Polymerization of 1‐aryl‐2‐trimethylsilylacetylenes by transition metal catalysts(II)

Gal, Yeong‐Soon; Choi, Sung‐Yool; Kim, Chung-Yup

doi:10.1002/pola.1989.080270103

Cited by 17 publications

(11 citation statements)

References 10 publications

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“…It had been also found the similar reaction of the disubstituted polyacetylenes having aromatic substituents (phenyl, 2-thienyl, and 2-furyl) instead 140 GAL AND LEE of n-butyl substituent proceeded completely [47]. The complete desilylation may be due to the excellent solubility of the resulting monosubstituted polyacetylene.…”

Section: Resultsmentioning

confidence: 87%

“…We reported the polymerization of silicon-containing disubstituted acetylenes, 1-aryl-2-trimethylsilylacetylenes (aryl: phenyl, 2-thienyl, 2-furyl, 2-pyridyl) using various transition metal catalysts [46,47]. This paper deals with the synthesis of silicon-containing disubstituted polyacetylene having n-butyl and trimethylsilyl groups as substituents and the characterization of the resulting polymer.…”

Section: Introductionmentioning

confidence: 98%

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Polymerization of 1-Butyl-2-Trimethylsilylacetylene by Transition Metal Catalysts

Gal

Lee

2000

Journal of Macromolecular Science, Part A

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New silicon-containing disubstituted polyacetylene was prepared by the polymerization of BTMSA having two bulky substituents (n-butyl and trimethylsilyl) using transition metal catalysts. The polymerization proceeded in a mild manner and the final polymer yield was generally lower than those of silicon-containing monosubstituted acetylenes by the similar catalyst system. The characterization on the polymer structure revealed that the resulting poly(BTMSA) have a conjugated backbone system, but the polymers have peculiar copolymer composition of poly-(BTMSA) and poly(1-hexyne) due to the spontaneous desilylation during the polymerization. The fluoride-ion induced desilylation of poly(BTMSA) using n-Bu 4 N + F -in THF yielded a completely desilylated product, pure poly(1-hexyne).

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Section: Resultsmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 98%

Polymerization of 1-Butyl-2-Trimethylsilylacetylene by Transition Metal Catalysts

Gal

Lee

2000

Journal of Macromolecular Science, Part A

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“…We have prepared various polyacetylenes with different functionalities, which retain extensive conjugation [1,15,[18][19][20]. A new family of conjugated polymers was prepared through the activated polymerization of ethynylpyridines by using functional alkyl halides [17,[21][22][23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a Polyacetylene Derivative Containing Amine Functional Groups

Gal

Jin

2012

Molecular Crystals and Liquid Crystals

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A monosubstituted polyacetylene having amine functional groups was prepared via the polymerization of 3-ethynylaniline by using transition metal catalysts. The polymerization proceeded well in homogeneous manner to give a relatively high yield of polymer. The polymer structure was characterized by such instrumental methods as IR, NMR, and UV-visible spectroscopies to have the conjugated backbone system with the designed functional groups. The absorption spectrum starts around 700 nm, which is due to the π → π * interband transition of conjugated polymer system. This polymer exhibited the irreversible electrochemical behaviors between the doping and undoping peaks.

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“…Though poly(pyrrol)s are the most frequently used conducting polymers, poly(ene)s are still among the most investigated conjugated polymers. They are accessible via ADMET (acyclic diene metathesis) polymerization starting from ®;!-dienes [7 -12], via ROMP (ring-opening metathesis polymerization) of poly(ene) precursors [13][14][15][16][17][18][19][20][21][22][23] or, preferably, via alkyne polymerization techniques (Scheme 1) [13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Regio- and stereospecific cyclopolymerization of 1,6-heptadiynes and 1,5-hexadiynes

Anders¹,

Krause²,

Wang³

et al. 2004

Designed Monomers and Polymers

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The synthesis of poly(ene)s exclusively based on one single repetitive unit, i.e., 1,2cyclopent-2-enylenvinylenes,is described. Polymers containing >96% 1,2-cyclopent-2-enylenvi nylene units were obtained by low-temperature-initiated cyclopolymerization of diethyl dipropargylmalonate (DEDPM) by Mo(N-2,6-i-Pr 2-C 6 H 3)(CHCMe 2 Ph)(OCH(CH 3 / 2 / 2. In the presence of quinuclidine, >96% 5-membered ring structures were realized at room temperature, e.g., using Mo(N-2,6-Me 2-C 6 H 3)(CHCMe 2 Ph)(OC(CH 3 / 3 / 2. 4-(Ethoxycarbonyl)-4-(1S, 2R,5S)-(C)-menthyl-1,6-heptadiyne was cyclopolymerized to determine the con guration of the double bond (i.e., the cis/ trans ratio) and the tacticity of the poly(ene) backbone. Poly(4-(ethoxycarbonyl)-4-(1S,2R,5S)-(C)-menthyl-1,6heptadiyne) again consisted of >96% 5-membered rings and possessed an all-trans tactic, presumably isotactic structure. A linear plot of number of monomers added (N) vs. molecular weight suggested that cyclopolymerization of DEDPM proceeded in a living manner. At least a class-V living system was con rmed by the stepwise synthesis of poly(DEDPM). Molecular weight distributions (PDIs) of 1.16-1.37 resulted from ratios of the rate constants for polymerization (k p) to initiation (k i), k p =k i À 1. In uences of temperature, the base and steric and electronic effects of the arylimido and alkoxy ligand are presented. Complementary to the use of well-de ned Schrock initiators, poly(DEDPM) containing exclusively 5-membered rings was accessible by the use of the quaternary systems MoCl 5-n-Bu 4 Sn-EtOH-quinuclidineand MoOCl 4-n-Bu 4 Sn-EtOH-quinuclidine. Though virtually identical polymers were obtained, the polymerization systems themselves were controlled, yet not living, as is the case with Schrock initiators. Selected polymer properties such as stability, degradation behavior, conductivity, and thermoresponsive behavior will be discussed. Finally, the polymerization behavior of other monomers such as N,N-dipropargylaniline (1), dipropargyl sul de (2), 1,8-diethynylnaphthalene (3) and 1,2-diethynyltetramethyldisilane (4) is presented.

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Polymerization of 1‐aryl‐2‐trimethylsilylacetylenes by transition metal catalysts(II)

Cited by 17 publications

References 10 publications

Polymerization of 1-Butyl-2-Trimethylsilylacetylene by Transition Metal Catalysts

Polymerization of 1-Butyl-2-Trimethylsilylacetylene by Transition Metal Catalysts

Synthesis and Characterization of a Polyacetylene Derivative Containing Amine Functional Groups

Regio- and stereospecific cyclopolymerization of 1,6-heptadiynes and 1,5-hexadiynes

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