Crowned polyacetylene: 3. Synthesis and cation-binding property of polyphenylacetylene with azacrown cavity by cyclopolymerization of α,ω-bis(4′-ethynylphenoxy)oligooxyethylene containing a pyridyl unit

Kakuchi, Toyoji; Watanabe, Toshitaka; Matsunami, Shigeyuki; Kamimura, Hiroyuki; Haba, Osamu; Yokota, Kazuaki

doi:10.1016/s0032-3861(96)00624-6

Cited by 15 publications

(11 citation statements)

References 16 publications

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“…In a concentration range of 25-50 mol% of the catalyst, the yield of 5b raised insignificantly. Maximum yield of crown ether 5b was achieved by application of a strong solution of sodium hydroxide (entries 9-11) and of triethylene glycol tosylate as alkylating agent (entries [11][12][13][14].…”

Section: Methodsmentioning

confidence: 99%

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A Practical Synthesis of Benzocrown Ethers under Phase-Transfer Catalysis Conditions

Bogaschenko¹,

Basok²,

Kulygina³

et al. 2002

Synthesis

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Section: Methodsmentioning

confidence: 99%

“…It facilitates the preparation of new macrocyclic receptors (e. g. lariat crown ethers 10 ) and polymers with unusual properties. 11,12 In this respect benzocrown ethers have advantages over their aliphatic analogs because of the possibility of easy introduction of the substituents in the benzene ring.…”

mentioning

confidence: 99%

A Practical Synthesis of Benzocrown Ethers under Phase-Transfer Catalysis Conditions

Bogaschenko¹,

Basok²,

Kulygina³

et al. 2002

Synthesis

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“…Kakuchi reported the Rh-catalyzed cyclopolymerization of bis(ethynylbenzene) tethered by ethylene glycol spacers with or without pyridine unit ( 168 ; Figure ). − [Rh(nbd)Cl] 2 /amine and Rh(nbd)BPh 4 were utilized as the catalyst. The cyclopolymerization was conducted in highly dilute condition ([monomer] = 0.01–0.05 mol L –1 ), in order to avoid gel formation.…”

Section: Cyclopolymerization Of Diynes Eneynes and Bis(cycloolefin)smentioning

confidence: 99%

Cyclopolymerizations: Synthetic Tools for the Precision Synthesis of Macromolecular Architectures

2018

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Monomers possessing two functionalities suitable for polymerization are often designed and utilized in syntheses directed to the formation of cross-linked macromolecules. In this review, we give an account of recent developments related to the use of such monomers in cyclopolymerization processes, in order to form linear, soluble macromolecules. These processes can be activated by means of radical, ionic, or transition-metal mediated chain-growth polymerization mechanisms, to achieve cyclic moieties of variable ring size which are embedded within the polymer backbone, driving and tuning peculiar physical properties of the resulting macromolecules. The two functionalities are covalently linked by a "tether", which can be appropriately designed in order to "imprint" elements of chemical information into the polymer backbone during the synthesis and, in some cases, be removed by postpolymerization reactions. The two functionalities can possess identical or even very different reactivities toward the polymerization mechanism involved; in the latter case, consequences and outcomes related to the sequence-controlled, precision synthesis of macromolecules have been demonstrated. Recent advances in new initiating systems and polymerization catalysts enabled the precision syntheses of polymers with regulated cyclic structures by highly regio- and/or stereoselective cyclopolymerization. Cyclopolymerizations involving double cyclization, ring-opening, or isomerization have been also developed, generating unique repeating structures, which can hardly be obtained by conventional polymerization methods.

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“…Nickel salts are well-known to cyclotrimerize, cyclotetramerize, and to polymerize acetylene, producing benzene, cyclooctatetraene, and amorphous presumably low molecular weight poly(acetylene). − Recently, there have been several reports of the polymerization of acetylene derivatives using late-transition-metal catalysts based on rhodium, − palladium, and nickel. − Late-transition-metal catalysts are particularly attractive as they tend to exhibit greater functional group tolerance than the more electron-deficient early-transition-metal catalysts. To our knowledge, these catalysts have not been applied to the synthesis of poly(cyanoacetylene).…”

Section: Introductionmentioning

confidence: 99%

Preparation of Poly(cyanoacetylene) Using Late-Transition-Metal Catalysts

et al. 1999

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Poly(cyanoacetylene) has been prepared by polymerization of cyanoacetylene using a variety of late-transition-metal (Pd- and Ni-based) catalysts. The effect of reaction conditions on molecular weight and polymer yield was explored. Significant catalyst residues remain in the polymer samples. However, spectra are consistent with the proposed poly(cyanoacetylene) structure. Notable differences in molecular weight, effective conjugation length, and ability to undergo thermal cyclization to a supposed aromatic ladder polymer were observed between these polymers and those prepared using conventional anionic or radical initiators.

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Crowned polyacetylene: 3. Synthesis and cation-binding property of polyphenylacetylene with azacrown cavity by cyclopolymerization of α,ω-bis(4′-ethynylphenoxy)oligooxyethylene containing a pyridyl unit

Cited by 15 publications

References 16 publications

A Practical Synthesis of Benzocrown Ethers under Phase-Transfer Catalysis Conditions

A Practical Synthesis of Benzocrown Ethers under Phase-Transfer Catalysis Conditions

Cyclopolymerizations: Synthetic Tools for the Precision Synthesis of Macromolecular Architectures

Preparation of Poly(cyanoacetylene) Using Late-Transition-Metal Catalysts

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