Dithiocarbamates as universal reversible addition-fragmentation chain transfer agents

Destarac, Mathias; Charmot, Dominique; Franck, X.; Zard, Samir Z.

doi:10.1002/1521-3927(20001001)21:15<1035::aid-marc1035>3.0.co;2-5

Cited by 352 publications

(355 citation statements)

References 2 publications

(5 reference statements)

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“…Systems studied by mass spectrometry include (polymer/ RAFT agents): PNIPAM/20,22, [78] PNIPAM/39,40, [93] PVAc/49, [48] PS/21, [126] PS/69, [106] PMMA/8,11, [100] PBA/ 57,63, [127] PMA/21,22,24, [81,83] PEA/79, [49] and poly-(acenaphthalene)/81. [128] ESI is a softer ionization technique than MALDI-TOF and is more likely to leave the end groups intact to be observed in the mass spectrum.…”

Section: Evidence In Support Of the Raft Mechanismmentioning

confidence: 99%

“…Electron-withdrawing substituents on Z can enhance the activity of RAFT agents to modify the above order. [38,[46][47][48][49] Thus, xanthate and dithiocarbamate RAFT agents where the oxygen or nitrogen lone pair is less available for delocalization with the C S by virtue of being part of an aromatic ring or by possessing an adjacent electron-withdrawing substituent are substantially more effective. For examples see Table 6 (xanthates) or Table 4 (dithiocarbamates).…”

mentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process

Moad¹,

Rizzardo²,

Thang³

2005

Aust. J. Chem.

2,133

1,894

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This paper presents a review of living radical polymerization achieved with thiocarbonylthio compounds [ZC( S)SR] by a mechanism of reversible addition-fragmentation chain transfer (RAFT). Since we first introduced the technique in 1998, the number of papers and patents on the RAFT process has increased exponentially as the technique has proved to be one of the most versatile for the provision of polymers of well defined architecture. The factors influencing the effectiveness of RAFT agents and outcome of RAFT polymerization are detailed. With this insight, guidelines are presented on how to conduct RAFT and choose RAFT agents to achieve particular structures. A survey is provided of the current scope and applications of the RAFT process in the synthesis of well defined homo-, gradient, diblock, triblock, and star polymers, as well as more complex architectures including microgels and polymer brushes.

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Section: Evidence In Support Of the Raft Mechanismmentioning

confidence: 99%

mentioning

confidence: 99%

Living Radical Polymerization by the RAFT Process

Moad¹,

Rizzardo²,

Thang³

2005

Aust. J. Chem.

2,133

1,894

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“…The organostibines are also compatible with a variety of polar functional groups. Consequently, the polymerization of NIPAM, AN, and VP proceeded in a highly controlled manner and gave the desired polymers in excellent yields (entries [9][10][11][12][13][14].…”

Section: Sbrpmentioning

confidence: 99%

“…Significant advances have been reported during the past decade, and a variety of highly controlled and practical methods have been introduced. 4,5 Three representative methods, which are known as nitroxide-mediated radical polymerization, 6 atom transfer radical polymerization, 7,8 and reversible addition-fragmentation chain transfer (RAFT) radical polymerization, 9,10 are now widely used in the synthesis of a variety of advanced materials. However, the development of a more versatile process is still needed to further enhance the ability of macromolecular engineering for the tailored synthesis of, for example, random, block, and graft copolymers and comb, hyperbranched, and network polymers.…”

Section: Introductionmentioning

confidence: 99%

Development of organotellurium‐mediated and organostibine‐mediated living radical polymerization reactions

Yamago

2005

J. Polym. Sci. A Polym. Chem.

174

103

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Organotelluriummediated living radical polymerizations (TERPs) and organostibinemediated living radical polymerizations (SBRPs) provide well-defined polymers with a variety of polar functional groups via degenerative chain-transfer polymerization. The high controllability of these polymerizations can be attributed to the rapid degenerative-transfer process between the polymer-end radicals and corresponding dormant species. The versatility of the methods allows the synthesis of AB diblock, ABA triblock, and ABC triblock copolymers by the successive addition of different monomers. This review summarizes the current status of TERP and SBRP.

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“…As a consequence, the initiatorderived chains were not always readily discernable [12][13][14][15]. Several groups tried to use the matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) [16][17][18][19] and electrospray-ionization-quadrupole time-of-flight mass spectrometry (ESI-TOF-MS) [11] to identify the chain end structures of the RAFT polymers. The results did show signals corresponding to polymers with initiatorderived end groups.…”

Section: Introductionmentioning

confidence: 99%

Reversible Addition-Fragmentation Chain Transfer (RAFT) Polymerization of Vinyl Monomers Initiated by Poly(methyl methacrylate) Peroxide

Zhang

Zhu

et al. 2007

E-Polymers

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Poly(methyl methacrylate) peroxide (PMMAP) was synthesized and used as the initiator in the reversible addition-fragmentation chain transfer (RAFT) polymerization. Methyl methacrylate (MMA) as the monomer and 2-cyanoprop-2-yl 1-dithionaphthalate (CPDN) as the chain transfer agent was used in the polymerization system. The polymerization was successfully initiated by PMMAP while maintaining features of "living"/controlled radical polymerization such as the number-average molecular weights (M n ) increasing linearly with the monomer conversions and low polydispersity index (PDI) values. The results of 1 H NMR and IR spectra confirmed that a small quantity of polymer chains were derived from the PMMAP moieties. The PMMAP can also initiate the RAFT polymerization of styrene (St) and methyl acrylate (MA), and the polymerization proceeded in a "living"/controlled fashion.

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Dithiocarbamates as universal reversible addition-fragmentation chain transfer agents

Cited by 352 publications

References 2 publications

Living Radical Polymerization by the RAFT Process

Living Radical Polymerization by the RAFT Process

Development of organotellurium‐mediated and organostibine‐mediated living radical polymerization reactions

Reversible Addition-Fragmentation Chain Transfer (RAFT) Polymerization of Vinyl Monomers Initiated by Poly(methyl methacrylate) Peroxide

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