A New Class of Conjugated Ionic Polyacetylene. 2. Cyclopolymerization of Dihexyldipropargylammonium Salt by Metathesis Catalysts

Kim, Sung-Hyun; Choi, Sang-Jun; Park, Jong‐Wook; Cho, Hyun‐Nam; Choi, Sam‐Kwon

doi:10.1021/ma00086a059

Cited by 34 publications

(18 citation statements)

References 7 publications

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“…In the previous reports, we described the first synthesis of substituted ionic polyacetylenes by metathesis catalysts. , The monomers used were dihexyldipropargylammonium salts with bromide, tosylate, and tetraphenylborate counterions. These polymers are polyelectrolytes in which counterions are associated with the fixed ionic charges on the polymer backbone to maintain electroneutrality.…”

Section: Introductionmentioning

confidence: 99%

A New Class of Conjugated Ionic Polyacetylenes. 3. Cyclopolymerization of Alkyldipropargyl(4-sulfobutyl)ammonium Betaines by Transition Metal Catalysts

et al. 1997

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A new type of conjugated ionic polyacetylene was synthesized by metathesis polymerization of betaine monomers, alkyldipropargyl(4-sulfobutyl)ammonium betaines (ADPSAB). The alkyl groups used are ethyl, n-butyl, n-hexyl, and n-octyl. The polymerization of ADPSAB was carried out with various transition metal catalyst systems such as MoCl5-, WCl6-, and PdCl2-based catalyst systems. The MoCl5 and PdCl2 were found to be particularly effective catalysts for the cyclopolymerization of the betaine monomers. 1 H-NMR, 13 C-NMR, IR, and UV-visible spectroscopies showed that poly(ADPSAB) possess polyene structure having cyclic recurring units in the polymer backbone. Unlike polyelectrolyte, the resulting polymers were more soluble and showed higher viscosities in the salt solution than in salt-free solution (antipolyelectrolytes). When doped with an acceptor such as iodine, the polymers exhibited a substantial increase (∼10 -3 S/cm) in electrical conductivity compared to the undoped state (∼10 -10 S/cm).

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Section: Introductionmentioning

confidence: 99%

A New Class of Conjugated Ionic Polyacetylenes. 3. Cyclopolymerization of Alkyldipropargyl(4-sulfobutyl)ammonium Betaines by Transition Metal Catalysts

et al. 1997

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“…Et 3 SiH rather decreased the yield of polymer slightly. EtAlCl 2 , which had showed the high cocatalytic activity for some cyclopolymerization of dipropargyl monomers such as dipropargyl ether, 35 dihexyldipropargylammonium salts, 36 and dipropargylfluorene, 37 increased the yield of polymer slightly. The molecular weights (Mw) of resulting poly(DPSCH)s were relatively low in the range of 3,300-5,200 and the polydispersities were in the range of 1.48-1.92.…”

Section: Resultsmentioning

confidence: 99%

Cyclopolymerization of 1,1-Dipropargyl-1-silacyclohexane by Transition Metal Catalysts

2007

Bulletin of the Korean Chemical Society

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A conjugated spirocyclic polymer was synthesized via the cyclopolymerization of 1,1-dipropargyl-1-silacyclohexane with various transition metal catalysts. The monomer, 1,1-dipropargyl-1-silacyclohexane was synthesized by Grignard reaction of 1,1-dichloro-1-silacyclohexane with propargyl magnesium bromide. This polymerization proceeded well to give the corresponding poly(1,1-dipropargyl-1-silacyclohexane). The catalytic activity of WCl 6 was found to be similar with that of MoCl 5 . The structure of polymer having the conjugated backbone with silacyclohexane moieties was characterized by such instrumental methods as NMR ( 1 H-, 13 C-), IR, and UV-visible spectroscopies. The resulting polymers were mostly yellow or light-brown powders, depending on the catalyst systems used. This polymer was completely soluble in halogenated and aromatic hydrocarbons such as chloroform, 1,2-dichloromethane, benzene, toluene, and chlorobenzene, etc. The thermal and oxidative stabilities of polymer were also studied and discussed.

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“…[41 -43] The ionic polymers from dipropargylammonium derivatives having two n-hexyl substituents at N-atom were found to be completely soluble in polar solvents such as methanol, DMSO, DMF, THF, chloroform, etc. [44,45] This means that the solubility of polyacetylene derivatives depend on the substituents as well as the polymerization methods. The soluble ionic conjugated polymers will be very processible into thin homogeneous films, which may be an advantage for the applications as materials of organic semiconductors, chemical sensors, etc.…”

Section: Introductionmentioning

confidence: 99%

Polymerization of 4-Dimethylamino-N-propargylpyridinium Bromide by Transition Metal Catalysts

Gal

Jin

Gui

et al. 2003

Journal of Macromolecular Science, Part A

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The polymerization of an ionic propargyl derivative, 4-dimethylamino-N-propargylpyridinium bromide (DMAPPB), was carried out by palladium, platinum, and ruthenium chlorides. The polymerization of DMAPPB by these transition metal 401 catalysts proceeded well to give a relatively high polymer yield. The chemical structure of the resulting polymer was characterized by such instrumental methods as elemental analysis, infrared, NMR, UV -visible spectroscopies to have conjugated polymer backbone system bearing 4-dimethylamino-N-methylenepyridinium bromide. The polymer was soluble in DMF, DMSO, and formic acid, and found to be less hygroscopic than those of similar homologues having more smaller substituents. The resulting polymers were mostly black powders and showed the amorphous morphology.

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A New Class of Conjugated Ionic Polyacetylene. 2. Cyclopolymerization of Dihexyldipropargylammonium Salt by Metathesis Catalysts

Cited by 34 publications

References 7 publications

A New Class of Conjugated Ionic Polyacetylenes. 3. Cyclopolymerization of Alkyldipropargyl(4-sulfobutyl)ammonium Betaines by Transition Metal Catalysts

A New Class of Conjugated Ionic Polyacetylenes. 3. Cyclopolymerization of Alkyldipropargyl(4-sulfobutyl)ammonium Betaines by Transition Metal Catalysts

Cyclopolymerization of 1,1-Dipropargyl-1-silacyclohexane by Transition Metal Catalysts

Polymerization of 4-Dimethylamino-N-propargylpyridinium Bromide by Transition Metal Catalysts

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