, with ferrocene yields a mixture of the cyclic and linear poly(ferrocenylene alkylene)s, while aryl aldehyde, such as C6F5CHO, CF3C6H4‐4‐CHO and MeC6H4‐4‐CHO, forms the linear polymers exclusively. The linear polymer has terminal Fe(C5H4)(C5H5) and CH2Aryl groups, which are characterized by high resolution mass spectroscopy. Results of addition‐condensation polymerization of ferrocenemethanol catalyzed by BF3 indicate that the propagating polymer of the above addition‐condensation polymerization contains terminal 1‐hydroxyalkyl‐ferrocenylene group, Fe(C5H4)[C5H4{CH(OH)R}]. The trimer prepared from ferrocene and paraformaldehyde dimethylacetal contains 1,1′‐, 1,2‐, and 1,3‐ferrocenylene units, suggesting that the polymers obtained from alkyl and aryl aldehydes are also composed of these structural units. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3627–3635

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Section: Resultsmentioning

confidence: 76%

mentioning

confidence: 99%

Cyclic and linear poly(ferrocenylene alkylene)s synthesized from addition‐condensation polymerization of ferrocene with aldehydes

Suzaki

Yoshigoe

Osakada

2013

J. Polym. Sci. Part A: Polym. Chem.

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“…In 1962 the reaction of 6-ferrocenylfulvene and lithium aluminum hydride, followed by addition of iron(II) chloride, to afford the CH 2 bridged species (FcCH 2 C 5 H 4 ) 2 Fe was reported . The same species was later isolated by Neuse, Quo, and Howells from a mixture of products arising from the reaction of [( N , N -dimethylamino)methyl]ferrocene and ferrocene in the presence of zinc chloride and hydrochloric acid . Barr, Lentzner, and Watts also synthesized (FcCH 2 C 5 H 4 ) 2 Fe, by reduction of the diketone (FcCOC 5 H 4 ) 2 Fe with lithium aluminum hydride in the presence of aluminum chloride.…”

Section: Metallocenes Linked By Carbon Bridges (Excluding Fused-ring ...mentioning

confidence: 97%

“…150 The same species was later isolated by Neuse, Quo, and Howells from a mixture of products arising from the reaction of [(N,N-dimethylamino)methyl]ferrocene and ferrocene in the presence of zinc chloride and hydrochloric acid. 151 Barr, Lentzner, and Watts also synthesized (FcCH 2 C 5 H 4 ) 2 Fe, by reduction of the diketone (FcCOC 5 H 4 ) 2 Fe with lithium aluminum hydride in the presence of aluminum chloride. The diketone itself was one of many products isolated from the reaction of 1,1′-bis(chlorocarbonyl)ferrocene, ferrocene, and aluminum chloride.…”

Section: Metallocenes Linked By Saturated Carbon Bridgesmentioning

confidence: 99%

Metal−Metal Interactions in Linked Metallocenes

1997

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References 665 Dermot O'Hare was born and educated in Newry, Co Down, N. Ireland. He received his B.A. in 1982 at Balliol College, Oxford, and subsequently remained there to carry out his D.Phil. under the supervision of Professor M. L. H. Green FRS. In 1985 he was awarded a Royal Commission of 1851 Research Fellowship. In 1986−87 he spent one year at the CR&D Laboratories of E.I. duPont de Nemours in Wilmington, DE, working with Professor J. S. Miller. He is currently a University Lecturer in Inorganic Chemistry and a Septcentenary Fellow of Balliol College, Oxford. He has published research articles on a wide range of topics from synthetic molecular organometallic chemistry to time-resolved, in situ synchrotron X-ray diffraction. In 1993 he co-authored with Professor D. W. Bruce the book entitled Inorganic Materials, which has just appeared as a 2nd edition. In 1996 he was awarded the Royal Society of Chemistry's Sir Edward Frankland Fellowship.

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“…The incorporation of ferrocene into the polymer’s backbone led to novel electrochemical properties, such as pronounced electron-donating ability, fast electrochemical response, thermal stability, and redox reversibility, and thus a wide range of applications became accessible. ,− The group of Manners introduced ferrocenyl units into polymeric materials by thermal ring-opening polymerization (ROP) of strained silicon-bridged feroccenophanes to form high molar mass organometallic polymers . Furthermore, polymers with various bridging moieties such as boron, sulfur, silicon, CH 2 , and C 2 H 4 in the main chains of ferrocene-containing polymer backbones have been developed. , However, the backbone moieties of those polymers often lack conjugation, which hinders backbone-mediated electron transport throughout the polymer …”

Section: Introductionmentioning

confidence: 99%

Electron Transfer Studies on Conjugated Ferrocenyl-Containing Oligomers

et al. 2016

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1,2-Divinylferrocene (1) and 1,2-diformylferrocene (3) have been converted to ferrocenyl-containing oligomers in good yields using ADMET (acyclic diene metathesis) and HWE (Horner–Wadsworth–Emmons) reaction protocols. The resulting oligomers showed a high uniformity (low dispersity values); however, the poor solubility limits the chain growth and led to low average molecular weights. Within electrochemical measurements (CV) the conjugated materials showed reversible behavior that was stable during multicyclic experiments. Coupled electrochemical and spectroscopic studies confirmed electron transfer interactions between the ferrocenyl units through the oligomeric chains.

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Ferrocene-Containing Polymers. X. Isomeric Bis(ferrocenylmethyl)ferrocenes

Cited by 14 publications

References 1 publication

Cyclic and linear poly(ferrocenylene alkylene)s synthesized from addition‐condensation polymerization of ferrocene with aldehydes

Cyclic and linear poly(ferrocenylene alkylene)s synthesized from addition‐condensation polymerization of ferrocene with aldehydes

Metal−Metal Interactions in Linked Metallocenes

Electron Transfer Studies on Conjugated Ferrocenyl-Containing Oligomers

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