Polymerization of 4-(ferrocenylethynyl)phenylacetylene with transition metal catalysts

Sedláček, Jan; Vohlı́dal, Jiřı́; Patev, Nikolay; Pacovská, Marta; Cabioch, Sandrine; Lavastre, Olivier; Dixneuf, Pierre H.; Balcar, Hynek; Matějka, Pavel

doi:10.1002/(sici)1521-3935(19990501)200:5<972::aid-macp972>3.0.co;2-h

Cited by 21 publications

(9 citation statements)

References 22 publications

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“…Later, the MW stability in air was being occasionally reported in some studies dealing preferentially with other aspects of substituted polyacetylenes 27, 40, 48–53. In 1990s, our group published several articles devoted exclusively to the degradation of monosubstituted high‐MW polyarylacetylenes (mostly of cis / trans microstructure)54–57 and also proved size exclusion chromatography (SEC) as a powerful tool for the study of this phenomenon 57–62. Our results together with those of systematic studies of other research groups63–66 can be summarized as follows: (i) The degradation is either conditioned or at least strongly accelerated by the presence of oxygen in the system, and in deeply degrading polyacetylenes the oxidized fragments of polymer chains are usually found.…”

Section: Introductionmentioning

confidence: 52%

“…These, we denote as “high‐ cis ” polyacetylenes in this article. On the other hand, W‐ and Mo‐based catalysts, which operate in the metathesis propagation mode, generally give nonstereoregular “ cis / trans ” polyacetylenes 38–46. Usually, the stereoregularity decreases according to the catalyst applied in the following order: Rh ≫ Mo > W.…”

Section: Introductionmentioning

confidence: 99%

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Molecular weight and configurational stability of poly[(fluorophenyl)acetylene]s prepared with metathesis and insertion catalysts

Bondarev

Zednı́k

Plutnarová

et al. 2010

J. Polym. Sci. A Polym. Chem.

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Series of high-cis and cis/trans poly[(fluorophenyl) acetylene]s (PFPhA) have been prepared by polymerization of (2-fluorophenyl)acetylene, (3-fluorophenyl)acetylene, and (4fluorophenyl)acetylene with catalysts: [Rh(1,5-cyclooctadiene) OCH 3 ] 2 (high-cis PFPhAs) and tungsten(VI) oxychloride/tetraphenyltin (cis/trans PFPhAs). The molecular weight and configurational stability under various conditions at room temperature were studied for both PFPhAs series by means of size exclusion chromatography, 1 H-NMR, and UV-vis techniques. All samples exhibited slow degradation when exposed to the atmosphere in the solid state; the rate of degradation was independent on the F-position on the Ph ring. The rate of degradation increased up to three orders of magnitude in the tetrahydrofuran solution where it was higher for high-cis polymers compared with their cis/trans counterparts. The degradation of high-cis PFPhAs was accompanied by significant cis-to-trans isomerization in aerated tetrahydrofuran solution. Rate of degradation and isomerization exhibited the same dependence on the F-position on the Ph ring. The hypothesis was postulated that the degradation of high-cis PFPhAs in solution was accelerated by cis-to-trans isomerization due to which the content of unpaired electrons on the main chains is enhanced. In both high-cis and cis/trans series of polymers the ortho-substituted isomers exhibited an enhanced stability compared with metaand para-substituted isomers.

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Section: Introductionmentioning

confidence: 52%

Section: Introductionmentioning

confidence: 99%

Molecular weight and configurational stability of poly[(fluorophenyl)acetylene]s prepared with metathesis and insertion catalysts

Bondarev

Zednı́k

Plutnarová

et al. 2010

J. Polym. Sci. A Polym. Chem.

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“…Methods of coordination polymerization applying either metathesis catalysts (Mo and W based)28–32 or insertion catalysts (Rh based)24–26, 33–36 are used for the preparation of these polymers. The choice of catalyst allows the configurational structure of poly(monosubstituted acetylene)s to be controlled, particularly the cis double bond content, which increases according to the catalyst applied in the order W < Mo < Rh 24, 29, 34, 37–39. Despite unquestionable progress in the chemistry of poly(monosubstituted acetylene)s, these promising materials still suffer from limited stability 40–46…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Spectral Properties of Novel Poly(disubstituted acetylene)s

Duchoslavová

Sivkova

Hanková

et al. 2011

Macro Chemistry & Physics

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The synthesis of mostly new acetylenes, R1CCR2, (R1 = 4‐t‐butylphenyl; R2 = 4‐t‐butylphenyl; 4‐[(t‐butyl)(diphenyl)silyloxy]phenyl; 1‐naphthyl; 2‐naphthyl; 9‐anthryl) is reported. Their UV‐vis characteristics are discussed in comparison to the results of TD‐DFT calculations. R1CCR2 (except for R2 = 9‐anthryl) give polyacetylenic polymers—[C(R1) = C(R2)]‐n, insoluble if R1 = R2 and well soluble if R1 ≠ R2 in polymerization with TaCl5/SnBu4. Polymerizability increases with increasing monomer triple bond accessibility for the catalyst. The photoluminescence yield of the soluble polymers rises in the R2 order: 1‐naphthyl < 2‐naphthyl < 4‐[(t‐butyl)(diphenyl)silyloxy]phenyl.

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“…Surprisingly, very few polyacetylenes with pendant metal complexes have been described. Among them, the most studied are poly(ethynylferrocene) or poly(ethynylrutenocene) 19–28. Other metallopolyacetylenes reported are poly(phenylacetylene)s bearing Zn phorphirine29 or Ru tris(imine)30 complexes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and luminescence of poly(phenylacetylene)s with pendant iridium complexes and carbazole groups

Vicente¹,

Gil‐Rubio²,

Zhou³

et al. 2010

J. Polym. Sci. A Polym. Chem.

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Poly(phenylacetylene)s containing pendant phosphorescent iridium complexes have been synthesized and their electrochemical, photo-and electroluminescent properties studied. The polymers have been synthesized by rhodium-catalyzed copolymerization of 9-(4-ethynylphenyl)carbazole (CzPA) and phenylacetylenes (C^N) 2 Ir(j). In addition, organic poly(phenylacetylene)s with pendant carbazole groups have been synthesized by rhodium-catalyzed copolymerization of CzPA and 1-ethynyl-4-pentylbenzene. Complex (C^N) 2 Ir(j 2 -O,O 0 -MeC(O)CHC(O)Ph) (Ir piq Ph; C^N ¼ 2-(isoquinolin-1-yl)phenyl-j 2 -N,C 1 ) was prepared and characterized. While the copolymers of the Ir ppy series were weakly phosphorescent, those of the Ir piq series displayed at room temperature intense emissions from the carbazole (fluorescence) and iridium (phosphorescence) emitters, being the latter dominant when the spectra were recorded using polymer films. Triple layer OLED devices employing copolymers of the Ir piq series or the model complex Ir piq Ph yielded electroluminescence with an emission spectra originating from the iridium complex and maximum external quantum efficiencies of 0.46% and 2.99%, respectively.

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Polymerization of 4-(ferrocenylethynyl)phenylacetylene with transition metal catalysts

Cited by 21 publications

References 22 publications

Molecular weight and configurational stability of poly[(fluorophenyl)acetylene]s prepared with metathesis and insertion catalysts

Molecular weight and configurational stability of poly[(fluorophenyl)acetylene]s prepared with metathesis and insertion catalysts

Synthesis and Spectral Properties of Novel Poly(disubstituted acetylene)s

Synthesis and luminescence of poly(phenylacetylene)s with pendant iridium complexes and carbazole groups

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