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Organotellurium-Mediated Radical Polymerization (TERP) Reagents

Organotellurium-mediated radical Ppolymerization (TERP), developed by Yamago et al., is a type of controlled radical polymerization (CRP) which is also known as reversible-deactivation radical polymerization (RDRP) or living radical polymerization (LRP). Controlled radical polymerization techniques allow easy control of molecular weights, provides polymers with narrow molecular weight distributions, and enables the synthesis of specialized structure polymers such as block copolymers, star shaped polymers, and hyperbranched polymers. Organotellurium compounds are employed as chain transfer agents (CTAs) for TERP.

TERP is advantageous for the development of functional polymers due to its wide monomer functional groups scope and the possibility of end group transformations. In addition, TERP offers a broader range of monomers that can be controlled with the same chain transfer agent compared to reversible addition-fragmentation chain transfer (RAFT) polymerization. This advantage contributes to an improved design flexibility in block copolymer synthesis.

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Reaction Examples of TERP

Polymerization by TERP can be carried out by thermal condition (Scheme 1), thermal condition with radical initiators (Scheme 2), or photoirradiation condition (Scheme 3). When applying the thermal condition with the addition of a radical initiator or the photoirradiation condition, polymerizations can proceed at lower temperatures compared to the thermal condition without radical initiators. In the case of methacrylate monomer polymerization, using only organotellurium chain transfer agents may lead to insufficient control of molecular weight distribution, so the addition of ditelluride compounds such as dimethyl ditelluride (Product No. D6090) or diphenyl ditelluride (Product No. D2718) is effective (Scheme 3). TERP is also effective for synthesizing block copolymers. For instance, the synthesis of diblock copolymers composed of N-isopropylacrylamide (NIPAAm), a more activated monomer (MAM), and N-vinylpyrrolidone (NVP), a less activated monomer (LAM), has been reported (Scheme 4). Additionally, synthesis of high molecular weight polystyrene via emulsion polymerization in an aqueous media using a chain transfer agent (Product No. M3728) having a carboxy group has also been reported (Scheme 5).6)

Scheme 1. Synthesis of polystyrene 3)

Scheme 1. Synthesis of polystyrene

Scheme 2. Synthesis of poly(N-isopropylacrylamide) 3)

Scheme 2. Synthesis of poly(N-isopropylacrylamide)

Scheme 3. Synthesis of poly(methyl methacrylate) 4)

Scheme 3. Synthesis of poly(methyl methacrylate)

Scheme 4. Synthesis of block copolymer 5)

Scheme 4. Synthesis of block copolymer

Scheme 5. Synthesis of high molecular weight polystyrene via emulsion polymerization 5)

Scheme 5. Synthesis of high molecular weight polystyrene via emulsion polymerization

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References

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