“Clickable” polymers via a combination of RAFT polymerization and isocyanate chemistry

Moraes, John; Maschmeyer, Thomas; Perrier, Sébastien

doi:10.1002/pola.24710

Cited by 27 publications

(19 citation statements)

References 77 publications

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“…14). [192,243,288] RAFT polymerization and the thiocarbonylthio group is compatible with isocyanate functionality. However, some care must be taken in selection of the RAFT agent and other components of the polymerization medium such that they do not also contain other functionality that is inherently reactive (such as carboxy).…”

Section: Monomers With Reactive Functionalitymentioning

confidence: 99%

“…The method has also been used as a degrafting process in silicasupported polymer synthesis. [594] 412 [243] 413 [192] 414 [288] 415 [192] 416 [587] 417 [203] O 407 [235,254] 408 [586] 409 [356] 410 [250] 411 [445] 418 [322] 419 [322] 420 [588] 421 [256,377,588] 422 [427] 423 [461,463] HDDA 424 [461,463] 425 [461] …”

Section: Radical-induced Reductionmentioning

confidence: 99%

“…St [192] AA [207] AA/BA [325] AA/PEGA [207] St-bSt/413 [192] AA-b-PEGA [207] DMAm [442] DMAm-b-St [442] 157 S S S CO 2 H HO 2 C A* St [107] 158…”

mentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process – A Third Update

2012

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This paper provides a third update to the review of reversible deactivation radical polymerization (RDRP) achieved with thiocarbonylthio compounds (ZC(¼S)SR) by a mechanism of reversible addition-fragmentation chain transfer ( Chem. 2009Chem. , 62, 1402. This review cites over 700 publications that appeared during the period mid 2009 to early 2012 covering various aspects of RAFT polymerization which include reagent synthesis and properties, kinetics and mechanism of polymerization, novel polymer syntheses, and a diverse range of applications. This period has witnessed further significant developments, particularly in the areas of novel RAFT agents, techniques for end-group transformation, the production of micro/nanoparticles and modified surfaces, and biopolymer conjugates both for therapeutic and diagnostic applications.

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Section: Monomers With Reactive Functionalitymentioning

confidence: 99%

Section: Radical-induced Reductionmentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process – A Third Update

2012

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“…13 Another possible method of reducing S mis-insertions is to utilize α-methyl styrene (AMS) as the comonomer in place of S. AMS has a very low ceiling temperature (61°C), therefore polymerization at or above this temperature results in a rate of depolymerization that is greater than the rate of homopolymerization. [17][18][19][20][21][22][23] TMI has also been shown to be capable of being homopolymerized and copolymerized cationically. 8 Although AMS-MalA copolymerization will provide control over the final copolymer substructure, well defined polymer molecular weight and polymer dispersity at present are not possible to obtain as controlled radical polymerization techniques, such as ATRP and RAFT, are ineffective for these monomers.…”

Section: Introductionmentioning

confidence: 99%

Alternating copolymers of functionalized α-methyl styrene monomers and maleic anhydride

2015

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Alkyl and tertiary amine functionalized α-methyl styrene (AMS) monomers have been synthesized via reactive coupling of 3-isopropenyl-α,α-dimethylbenzyl isocyanate (TMI) with primary amines. Primary amines utilized include hexylamine, octadecylamine and N,N-dimethylethylenediamine to synthesize monomers,urea (AMSDMA), respectively. The structures of these functionalized AMS monomers have been confirmed by 1 H-NMR, 13 C-NMR and FT-IR. AMS, AMSC 6 or AMSC 18 was then successfully copolymerized with maleic anhydride (MalA) via free radical polymerization initiated by azobisisobutyronitrile to synthesize alternating copolymers. Free radical homopolymerizations of AMS, AMSC 6 , AMSC 18 and MalA were performed to reveal no monomer conversion by gas chromatography and no formation of polymer chains by gel permeation chromatography (GPC). Alternating copolymers were characterized by GPC, 1 H-NMR, FT-IR and MALDI-TOF MS. Finally, post-polymerization modification of P[(AMSC 18 )-a-(MalA)] by imidization of the MalA repeat unit with a primary amine was performed. This leads to the synthesis of alternating dual functionalized copolymers in an efficient and simple way. † Electronic supplementary information (ESI) available. See

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“…C). PABTC is a class of trithiocarbonate RAFT agents that have been shown to be applicable for controlling polymerization of N,N ‐dimethylacrylamide (DMA) , acrylic acid , methyl methacrylate , and styrene monomers. This amphipathic RAFT agent is soluble in water and produces a radical similar to that of the propagating species upon fragmentation.…”

Section: Introductionmentioning

confidence: 99%

Sieving polymer synthesis by reversible addition fragmentation chain transfer polymerization

2013

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Replaceable sieving polymers are the fundamental component for high resolution nucleic acids separation in CE. The choice of polymer and its physical properties play significant roles in influencing separation performance. Recently, reversible addition fragmentation chain transfer (RAFT) polymerization has been shown to be a versatile polymerization technique capable of yielding well defined polymers previously unattainable by conventional free radical polymerization. In this study, a high molecular weight PDMA at 765 000 gmol-1 with a PDI of 1.55 was successfully synthesized with the use of chain transfer agent - 2-propionic acidyl butyl trithiocarbonate (PABTC) in a multi-step sequential RAFT polymerization approach. This study represents the first demonstration of RAFT polymerization for synthesizing polymers with the molecular weight range suitable for high resolution DNA separation in sieving electrophoresis. Adjustment of pH in the reaction was found to be crucial for the successful RAFT polymerization of high molecular weight polymer as the buffered condition minimizes the effect of hydrolysis and aminolysis commonly associated with trithiocarbonate chain transfer agents. The separation efficiency of PABTC-PDMA was found to have marginally superior separation performance compared to a commercial PDMA formulation, POP™-CAP, of similar molecular weight range.

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“Clickable” polymers via a combination of RAFT polymerization and isocyanate chemistry

Cited by 27 publications

References 77 publications

Living Radical Polymerization by the RAFT Process – A Third Update

Living Radical Polymerization by the RAFT Process – A Third Update

Alternating copolymers of functionalized α-methyl styrene monomers and maleic anhydride

Sieving polymer synthesis by reversible addition fragmentation chain transfer polymerization

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