Complex radical polymerization of methyl methacrylate in the presence of heterocyclic ferrocene derivatives

Monakov, Yu. B.; Islamova, Regina M.; Golovochesova, O. I.; Utepova, Irina A.; Musikhina, Alexandra A.; Чупахин, О. Н.

doi:10.1134/s001250081005006x

Dokl Chem

2010

DOI: 10.1134/s001250081005006x

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Complex radical polymerization of methyl methacrylate in the presence of heterocyclic ferrocene derivatives

Yu. B. Monakov

Regina M. Islamova

O. I. Golovochesova

et al.

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Cited by 4 publications

(3 citation statements)

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“…The synergetic effect of the metal-and nitrogencontaining groups has been the most striking in the cases of azinyl ferrocenes 8-12 [62][63][64]. Combining the studied hetarylferrocenes with peroxides has afforded the highly efficient catalytic/initiating systems, more active in comparison with the ferrocene 1-benzoyl peroxide system, other conditions being the same.…”

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Iron compounds in controlled radical polymerization: Ferrocenes, (clathro)chelates, and porphyrins

Islamova

2016

Russ J Gen Chem

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Abstract-Experimental data on the application of metal complexes in radical polymerization of vinyl monomers collected over the recent 15 years have been analyzed and generalized. Special attention has been given to (un)substituted ferrocenes, macrocyclic (clathro)chelates, and iron porphyrinates as well as to the approaches to enhance their catalytic activity in controlled synthesis of macromolecules. The mentioned systems have been compared with each other as well as with selected complexes of other transition metals. It has been shown that the electronic and spatial structures of the metal complexes are related to their efficiency in the radical polymerization reactions. Keywords: controlled radical polymerization, metallocene, (clathro)chelate, metal porphyrinate, catalytic/ initiating system Application of metal complexes opens broad prospects to control the polymerization processe and to prepare polymer materials with improved physicochemical properties. The metal complex catalysis has become of special importance in the field of controlled radical polymerization over the recent 15 years.The term "controlled radical polymerization" is generally referred to "living" or "pseudo-living" radical polymerization; its mechanism, irrespectively of the type of the catalysts/mediators applied (metal complexes [1-11], nitroxyl compounds [12-14], thioesters [15,16], etc.) is based on minimization of the probability of the interaction between the propagating radicals, resulting in the irreversible chain termination. This allows for control of molecular parameters of the prepared polymers, in particular, reduction of the polydispersity coefficient down to M w /M n = 1.1, achieving the linear behavior of the number-average molecular mass (M n ) as function of the conversion, elimination of the undesirable gel effect, and preparation of block copolymers.Atom Transfer Radical Polymerization (ATRP) [1], Transition Metal-Catalyzed Living Radical Polymerization [7], and Organometallic Mediated Radical Polymerization (OMRP) [11] are among the types of controlled radical polymerization. The first approach is based on the use of halides of organic complexes of transition metals, leading to the formation of labile terminal carbon-halogen bond (P n -Hlg). Under certain conditions, this bond is capable of dissociation to regenerate the initial or new active radical further propagating the polymer chain (Scheme 1).Here P n · stands for the propagating macroradical, М is the vinyl monomer, HlgMt x+1 /L is the metal complex halide (with L as the organic ligand), Mt is the transition metal, and k p is the rate constant of the chain propagation.The second of the listed methods uses stable radical organometallic species or diamagnetic transition metal complexes forming the carbon-metal bond P n -Mt as the regulators of the polymer chain growth [11] (Scheme 2).Due to the similarity of these two approaches their simultaneous operation is often assumed [11].Besides "living" radical polymerization, complexand/or coordination-radical polymeri...

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“…N,N-Dimethyl-N-(methylferrocenyl)amine 7 [22,61] and azinyl derivatives of ferrocene 8-12 (Scheme 4) [62][63][64] have been chosen.…”

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Iron compounds in controlled radical polymerization: Ferrocenes, (clathro)chelates, and porphyrins

Islamova

2016

Russ J Gen Chem

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“…The polydispersity index M w /M n was of 1.3-3.0 depending on the monomer conversion, being in general lower than in the case when the radiacl initiator was used alone (M w /M n = 2.0-4.0). Molecular mass parameters confirmed the influence of the additive on the chain growth and chain termination steps [1,2].…”

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Azinyl derivatives of ferrocene for preparation of poly(methyl methacrylate) with enhanced properties

Islamova

Yarmukhamedova

2014

Russ J Gen Chem

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Abstract-Influence of 1-[pyridyl-2]-, 1-[quinolin-2-yl]-, 1-[acridin-9-yl]-, 1-[pyrazin-2-yl]-, and 1-[pyrimid-4-yl]-ferrocenes on heat and thermomechanical properties of the produced poly(methyl methacrylate) has been studied.Keywords: azinyl ferrocene, poly(methyl methacrylate), radical polymerization, initiator, thermal properties, thermomechanical properties ISSN 1070-3632, Russian Journal of General Chemistry, 2014, Vol. 84, No. 12, pp. 2472-2474. © Pleiades Publishing, Ltd., 2014. Original Russian Text © R.M. Islamova, E.I. Yarmukhamedova, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 12, pp. 2056-2058 Metal complexes are highly promising for application in controlled polymerization processes and for preparation of polymeric materials with enhanced physico-chemical properties. It was demonstrated that the metal complexes I-V combined with diacyl peroxides (benzoyl peroxide or lauryl peroxide) form highly efficient initiating systems, more active than the systems based on unsubstituted ferrocene [3][4][5], allowing for fast polymerization with high yield at lower temperatures (30-60)°С. The spectral studies confirmed that both ferrocenyl and heterocyclic fragments of compounds I-V affected the coordination with peroxide initiator [2]. LETTERS TO THE EDITORThe mentioned ferrocenes did not interact with azobisisobutyronitrile AIBN but the overall polymerization rate of methyl methacrylate polymerization was somewhat increased, pointing at the influence of the azinyl ferrocenes on the chain growth processes in addition to that on the initiation step [2].

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Regioselective synthesis of 1-azinyl-1′-isopropenylferrocenes

Musikhina

Utepova

Чупахин

et al. 2020

Mendeleev Communications

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Complex radical polymerization of methyl methacrylate in the presence of heterocyclic ferrocene derivatives

Cited by 4 publications

References 3 publications

Iron compounds in controlled radical polymerization: Ferrocenes, (clathro)chelates, and porphyrins

Iron compounds in controlled radical polymerization: Ferrocenes, (clathro)chelates, and porphyrins

Azinyl derivatives of ferrocene for preparation of poly(methyl methacrylate) with enhanced properties

Regioselective synthesis of 1-azinyl-1′-isopropenylferrocenes

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