Well-defined polymers with activated ester and protected aldehyde side chains for bio-functionalization

Hwang, Jenn Jiang; Li, Ronald C.; Maynard, Heather D.

doi:10.1016/j.jconrel.2007.04.010

Cited by 91 publications

(85 citation statements)

References 66 publications

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“…For an efficient RAFT polymerization (Scheme 1, Fig. 3 22* [86] S S MA [54] AAEMA [87] MAEP [87] MMA [88,89] AEMA [90] DMAEMA [91] (TPMMA) [92] TFPMA [93] St [48,94,95] 277 [96] 278 [96] 392 [97,98] 345 [99] 348 [100] 347 [101] St [51] 364 [102] 365 [102] NVP [103] 385 [104] 386 [98] 387 [104] 388 [104] 389 [104] 390 [104] BA/ 407 [105] St/MAH [53] AAEMA-b-AEP [87] AAEMA-b-MAEP [87] MAEP-b-AAEMA [87] BMA/TMSEMA [106] TFPMA-b-tBA [93] St-b-NIPAM [95] St-b-HEMA/DMAEMA [86] 364-b-384 [102] 365-b-384 [102] 386-b-392 [97] 23* [107] S CN S DEGMA [108] EGMA [108] MAA [108] MMA [109] PEGMA …”

Section: Choice Of Raft Agentsmentioning

confidence: 99%

“…Other monomers with reactive functionality that have been successfully (co)polymerized include 391 (with thiol reactive functionality) [161,162] and 392 (with protected aldehyde functionality) (Table 26). [97,98] Copolymers of monomers with reactive functionality, such as 371-392 (Tables 24-26), have potential application as scaffolds for bioconjugation. This and other applications are considered below in the section Polymer Brushes/Graft Copolymers/Comb Polymers/Surface Modification.…”

Section: Raft Polymer Synthesesmentioning

confidence: 99%

“…We found that with this method, while successful for removing the chain ends of polymers with a terminal MA unit, it was not possible to obtain complete removal of dithiobenzoate or butyl trithiocarbonate Table 26. Monomers with masked reactive functionality amenable to RAFT (co)polymerization 391 [161,162] O O S S N 392 [97,98] O O O O [94] BA C 12 H 25 S (159) EPHP [94] tBA C 12 H 25 S (135) EPHP [328] MMA C 12 H 25 S (121) EPHP [94] St Ph (22) EPHP [94] 358 Ph (22) B u 3 SnH [244] VAc C 2 H 5 O (227) B u 3 SnH [395] A Monomer unit adjacent to thiocarbonylthio group. B ((CH 3 ) 3 Si) 3 SiH -tris(trimethylsilyl)silane, EPHP -N-ethylpiperidine hypophosphite, Bu 3 SnH -tri-n-butylstannane.…”

Section: Radical-induced Reductionmentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

891

714

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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: Raft Polymer Synthesesmentioning

confidence: 99%

Section: Radical-induced Reductionmentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

891

714

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“…[92] Oximes and hydrazones are hydrolytically stable between pH 2-7 and 5-7, respectively, but they decompose rapidly above pH 9. [93,94] Aldehyde-functionalized polymers can be conveniently prepared from 3,3'-diethoxypropyl methacrylate, which can be polymerized using freeradical polymerization [95] as well as under ATRP [96] and RAFT [97] conditions. After polymerization, the acetal protecting group can be removed with trifluoroacetic acid.…”

Section: Modification Of Polymers Bearing Aldehydes and Ketonesmentioning

confidence: 99%

Synthesis of Functional Polymers by Post‐Polymerization Modification

2008

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Post-polymerization modification is based on the direct polymerization or copolymerization of monomers bearing chemoselective handles that are inert towards the polymerization conditions but can be quantitatively converted in a subsequent step into a broad range of other functional groups. The success of this method is based on the excellent conversions achievable under mild conditions, the excellent functional-group tolerance, and the orthogonality of the post-polymerization modification reactions. This Review surveys different classes of reactive polymer precursors bearing chemoselective handles and discusses issues related to the preparation of these reactive polymers by direct polymerization of appropriately functionalized monomers as well as the post-polymerization modification of these precursors into functional polymers.

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“…Further, the synthesis of diblock copolymers with styrene succeeded if the occurring homopolymers were removed. Maynard and coworkers 46,47 thus extended RAFT polymerization to p-nitrophenyl methacrylate and synthesized a diblock copolymer with diethoxypropyl methacrylate (DEPMA). The resulting diblock copolymer consisted of two reactive blocks featuring an orthogonal reactivity and the selective functionalization to yield a new diblock copolymer.…”

Section: Savariar and Thayumanavanmentioning

confidence: 99%

Synthesis of well‐defined polymeric activated esters

Théato

2008

J. Polym. Sci. A Polym. Chem.

271

258

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Monomers bearing an activated ester group can be polymerized under various controlled polymerization techniques, such as ATRP, NMP, RAFT polymerization, or ROMP. Combining the functionalization of polymers via polymeric activated esters with these controlled polymerization techniques generate possibilities to realize highly functionalized polymer architectures. Within this highlight two different research areas of activated esters in polymer science will be discussed: (i) the preparation of defined reactive polymer architectures by controlled polymerization techniques and (ii) the preparation of defined reactive thin films. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 6677–6687, 2008

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Well-defined polymers with activated ester and protected aldehyde side chains for bio-functionalization

Cited by 91 publications

References 66 publications

Living Radical Polymerization by the RAFT Process - A Second Update

Living Radical Polymerization by the RAFT Process - A Second Update

Synthesis of Functional Polymers by Post‐Polymerization Modification

Synthesis of well‐defined polymeric activated esters

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