ROMP of t-butyl-substituted ferrocenophanes affords soluble conjugated polymers that contain ferrocene moieties in the backbone

Heo, Richard W.; Park, Joon-Seo; Goodson, Jason T.; Claudio, Gil C.; Takenaga, Mitsuru; Albright, Thomas A.; Lee, T. Randall

doi:10.1016/j.tet.2004.06.067

Cited by 48 publications

(46 citation statements)

References 59 publications

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“…Mononuclear [n]ferrocenophanes with n > 2 [33] and multinuclear [m.m]metallocenophanes [34] are essentially unstrained although some containing olefinic bridges are appropriate candidates for ring-opening metathesis polymerization (ROMP). [35][36][37][38][39] Propane-bridged [3]ferrocenophanes can be synthesized with tilt angles up to 12.68 (Table 2), [33,[40][41][42][43] although photoelectron spectroscopy reveals more similarity between the electronic structure of these compounds and nonbridged analogues than with more highly strained ferrocenophanes. [44] Carbonbridged [2]ferrocenophanes with saturated (e.g.…”

Section: Group 14 Elements As Bridges Carbonmentioning

confidence: 99%

Strained Metallocenophanes and Related Organometallic Rings Containing π‐Hydrocarbon Ligands and Transition‐Metal Centers

2007

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The structures, bonding, and ring-opening reactions of strained cyclic carbon-based molecules form a key component of standard textbooks. In contrast, the study of strained organometallic molecules containing transition metals is a much more recent development. A wealth of recent research has revealed fascinating nuances in terms of structure, bonding, and reactivity. Building on initial work on strained ferrocenophanes, a broad range of strained organometallic rings composed of a variety of different metals, pi-hydrocarbon ligands, and bridging elements has now been developed. Such strained species can potentially undergo ring-opening reactions to functionalize surfaces and ring-opening polymerization to form easily processed metallopolymers with properties determined by the presence of the metal and spacer. This Review summarizes the current state of knowledge on the preparation, structural characterization, electronic structure, and reactivity of strained organometallic rings with pi-hydrocarbon ligands and d-block metals.

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Section: Group 14 Elements As Bridges Carbonmentioning

confidence: 99%

Strained Metallocenophanes and Related Organometallic Rings Containing π‐Hydrocarbon Ligands and Transition‐Metal Centers

2007

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“…The addition of bulky and flexible groups is often used to increase solubility of macromolecules. [14] The reagents 1-4 were prepared by using known coupling procedures and they were indeed found to have sufficient solubility in solvents such as acetone or dichloromethane to allow easy manipulation and characterization (see experimental section). To further enhance the solubility of the coordinated organoplatinum(IV) complex, the ligand bu 2 bipy was used as the supporting ligand in the reagent [PtMe 2 (bu 2 bipy)]; 5, instead of the parent 2,2Ј-bipyridine.…”

Section: Resultsmentioning

confidence: 99%

Organoplatinum(IV) Complexes with Amide Groups: Supramolecular Structure as a Function of Ligand Flexibility

Au¹,

Jennings²,

Puddephatt³

2009

Eur J Inorg Chem

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The oxidative addition of the benzyl bromide derivative 4‐BrCH2C6H4(CH2)xC(=O)NH(CH2)y‐4‐C6H4‐tBu (A), x = y = 0; (B), x = 0, y = 1; (C), x = 1, y = 0; (D), x = y = 1, to the dimethylplatinum(II) complex [PtMe2(bu2bipy)] (1), bu2bipy = 4,4′‐di‐tert‐butyl‐2,2′‐bipyridine, gave the corresponding amide‐substituted benzylplatinum(IV) complexes of the formula [PtBrMe2(4‐CH2C6H4(CH2)xC(=O)NH(CH2)y‐4‐C6H4‐tBu)(bu2bipy)], bu2bipy = 4,4′‐di‐tert‐butyl‐2,2′‐bipyridine, 2–5. In the solid state, the complexes 2–5 undergo self‐assembly to give the supramolecular polymers 2–4 or the dimers 5. Intermolecular N–H···Br‐Pt hydrogen bonds are favored over the typical NH···O=C hydrogen bonds found in organic amides. The carbonyl group may be hydrogen‐bonded to solvent or not involved in hydrogen bonding. The structures are dependent on the size and flexibility of the amide‐substituted benzyl group. In solution, the complexes 3–5 exhibited an equilibrium between the neutral complexes and the bromo‐bridged, ionic binuclear complexes [(μ‐Br){PtBrMe2(4‐CH2C6H4(CH2)xC(=O)NH(CH2)y‐4‐C6H4‐tBu)(bu2bipy)}2]Br. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…Lee et al conducted several structural modifications [22e24] on the 1,3-butadienyl bridging unit of the parent compound 2, first synthesized by Pudelski and Callstrom through a heteroannular cyclization reaction under basic condition (aqueous KOH in methanol) [25,26]. All of the resulting [4]ferrocenophanes were "1-monosubstituted", bearing an alkyl (t-butyl) [22,23] or aryl (phenyl or mesityl) [24] group at the 1-position of the 1,3-butadienyl bridging unit (see 3, 4 and 5 in Chart 1). ROMP of these monomers afforded soluble polymeric materials with high molecular weight.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the first 1,3-disubstituted 1,3-butadienyl heteroannular bridged [4]ferrocenophane

Xie

Zhang

et al. 2011

Journal of Organometallic Chemistry

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ROMP of t-butyl-substituted ferrocenophanes affords soluble conjugated polymers that contain ferrocene moieties in the backbone

Cited by 48 publications

References 59 publications

Strained Metallocenophanes and Related Organometallic Rings Containing π‐Hydrocarbon Ligands and Transition‐Metal Centers

Strained Metallocenophanes and Related Organometallic Rings Containing π‐Hydrocarbon Ligands and Transition‐Metal Centers

Organoplatinum(IV) Complexes with Amide Groups: Supramolecular Structure as a Function of Ligand Flexibility

Synthesis of the first 1,3-disubstituted 1,3-butadienyl heteroannular bridged [4]ferrocenophane

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