First Aldehyde‐Functionalized Poly(2‐oxazoline)s for Chemoselective Ligation

Taubmann, Christian; Luxenhofer, Robert; Cesana, Sonia; Jordan, Rainer

doi:10.1002/mabi.200500059

Cited by 82 publications

(92 citation statements)

References 54 publications

(35 reference statements)

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“…The copolymers were found to be biocompatible materials suited for the immobilization of bioactive species. Jordan et al published a one-pot strategy for the synthesis of poly(2-oxazoline)s bearing a protected aldehyde functionalitiy in the side-chain [199]. The protected aldehyde group, a dioxalan, of the copolymer pMeOx-stat-p(DiOxal) n PrOx could be deprotected with trifluoroacetic acid; the aldehyde side-chains of the recovered copolymer pMeOx-stat-p(CHO) n PrOx reacted quantitatively with amino-oxy compounds such as O-benzylhydroxylamine hydrochloride.…”

Section: Click-reactions Involving Alkinesmentioning

confidence: 99%

Design Strategies for Functionalized Poly(2-oxazoline)s and Derived Materials

2013

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Abstract:The polymer class of poly(2-oxazoline)s currently is under intensive investigation due to the versatile properties that can be tailor-made by the variation and manipulation of the functional groups they bear. In particular their utilization in the biomedic(in)al field is the subject of numerous studies. Given the mechanism of the cationic ring-opening polymerization, a plethora of synthetic strategies exists for the preparation of poly(2-oxazoline)s with dedicated functionality patterns, comprising among others the functionalization by telechelic end-groups, the incorporation of substituted monomers into (co)poly(2-oxazoline)s, and polymeranalogous reactions. This review summarizes the current state-of-the-art of poly(2-oxazoline) preparation and showcases prominent examples of poly(2-oxazoline)-based materials, which are retraced to the desktop-planned synthetic strategy and the variability of their properties for dedicated applications.

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Section: Click-reactions Involving Alkinesmentioning

confidence: 99%

Design Strategies for Functionalized Poly(2-oxazoline)s and Derived Materials

2013

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“…Furthermore, numerous functional monomers allow the introduction of pendant functional side chains. Among others, carboxylic acid, [3,4] hydroxyl [3,5] and, more recently, amine, [6] thiol, [7] aldehyde [8] and alkyne [9] side chains are of particular interest for preparation of poly-and multifunctional polymer carriers for biomedical applications. Furthermore, the CROP of 2-oxazolines allows for the preparation of telechelics, [9,10] (multi)block-copolymers [11] or surface reactive lipopolymers.…”

Section: Introductionmentioning

confidence: 99%

Kinetic Investigations on the Polymerization of 2‐Oxazolines Using Pluritriflate Initators

Luxenhofer¹,

Bezen²,

Jordan³

2008

Macromol. Rapid Commun.

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In our ongoing efforts to develop poly(2‐oxazoline)s (POx) for biomedical applications, we report on the preparation of defined, star‐like hydrophilic POx. Using pluritriflate initiators, we show, through online kinetic measurements by gas chromatography, that multiple initiating groups are of equal reactivity for the initiation of the polymerization of 2‐oxazolines. The overall polymerization rate increases linearly with the number of initiator functions per molecule. Thus, all initiating moieties are of the same reactivity and all arms grow at the same rate. This is crucial for the establishment of a meaningful structure‐property relationship for polymers of star architectures.magnified image

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“…Functional groups, often protected, can be introduced into PAOx by making use of a functional monomer or initiator during the living cationic ring opening polymerisation (CROP, Scheme 1) of 2-oxazoline monomers or by using a functional terminating agent, yielding well-defined PAOx with control over number and type of functionalities [15,[29][30][31][32][33][34][35][36][37][38]. Methyl esters are especially interesting, because they can undergo a direct amidation with a variety of amines to easily introduce other functional groups such as alcohols, hydrazide and amines [39][40][41][42].…”

Section: Introductionmentioning

confidence: 99%

Thermal Properties of Methyl Ester-Containing Poly(2-oxazoline)s

et al. 2015

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This paper describes the synthesis and thermal properties in solution and bulk of poly(2-alkyl-oxazoline)s (PAOx) containing a methyl ester side chain.Homopolymers of 2-methoxycarbonylethyl-2-oxazoline (MestOx) and 2-methoxycarbonylpropyl-2-oxazoline (C3MestOx), as well as copolymers with 2-ethyl-2-oxazoline (EtOx) and 2-n-propyl-2-oxazoline (nPropOx), with systematic variations in composition were prepared. The investigation of the solution properties of these polymers revealed that the cloud point temperatures (T CP s) could be tuned in between 24˝C and 108˝C by variation of the PAOx composition. To the best of our knowledge, the T CP s of PMestOx and PC3MestOx are reported for the first time and they closely resemble the T CP s of PEtOx and PnPropOx, respectively, indicating similar hydrophilicity of the methyl ester and alkyl side chains. Furthermore, the thermal transitions and thermal stability of these polymers were investigated by DSC and TGA measurements, respectively, revealing amorphous polymers with glass transition temperatures between´1˝C and 54˝C that are thermally stable up to >300˝C.

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First Aldehyde‐Functionalized Poly(2‐oxazoline)s for Chemoselective Ligation

Cited by 82 publications

References 54 publications

Design Strategies for Functionalized Poly(2-oxazoline)s and Derived Materials

Design Strategies for Functionalized Poly(2-oxazoline)s and Derived Materials

Kinetic Investigations on the Polymerization of 2‐Oxazolines Using Pluritriflate Initators

Thermal Properties of Methyl Ester-Containing Poly(2-oxazoline)s

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