Low-oxidation-potential conducting polymers: Alternating substituted para-phenylene and 3,4-ethylenedioxythiophene repeat units

Irvin, Jennifer A.; Reynolds, John R.

doi:10.1016/s0032-3861(97)00496-5

Cited by 54 publications

(49 citation statements)

References 28 publications

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“…[23] Under atmospheric conditions, hydroquinone (100 g, 0.908 mol, 1.0 equiv) was added to an apparatus equipped with potassium hydroxide (ca. 0.02 M) trap to quench the HBr gas evolved from the reaction.…”

Section: Experimental Partmentioning

confidence: 99%

“…1 (2) This compound was synthesized in a manner analogous to that reported in the literature. [23] Dibromohydroquinone (70.0 g, 0.261 mol, 1.0 equiv) was dissolved in ethyl alcohol (200 ml). Potassium hydroxide (38.1 g, 0.679 mol, 2.6 equiv) was dissolved in deionized water (300 ml), added dropwise, and allowed to stir for 1 h. A solution of 1-bromopropane (120 ml, 1.31 mol, 5.0 equiv) in ethanol (100 ml) was prepared and added dropwise.…”

Section: Experimental Partmentioning

confidence: 99%

“…Hydroquinone was dibrominated to yield 2,5-dibromohydroquinone (1) following the literature. [23] Compound 1 was then alkylated using Williamson ether synthesis to yield the dialkoxy compound 2. [23] This can then be formylated using butyl lithium and DMF to form the dialdehylde 3.…”

Section: Rigid-rod Polymersmentioning

confidence: 99%

“…[23] Compound 1 was then alkylated using Williamson ether synthesis to yield the dialkoxy compound 2. [23] This can then be formylated using butyl lithium and DMF to form the dialdehylde 3. [24] Subsequent reaction using standard Wittig conditions yields 1,4-dipropoxy-2,5-divinylbenzene (4), which can be used in an ADMET polymerization.…”

Section: Rigid-rod Polymersmentioning

confidence: 99%

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Solid‐State Olefin Metathesis: ADMET of Rigid‐Rod Polymers and Ring‐Closing Metathesis

Oakley

Wagener

2004

Macro Chemistry & Physics

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Summary: Solid‐state olefin metathesis of rigid‐rod acyclic diene metathesis (ADMET) polymers and ring‐closing metathesis (RCM) have been investigated. 1,4‐Dipropoxy‐2,5‐divinylbenzene (4) was synthesized and used in a bulk ADMET polymerization to produce oligomers of dialkoxy poly(phenylene vinylene). The reaction was continued in the solid state, effectively doubling the molecular weight. Solid‐state RCM was investigated with a variety of solid dienes and metathesis catalysts, and demonstrated in low conversions using amide diene 5 with catalysts 9, 13, and 14. magnified image

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Section: Experimental Partmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%

Section: Rigid-rod Polymersmentioning

confidence: 99%

Section: Rigid-rod Polymersmentioning

confidence: 99%

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Solid‐State Olefin Metathesis: ADMET of Rigid‐Rod Polymers and Ring‐Closing Metathesis

Oakley

Wagener

2004

Macro Chemistry & Physics

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“…Thiophene, 3,4-ethylenedioxythiophene (EDOT) and their derivatives have mostly been used as the electron-donating moieties in constructing D-A-D architecture. Low oxidation potential of an electron-rich donor in the structure of monomer allows performing electrochemical polymerization at low potentials [12].…”

Section: Introductionmentioning

confidence: 99%

Molecular architecture: Another plausible pathway toward a low band gap polymer

Tarkuc

Udum

Toppare

2010

Journal of Electroanalytical Chemistry

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Chromogenic Materials, Electrochromic

Samat

Guglielmetti

2004

Kirk-Othmer Encyclopedia of Chemical Technology

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Electrochromism is a reversible color change in a material, often a thin film, that accompanies an oxidation–reduction reaction driven by a small current at low voltage. It occurs at or near room temperature in both cathodically colored and anodically colored inorganic and organic compounds. It is accompanied by ion insertion/extraction (doping/undoping) for charge balance in thin solid films. Electrochromic chromogenic materials are divided into two groups based on whether or not insertion/extraction occurs or does. For the smaller, noninsertion group , reversible coloration occurs in solution or is associated with reversible electrodeposition from solution. The best known members are viologens, polymers systems such as polyheterocycles, metallopolymers, metal phthalocyanines, and inorganic electrodeposition of silver halides. In the insertion/extraction group, three main categories of systems have been investigated: Cathodically colored inorganic materials usually color with either H + or alkali ion insertion. The best known film is amorphous tungsten oxide, in part, because of its relatively high coloration efficiency in the visible region. Anodically colored inorganic materials, including Prussian blue, also having a high coloration efficiency, and hydrated oxides of iridium and nickel. Often, K + is inserted for Prussian blue. There is a lively debate about whether H + or OH − is active for the hydrated oxides. Doped/undoped organic films color both anodically and cathodically in general. There is much less known about this type of electrochromism in literature which, as a whole, has been reviewed through 1990. Polyaniline, polypyrrole, polythiophene or tetrathiafulvalene systems with dopants as proton, alkaline metal or ClO 4 − , BF 4 − anions have been studied. A recent system concerns the preparation of electrochromic layers by using sol–gels formation controlling the variation of the viscosity of the electrolyte and polymer. Many potential applications are possible but some technical aspects have yet to be improved for a commercial availability.

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Low-oxidation-potential conducting polymers: Alternating substituted para-phenylene and 3,4-ethylenedioxythiophene repeat units

Cited by 54 publications

References 28 publications

Solid‐State Olefin Metathesis: ADMET of Rigid‐Rod Polymers and Ring‐Closing Metathesis

Solid‐State Olefin Metathesis: ADMET of Rigid‐Rod Polymers and Ring‐Closing Metathesis

Molecular architecture: Another plausible pathway toward a low band gap polymer

Chromogenic Materials, Electrochromic

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