Synthesis of Reactive Telechelic Polymers Based on Pentafluorophenyl Esters

Roth, Peter J.; Wiss, Kerstin T.; Zentel, Rudolf; Théato, Patrick

doi:10.1021/ma801681b

Cited by 102 publications

(122 citation statements)

References 50 publications

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“…St [169] 287 [170] S O N 3 O S CN 27 [171] St [169,171,172] DMAM [171] St-b-DMAM [171] DMAM-b-St [171] [173] DEGMA [173] LMA [89,173] MMA [173] PEGMA [89,173] NIPMAM [173] 29 [174] O N 3 O S S CN St [174] (Continued) [176] 33* [180] PEO macro-RAFT agent [180] 34 [181] PEO macro-RAFT agent [182] G1 dendron RAFT agent D (ar-3,5-substitution)…”

Section: Choice Of Raft Agentsmentioning

confidence: 99%

“…It was reported that aminolysis of PNIPAM trithiocarbonate proceeds quantitatively to the thiol when conducted in the presence of a [370] MMA Ph (28) AIBN [173] MMA Ph (28) 393 [173] MMA C 10 H 7 (42) AIBN B [194] 416 Ph (25) ACVA C [164,474] DMAPMAM Ph (25) AIBN [168] NIPAM C 2 H 5 S (185) 394 [368] NIPAM C 2 H 5 S (189) 394 [374] NIPAM C 12 H 25 S (139) AIBN [324] NIPAM S(PDMAM-b-PNIPAM) (398) AIBN [475] DMAM S(PDMAM) (398) AIBN [475] NAM/NAS C 12 H 25 S (115) AIBN [299] St Ph (24) AIBN [133] St C 4 H 9 S (160) AIBN D [473] St Ph (50) 395 [476] St S(PSt) (398) AIBN [475] VAc small amount of a phosphine reducing agent (TCEP). [371,372] Two groups have compared aminolysis with borohydride reduction for PSt dithiobenzoate.…”

Section: Aminolysis/hydrolysis/ionic Reductionmentioning

confidence: 99%

“…RAFT agents with active ester functionality on 'R' include: 28, 31, 133. [173] • The pyridyl disulfide-thiol reaction. RAFT agents with pyridyl disulfide functionality on 'Z' include: 181-184.…”

Section: Click Reactionsmentioning

confidence: 99%

See 2 more Smart Citations

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: Choice Of Raft Agentsmentioning

confidence: 99%

Section: Aminolysis/hydrolysis/ionic Reductionmentioning

confidence: 99%

See 1 more Smart Citation

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

show abstract

“…Lowe and coworkers, 84 and Summerlin and coworkers 52 have used the thiol-ene addition reaction 8,52,80,83,84,86,87 and RAFT polymerization to build macromonomers and more complex architectures such as star polymers. In what follows we describe our approach to macromonomer syntheses using simultaneous aminolysis and thiolene reaction to diacrylates.…”

Section: Mannose-methacrylate Conjugationmentioning

confidence: 99%

Modification of RAFT‐polymers via thiol‐ene reactions: A general route to functional polymers and new architectures

Boyer

Granville

Davis

et al. 2009

J. Polym. Sci. A Polym. Chem.

239

240

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An investigation into the aminolysis of x-end groups of RAFT-polymers and simultaneous thiol-ene reactions with ene-bearing compounds is described. Three different polymers, P(MMA), P(HPMA), and P(NIPAAm), with low PDIs were synthesized using dithiobenzoate and trithiocarbonate RAFT agents. P(NIPAAm) synthesized with trithiocarbonate RAFT agent and P(HPMA) synthesized with dithiobenzoate RAFT agent were both functionalized with a methacrylate-modified mannose and a maleimide-modified biotin via one-pot simultaneous aminolysis and thiol-ene reactions with product yields above 85%. The presence of ene-compounds during aminolysis was shown to prevent the formation of disulfide interchain crosslinking. Using the same approach, P(MMA), P(HPMA), and P(NIPAAm) were converted to (meth)acrylate macromonomers with high yields ([80%). In the case of P(MMA), the simultaneous aminolysis and thiol-ene addition prevented any intrachain side reactions, i.e., thiolactone formation. New architectures such as graft and block copolymers were successfully generated from the macromonomers.

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“…[15][16][17] Fortunately, progress in conjugation chemistry has resulted in a variety of efficient reactions that are particularly useful for the functionalization of polymers, 18,19 including the well-established copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC), [20][21][22] or more traditional activated ester-mediated ligations. [23][24][25] However, despite the use of these highly efficient reactions, the grafting-to approach often requires an excess of polymer and subsequent purification of the conjugate to remove unreacted polymers. 26,27 The grafting-from synthetic strategy enables the use of a wider range of monomers, as it is not limited by monomer side chain functionalities that are orthogonal with the chain end group used for the conjugation, as in the grafting-to route.…”

Section: Introductionmentioning

confidence: 99%

Cyclic peptide–polymer conjugates: Grafting‐to vs grafting‐from

Larnaudie

Brendel

Jolliffe

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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A systematic comparison between the grafting-to (convergent) and grafting-from (divergent) synthetic routes leading to cyclic peptide-polymer conjugates is described. The reversible addition-fragmentation chain transfer (RAFT) process was used to control the polymerizations and the couplings between cyclic peptide and polymer or RAFT agent were performed using N-hydroxysuccinimide (NHS) active ester ligation. The kinetics of polymerization and polymer conjugation to cyclic peptides were studied for both grafting-to and grafting-from synthetic routes, using N-acryloyl morpholine as a model monomer. The cyclic peptide chain transfer agent was able to mediate polymerization as efficiently as a traditional RAFT agent, reaching high conversion in the same time scale while maintaining excellent control over the molecular weight distribution. The conjugation of polymers to cyclic peptides proceeded to high conversion, and the nature of the carbon at the a-position to the NHS group was found to play a crucial role in the reaction kinetics. The study was extended to a wider range of monomers, including hydrophilic and temperature responsive acrylamides, hydrophilic and hydrophobic acrylates, and hydrophobic and pH responsive methacrylates. Both approaches lead to similar peptide-polymer conjugates in most cases, while some exceptions highlight the advantages of one or the other method, thereby demonstrating their complementarity.

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Synthesis of Reactive Telechelic Polymers Based on Pentafluorophenyl Esters

Cited by 102 publications

References 50 publications

Living Radical Polymerization by the RAFT Process - A Second Update

Living Radical Polymerization by the RAFT Process - A Second Update

Modification of RAFT‐polymers via thiol‐ene reactions: A general route to functional polymers and new architectures

Cyclic peptide–polymer conjugates: Grafting‐to vs grafting‐from

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