Synthesis and characterization of poly[[o-(trifluoromethyl)phenyl]acetylene]

Masuda, Toshio; Hamano, Toshiyuki; Higashimura, Toshinobu; Ueda, Teruo; Muramatsu, Hiroshige

doi:10.1021/ma00180a001

Cited by 51 publications

(22 citation statements)

References 4 publications

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“…The results obtained on γ‐irradiation of alkynes 4–6 indicate that ortho ‐substitution favored polymerization with respect to the para ‐substituted PAs 1–3 . Nowadays, it is well recognized that ortho ‐substituted polyPAs obtained by transition metal catalyzed polymerization exhibit enhanced solubility, molecular weight, and filming properties than corresponding polyPAs derived from meta or para ‐substituted aryl alkynes 14,21–25. Therefore, the chemical yields and polymer properties of P4–P6 do not strictly derive from the activation source (irradiation vs. metal catalysis), but appear to be related to the nature of the growing carbon chain imposed by the ortho substituent in the course of the polymerization process.…”

Section: Resultsmentioning

confidence: 99%

“…The γ‐rays‐induced polymerization showed low reaction yields and molecular weights, except for 2,5‐disubstituted PAs in which yields and degrees of polymerization increased with ortho ‐substitution and with the number of the CF 3 groups in the phenyl ring 13. The interest in fluorine containing materials derived from the specific conductivity and nonlinear optical properties arising from the presence of both the conjugated double bonds and electron withdrawing groups, for example CF 3 , along the polymer backbone 14. In addition, fluorocarbon polymers are ideal candidates for the development of biomaterials due to their high thermal stability, inertness of the CF bond, and consequent biocompatibility 15…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of polyarylacetylenes by γ‐ray‐induced polymerization of terminal alkynes. Nanostructures of ortho‐substituted derivatives

Bassetti

Fratoddi

Lilla

et al. 2012

J. Polym. Sci. A Polym. Chem.

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Terminal aryl alkynes RC6H4CCH with substituents of different electronic properties and ring position (R = H, 4‐CF3, 4‐OMe, 2‐CF3, 2‐OMe, 2‐Me) were exposed to γ‐radiation (50–400 kGy) in organic solvents (hexane, 1,4‐dioxane, ethylacetate, methanol, tetrahydrofuran), at room temperature. The effects arising from substituent, solvent, dilution, and radiation dose allowed to define the conditions suitable for polymerization, which was favored in methanol at increasing dilution of the alkyne. Ortho‐substitution represented the key structural element in the substrate, and the derived polyarylacetylenes were characterized in detail, including gel permeation chromatography, thermal analysis, infrared, NMR, UV–vis, fluorescence, and scanning electron microscope spectroscopy. The results are consistent with the formation of irregular polymers mainly composed of trans‐transoid chains. Controlled aggregation of the polymers by means of an osmosis‐based procedure in solvent/non‐solvent mixtures allowed the formation of nanostructured materials, in particular of hollow nanospheres from THF/water. The methodology sets the basis for the development of γ‐rays‐induced polymerization of alkynes, in a transition metal catalyst‐free environment. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of polyarylacetylenes by γ‐ray‐induced polymerization of terminal alkynes. Nanostructures of ortho‐substituted derivatives

Bassetti

Fratoddi

Lilla

et al. 2012

J. Polym. Sci. A Polym. Chem.

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“…71 A mixture of WCl 6 with Ph 4 Sn was especially active as catalyst and achieved a high M w of 16 Â l0 5 . The product polymer was a dark brown solid, soluble in solvents such as toluene and CHCl 3 .…”

Section: Halogen-containing Polyacetylenesmentioning

confidence: 98%

Substituted polyacetylenes

Masuda

2006

J. Polym. Sci. A Polym. Chem.

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389

222

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This article reviews the chemistry of substituted polyacetylenes developed by our research group, more specifically, development of polymerization catalyst, synthesis of new polymers, elucidation of their structure, investigation of their properties, and development of their functions. The main features are as follows: a number of catalysts based on group 5, 6, and 9 transition metals (Nb, Ta, Mo, W, and Rh) have been developed, which include living polymerization catalysts. By using these catalysts, many new substituted polyacetylenes have been synthesized, whose molecular weights are very high (Mw = 104−106). Most of the polymers are soluble in many common solvents and stable enough in the air unlike polyacetylene. Some of these polymers exhibit interesting functions including high gas permeability and photoelectronic properties. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 165–180, 2007

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“…25, No. 6,1993 tion ratio YA/ Y 8 in the permeate divided by the concentration ratio XA/ X8 in the feed, where A and B indicate an organic liquid and water, respectively.…”

Section: Permeability Measurementmentioning

confidence: 99%

“…4 • 5 Thus phenylacetylene possessing a trifluoromethyl group at the ortho-position yields a high molecular weight polymer, leading to a good film forming ability of the polymer. 6 In the present study, poly[(2-trifluoromethy 1-5-perfl uoroalkylphenyl)acety lene] s were synthesized and their properties as separation membranes were evaluated.…”

mentioning

confidence: 99%