Selenium-containing polymers: synthesis and applications

Elzbieta Wojaczynska,Andrzej Trochimczuk,Girolamo Cirrincione

doi:10.24820/ark.5550190.p011.077

Elzbieta Wojaczynska, Andrzej Trochimczuk + Show 1 more

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https://doi.org/10.24820/ark.5550190.p011.077

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Abstract

Selenium-containing polymers: synthesis and applications

Highlights

Reagent was used to obtain polydiselenide with R = biphenyl.[10]
In two subsequent publications the authors studied the kinetics of the addition reaction and the effect of substituents in ethynylbenzene as a model for addition polymerization in order to clarify the details of addition polymerization of 1,4-benzenediselenol and 1,4diethynylbenzene.[13,14]
Organoselenium reagents and catalysts are widely used in organic synthesis, mainly due to relative ease of carbon-selenium bond cleavage.[45,46,47,48]

Summary

Selenium Compounds as RAFT Agents

Another field of polymer chemistry where selenium-containing compounds and selenium-containing polymers were investigated is controlled radical polymerization (CRP). A RAFT mechanism was suggested in the polymerization of styrene in the presence of phosphinodiselenoic esters[35] and in the presence of P,P-diphenyl phosphinodiselenoic acid benzyl ester.[36] Earlier photopolymerization of styrene with diphenyldiselenide afforded polystyrene with phenylseleno groups at both end of chains.[37] A cyclic compound, 5,5-dimethyl-3-phenyl-2-selenoxo-1,3selenazolidin-4-one (Figure 5), was used in the RAFT polymerization of vinyl acetate.[38] The authors reported a slightly lower polydispersity index of poly(vinyl acetate) in the case of a selenium-containing chain transfer agent than in the case of sulfur-containing analog Another RAFT agent, 4-cyanopentanoic acid diselenobenzoate was used in the controlled polymerization of 4-vinylpyridine.[39] The agent was immobilized on the surface of silicon and the poly(vinyl pyridine) chains were growing from the surface. An interesting approach to the synthesis of topological selenium-containing polymers, involving the use of borohydride ion-exchange resin to react with Se and serve as a source of this element, has been reported (Scheme 8).[41] By methods such as those described above, both the topology and the MW of the product can be controlled by the proper choice of the polymeric precursor.

Application of Selenium-containing Polymers in Chemical Synthesis

CH3Se2

Findings

Conclusions