Functional RAFT agents for radical‐controlled polymerization: Quantitative synthesis of trithiocarbonates containing functional groups as RAFT agents using equivalent amount of CS<sub>2</sub>

Aoyagi, Naoto; Endō, Takeshi

doi:10.1002/pola.23410

Cited by 48 publications

(45 citation statements)

References 41 publications

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“…108 [275] St [71,275] (St-b-BA) [275] S S S 109 [284] S S S 110* [283] BA [70] tBA [283] AM [285] St [70,286] St-b-NIPAM [286] tBA [284] St [284] tBA-b-St [284] St-b-BA [284] St/AA [287] St/AA-b-St [287] St/MAH/NVP [288,289] (Continued) [290] 111b RЈ ϭ C 2 H 5 [290] 111c RЈ ϭ i C 3 H 7 [290] 111d RЈ ϭ t C 4 H 9 [290] 111e RЈ ϭ CH 2 Ph [290] 112 [290] S…”

Section: *unclassified

“…Symmetrical trithiocarbonates are frequently synthesized from the corresponding halide, and carbon disulfide in the presence of a base. Aoyagi and Endo [290] have shown that this process can be performed on benzyl halides, and stoichiometric carbon disulfide at low temperature (40 • C) in air with potassium bicarbonate as base to provide near quantitative yields of the corresponding dibenzyl trithiocarbonates (111)(112)(113)(114).…”

Section: Synthesis Of Raft Agentsmentioning

confidence: 99%

“…114 [290] S S S 115 [291,292] S S S 116 [292] St [291,292] St-b-NIPAM [291] St [292] 117 S S S HO 2 C C O 2 H (St) [71] A See footnote A of Table 3. B See footnote B of Table 3.…”

Section: *mentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

906

720

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This paper provides a second update to the review of reversible deactivation radical polymerization achieved with thiocarbonylthio compounds (ZC(=S)SR) by a mechanism of reversible addition-fragmentation chain transfer (RAFT) that was published in June 2005 (Aust. J. Chem. 2005, 58, 379-410). The first update was published in November 2006 (Aust. J. Chem. 2006, 59, 669-692). This review cites over 500 papers that appeared during the period mid-2006 to mid-2009 covering various aspects of RAFT polymerization ranging from reagent synthesis and properties, kinetics and mechanism of polymerization, novel polymer syntheses and a diverse range of applications. Significant developments have occurred, particularly in the areas of novel RAFT agents, techniques for end-group removal and transformation, the production of micro/nanoparticles and modified surfaces, and biopolymer conjugates both for therapeutic and diagnostic applications.

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Section: *unclassified

Section: Synthesis Of Raft Agentsmentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

906

720

View full text Add to dashboard Cite

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“…However, it could only be successfully employed to prepare polyfunctional RAFT agents of very low degree of polymerization at room temperature. At elevated temperatures or longer reaction times, a side-product was formed, presumably because of the reaction of the dibromide's ester groups [43]. The second strategy (procedure 2) was based on the formation of the trithiocarbonate anions on the surface of an anion exchange resin.…”

Section: Preparation Of the Polyfunctional Raft Agentsmentioning

confidence: 99%

Multiblock Copolymers of Styrene and Butyl Acrylate via Polytrithiocarbonate-Mediated RAFT Polymerization

Ebeling

Vana

2011

Polymers

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Abstract:When linear polytrithiocarbonates as Reversible Addition-Fragmentation chain Transfer (RAFT) agents are employed in a radical polymerization, the resulting macromolecules consist of several homogeneous polymer blocks, interconnected by the functional groups of the respective RAFT agent. Via a second polymerization with another monomer, multiblock copolymers-polymers with alternating segments of both monomers-can be prepared. This strategy was examined mechanistically in detail based on subsequent RAFT polymerizations of styrene and butyl acrylate. Size-exclusion chromatography (SEC) of these polymers showed that the examined method yields low-disperse products. In some cases, resolved peaks for molecules with different numbers of blocks (polymer chains separated by the trithiocarbonate groups) could be observed. Cleavage of the polymers at the trithiocarbonate groups and SEC analysis of the products showed that the blocks in the middle of the polymers are longer than those at the ends and that the number of blocks corresponds to the number of functional groups in the initial RAFT agent. Furthermore, the produced multiblock copolymers were analyzed via differential scanning calorimetry (DSC). This work underlines that the examined methodology is very well suited for the synthesis of well-defined multiblock copolymers.

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“…38 Furthermore, symmetrical trithiocarbonates were readily prepared by use of potassium carbonate in acetonitrile under mild conditions (Scheme 15). 39 Significant advantages, such as the use of available reagents, high reactivity, and excellent yields of products demonstrated the excellent efficiency of this methodology to synthesize symmetrical trithiocarbonates. In other reports, the synthesis of trithiocarbonates was carried out under similar conditions by use of relatively strong bases.…”

Section: The Synthesis Of Trithiocarbonatesmentioning

confidence: 98%