Sequence control in one-step condensation polymerization

Ueda, Mitsuru

doi:10.1016/s0079-6700(99)00014-3

Cited by 56 publications

(48 citation statements)

References 39 publications

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“…For example, in stepgrowth polymerizations, precise periodic primary structures can be synthesized if appropriate monomers and linking chemistries are used. [5,16,17] In chain-growth polymerizations, fascinating regular microstructures such as alternating AB, [18,19] AAB, [18,20] or ABC [21] can be also obtained. Still, these interesting examples remain exceptions rather than the norm.…”

Section: Introductionmentioning

confidence: 99%

Tailored Polymer Microstructures Prepared by Atom Transfer Radical Copolymerization of Styrene and N‐substituted Maleimides

Lutz¹,

Schmidt²,

Pfeifer³

2011

Macromol. Rapid Commun.

132

124

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In the present Feature Article, a kinetic strategy for controlling the microstructure of synthetic polymer chains prepared via a radical chain‐growth polymerization process is presented. This approach was recently developed in our laboratory and relies on the controlled kinetic addition of ultrareactive N‐substituted maleimides during the atom transfer radical polymerization of styrene. This method is experimentally straightforward and can be applied to a broad library of functional N‐substituted maleimides. Thus, this platform allows synthesis of unprecedented polymer materials such as 1D macromolecular arrays. The basic kinetic requirements, the experimental conditions, and the synthetic scope of this approach are discussed in details herein. magnified image

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Section: Introductionmentioning

confidence: 99%

Tailored Polymer Microstructures Prepared by Atom Transfer Radical Copolymerization of Styrene and N‐substituted Maleimides

Lutz¹,

Schmidt²,

Pfeifer³

2011

Macromol. Rapid Commun.

132

124

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“…Sequence specificity is achieved through either copolymerization of XaX and YbY type monomers (alternatdoi: 10.1007/s11426-015- ing copolymer) or homopolymerization of XabY type sequence built-in monomers. An extensive review on sequence control in traditional condensation polymerization was published by Ueda [23]. In the following section, we will focus on systems involving effective coupling reactions between sequence built-in monomers.…”

Section: Step Growth Polymerizationmentioning

confidence: 99%

Recent developments in the synthesis of sequence controlled polymers

2015

Sci. China Chem.

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“…On the other hand, in step-growth polymerization system, Ueda developed successful sequence control in the one-step condensation polymerization. 60 In a series of studies on the reactions of thiiranes or oxiranes with carboxylic acid derivatives, we examined the addition reactions of oxiranes or thiiranes with cyclic S-thioesters in the presence of quaternary onium salts or crown ether complexes. The reaction of PGE with -thiobutyrolactone (TBL) using …”

Section: Ring-opening Alternating Copolymerization Of Oxiranes With Cmentioning

confidence: 99%

Novel Synthesis of Polymers with Well-Defined Structures Based on Selective Reaction of Cyclic Sulfides and Cyclic Ethers Catalyzed by Quaternary Onium Salts

Kameyama

Nishikubo

2009

Polym. J.

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Novel syntheses of polymers with well-defined structures were developed on the basis of the selective reactions of thiiranes and oxiranes with carboxylic esters or active chlorides using quaternary onium salts. (1) A new type of reactive polymers with pendant chloromethyl groups was synthesized by polyaddition of difunctional thiiranes or oxiranes with various organic dichlorides. (2) Polysulfides with controlled molecular weight and narrow molecular weight distribution were synthesized by ring-opening polymerization of thiiranes with carboxylic acid derivatives as initiators and quaternary onium salts as catalysts, in which acyl-groups transfer to the propagating center in each propagation step. The ring-opening polymerization of thiiranes has an advantage in the synthesis of specific shaped polymers such as star polymers and cyclic polymers. (3) Novel A-B type sequence-ordered copolymers were synthesized by alternating ring-opening polymerization of oxiranes withthiobutyrolactone, or of oxetane with cyclic carboxylic anhydrides. (4) Sequence-ordered polymers were successfully synthesized on the basis of a new concept-''transformation of polymer backbones'' using insertion of thiiranes and oxiranes into poly(S-thioester)s in the aforementioned reaction systems. The reaction mechanism and advantages of the reaction systems are also discussed.KEY WORDS: Ring-opening Reaction / Thiirane / Oxirane / Quaternary Onium Salts / Acyl Transfer / Sequence-ordered Polymers / Addition reactions of cyclic compounds such as cyclic ethers with certain reagents are useful synthetic methods for preparing polymeric materials. The addition reactions of oxiranes (epoxy) compounds have been used for syntheses of functional polymers from reactive polymers containing pendant oxirane groups.1 Epoxy resins with multiple oxirane groups are widely utilized with certain curing reagents to obtain thermal cured materials.2 These polymer syntheses are based on the addition reaction of oxiranes with such reagents as amines, carboxylic acids, etc. In general, the reactions provide mixtures of -addition and -addition products (mixtures of regio-isomers).3 Regioselective ring-opening reactions of oxiranes are important research subjects in synthetic organic chemistry, 4 but it has been thought that the reactions of oxiranes with the reagents mentioned are not suitable for precise syntheses of polymers with well-defined structures.Recently, we have developed synthetic methods for functional polymers and chemical modification of polymers based on the regioselective ring-opening reactions of oxiranes with carboxylic esters catalyzed by quaternary onium salts. 5 In a series of studies on ring-opening reaction of cyclic compounds with several reagents; we found novel regioselective reactions of thiiranes or oxiranes to be useful for syntheses of polymers with well-defined structures.A significant advantage of the addition reactions of thiiranes or oxiranes with the reagents is the selective formation ofaddition products without ring-opening polymeriza...

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Sequence control in one-step condensation polymerization

Cited by 56 publications

References 39 publications

Tailored Polymer Microstructures Prepared by Atom Transfer Radical Copolymerization of Styrene and N‐substituted Maleimides

Tailored Polymer Microstructures Prepared by Atom Transfer Radical Copolymerization of Styrene and N‐substituted Maleimides

Recent developments in the synthesis of sequence controlled polymers

Novel Synthesis of Polymers with Well-Defined Structures Based on Selective Reaction of Cyclic Sulfides and Cyclic Ethers Catalyzed by Quaternary Onium Salts

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