Soluble, highly conjugated derivatives of polyacetylene from the ring-opening metathesis polymerization of monosubstituted cyclooctatetraenes: synthesis and the relationship between polymer structure and physical properties

Gorman, Christopher B.; Ginsburg, Eric J.; Grubbs, Robert H.

doi:10.1021/ja00057a024

Cited by 122 publications

(101 citation statements)

References 19 publications

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“…44 Similarly, substituted polyacetylenes produced from the ROMP of monosubstituted cyclooctatetraenes are soluble in organic solvents when the substituents consist of bulky alkyl groups. 39 Furthermore, the incorporation of polar functional groups has permitted the synthesis of water-soluble versions of polythiophene 40 and polyaniline. 41 When we initially undertook this strategy, we believed that the ROMP of bridge-alkylated derivatives would afford readily soluble versions of polymer.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2004

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Section: Introductionmentioning

confidence: 99%

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

et al. 2004

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“…It is well-known that the solubility of polyacetylene decreases steadily with the chain growth of the oligomer. 15 As the reaction mixtures could not be investigated in one pot because of the precipitation, the components were hydrogenated off to obtain fully soluble, saturated -phenyl substituted hydrocarbon chains. Then, assuming that the components of the reaction mixture retain comparative response factors, GC-MS analyses were carried out and the approximate values of the conversion and yields were estimated from the peak areas of the total ion current (TIC) chromatograms.…”

Section: Synthesis Of Polyene Homologsmentioning

confidence: 99%

Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species

Kovács

Sághy

Turczel

et al. 2017

Journal of Organometallic Chemistry

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Cross-metathesis (CM) of conjugated polyenes, such as 1,6-diphenyl-1,3,5-hexatriene (1) and α-eleostearic acid methyl ester (2) with several olefins, including 1-hexene, dimethyl maleate and cis-stilbene as model compounds has been carried out using (1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-dichloro(o-isopropoxyphenylmethylene)ruthenium (Hoveyda-Grubbs 2 nd generation, HG2) catalyst. The feasibility of these reactions is demonstrated by the observed high conversions and reasonable yields. Thus, regardless of the relatively low electron density, =CH-CH= conjugated units of molecules, including compound 2 as a sustainable, non-foodstuff source, can be utilized as building blocks for the synthesis of various value-added chemicals via olefin metathesis. DFT-studies and the product spectrum of the self-metathesis of 1,6-diphenyl-1,3,5-hexatriene suggest that a Ru   -allylidene complex is the active species in the reaction.

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“…One common method is to attach substituents along the polymer backbone. 14,17,18 Another synthetic method used is to produce copolymers by introducing a second monomer with good solubility properties. 14,16,19,20 In the second approach, block copolymer composition is limited because both monomers must be polymerizable by the same method.…”

mentioning

confidence: 99%

Electro-Induced Early Transition Metal Metathesis Catalyst Systems for the Production of Polyacetylene

Karabulut

2009

Polym. J.

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The use of electro-induced Mo and W-based catalysts has been investigated in the ring opening metathesis polymerization (ROMP) of 1,3,5,7-cyclooctatetraene (COT). The soluble and conjugated polyacetylene (PA) was obtained under ambient temperature and pressure without employing any secondary reagent (comonomer, chain transfer agent) or substituted monomer (R-COT). NMR analysis results show that the electrochemical Mo-based system leads to a completely (100%) trans product, however, mainly (80%) trans polymer was obtained with W-based analogue for PA.KEY WORDS: Ring Opening Metathesis Polymerization (ROMP) / 1,3,5,7-Cyclooctatetraene (COT) / Polyacetylene (PA) / Transition Metal Catalyst / Electrochemistry / Conjugated polymers, the simplest being polyacetylene, are of current interest because the substantial electronic delocalization along their backbones gives rise to interesting optical and nonlinear optical properties and allows them to become good electrical conductors. These properties might lead to a variety of applications including optical signal processing and information storage, lightweight substitutes for metals in batteries and materials for solar energy conversion.

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Soluble, highly conjugated derivatives of polyacetylene from the ring-opening metathesis polymerization of monosubstituted cyclooctatetraenes: synthesis and the relationship between polymer structure and physical properties

Cited by 122 publications

References 19 publications

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

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

Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species

Electro-Induced Early Transition Metal Metathesis Catalyst Systems for the Production of Polyacetylene

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