Synthesis and polymerization of 4-vinylquinoline and 4-vinylpyridine with AlEt3-VCl3: Influence of pyridine as donor ligand

Benito, Y.; Rodriguez, Jorge H.

doi:10.1016/0014-3057(94)90112-0

Cited by 4 publications

(2 citation statements)

References 11 publications

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“…A linear correlation between the reaction time and molecular weight was observed, indicating the living polymerization behavior in this system . The controlled coordination polymerization of VP has rarely been explored, except in the case of the AlEt 3 –VCl 3 catalyst …”

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confidence: 99%

End-Functionalized Polymerization of 2-Vinylpyridine through Initial C–H Bond Activation of N-Heteroaromatics and Internal Alkynes by Yttrium Ene–Diamido Complexes

et al. 2011

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confidence: 99%

End-Functionalized Polymerization of 2-Vinylpyridine through Initial C–H Bond Activation of N-Heteroaromatics and Internal Alkynes by Yttrium Ene–Diamido Complexes

et al. 2011

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“…Although poly(vinylpyridines) have received considerable attention, substituted pyridine monomers are scarcely used in the polymerization, presumably due to severe steric hindrances. , On the other hand, polymers obtained from these monomers have shown potential, for example, as chromatographic materials for the selective separation of actinides and lanthanides. − Encouraged by the successful polymerization of 4VP by RE/YPhos Lewis pairs, a series of 4VP derivatives were also tested in the presence of this catalytic system ( 1 / P2 ), and the results are summarized in Table . Substitution of the 4VP ortho -position with an electron-donating methoxy group resulted in rapid polymerization with a 1 mol % catalyst loading and quantitatively yielded the corresponding PMVP polymer with M n = 44.0 kg/mol and Đ = 1.23 (Table , entry 1).…”

Section: Resultsmentioning

confidence: 99%

Rare-Earth Aryloxide/Ylide-Functionalized Phosphine Frustrated Lewis Pairs for the Polymerization of 4-Vinylpyridine and Its Derivatives

Zhao

Zhang

et al. 2021

Macromolecules

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This work reports the efficient polymerization of 4-vinylpyridine (4VP) using Lewis pairs composed of homoleptic rare-earth (RE) aryloxides and ylide-functionalized phosphines (YPhos). The resultant P4VP was readily quaternized by the addition of 1-bromododecane. Polymerization of 4VP derivatives (2-methoxy-4-vinylpyridine, 4-vinylquinoline, and 2,6dimethyl-4-vinylpyridine) also occurred under identical reaction conditions. The RE/YPhos Lewis pair polymerization system effectively copolymerized 4VP with methyl methacrylate, which resulted in copolymers with gradient architectures and narrow molecular weight distributions. A combined experimental and computational study provided critical insights into the polymerization mechanism. Density functional theory calculations also revealed that the use of YPhos as a Lewis base greatly facilitated both the initiation and subsequent monomer insertion in comparison with PEt 3 .

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Thermal analysis of 1,4‐di[n′‐(quinolyl)]buta‐1,3‐diynes, structure, and topo‐oligomerization: Polymerization of 3‐ethynylquinoline with the triethyl aluminum/vanadium 2,4‐pentanedionate catalyst system

Rodriguez¹,

Lafuente²,

Rı́os³

2004

J. Polym. Sci. A Polym. Chem.

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Conjugated 1,4-bis(nЈ-quinolyl)-1,3-butadiynes were obtained through the oxidative dimerization of the corresponding nЈ-ethynylquinolines catalyzed by cuprous chloride. Differential scanning calorimetry analysis of the 1,4-bis[nЈ-(quinolyl)]buta-1,3-diyne molecules produced evidence of a syn-anti rotational equilibrium around the 1,3-diyne axis and an irreversible transformation into a thermopolymer. The topooligomerization of 1,4-bis[3Ј-(quinolyl)]buta-1,3-diyne, which took place by irradiation with sunlight, was investigated with matrix-assisted laser desorption/ionization timeof-flight mass spectrometry. Accurate X-ray molecular structure and refinement analysis of 1,4-bis[3Ј-(quinolyl)]buta-1,3-diyne was conducted. The molecular crystalline packing consisted of parallel arrays of two groups of centrosymmetric molecules (antirotamer) in a herringbone assemblage in the solid state. The polymerization of 3-ethynylquinoline was carried out with the AlEt 3 /V(acac) 3 system to produce a mixture of 1,2,4-and 1,3,5-tris(3Ј-quinolyl)benzene cyclotrimers and a trans-cisoid polyene structure. RESULTS AND DISCUSSION Synthesis of n-Ethynylquinolines [2-Ethynylquinoline (1), 3-Ethynylquinoline (2), and 4-Ethynylquinoline (3)]1-3 were satisfactory obtained through the Sonogashira cross-coupling of an n-haloquinoline and 2-methyl-3-butyn-2-ol catalyzed by palladium. 11,12

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Synthesis and polymerization of 4-vinylquinoline and 4-vinylpyridine with AlEt3-VCl3: Influence of pyridine as donor ligand

Cited by 4 publications

References 11 publications

End-Functionalized Polymerization of 2-Vinylpyridine through Initial C–H Bond Activation of N-Heteroaromatics and Internal Alkynes by Yttrium Ene–Diamido Complexes

End-Functionalized Polymerization of 2-Vinylpyridine through Initial C–H Bond Activation of N-Heteroaromatics and Internal Alkynes by Yttrium Ene–Diamido Complexes

Rare-Earth Aryloxide/Ylide-Functionalized Phosphine Frustrated Lewis Pairs for the Polymerization of 4-Vinylpyridine and Its Derivatives

Thermal analysis of 1,4‐di[n′‐(quinolyl)]buta‐1,3‐diynes, structure, and topo‐oligomerization: Polymerization of 3‐ethynylquinoline with the triethyl aluminum/vanadium 2,4‐pentanedionate catalyst system

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