Double Hydrophilic Poly(ethylene oxide)‐block‐Poly(dehydroalanine) Block Copolymers: Comparison of Two Different Synthetic Routes,Macromolecular Chemistry and Physics

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Double Hydrophilic Poly(ethylene oxide)‐block‐Poly(dehydroalanine) Block Copolymers: Comparison of Two Different Synthetic Routes
Macromolecular Chemistry and Physics ( IF 2.5 ) Pub Date : 2019-11-26 , DOI: 10.1002/macp.201900383
Johannes B. Max _{1,

2,

3} , Peter J. Mons _{1,

2,

3} , Jessica C. Tom _{1,

2,

3} , Felix H. Schacher _{1,

2,

3}

Affiliation

Two different synthetic pathways give access to the amphiphilic block copolymer poly(ethylene oxide)‐block‐poly(tert‐butoxycarbonylaminomethylacrylate). In the first approach, two end‐functionalized segments are linked via click chemistry; and in the second approach, a poly(ethylene oxide) (PEO) based macroinitiator is chain extended via atom transfer radical polymerization (ATRP). In both cases the linking unit consists of an amide group, which is necessary to effectively deprotect the corresponding polymer precursor without cleavage of both segments. For this, amide‐containing ATRP initiators are employed and successful synthesis by nuclear magnetic resonance (NMR) and size exclusion chromatography (SEC) analyses before comparing both pathways is demonstrated. After deprotection, a novel double hydrophilic block copolymer, poly(ethylene oxide)‐block‐poly(dehydroalanine), is obtained, which is investigated using SEC (aqueous and DMSO) and ¹H‐NMR spectroscopy. Containing a potentially zwitterionic PDha segment and a high density of both amino and carboxylic groups, pH‐dependent aggregation of the block copolymer is expected and is studied using dynamic light scattering, revealing interesting solution properties. The corresponding polymers are applied in various areas including drug delivery systems or in biomineralization.

中文翻译：

双重亲水性聚（环氧乙烷）-嵌段-聚（脱氢丙氨酸）嵌段共聚物：两种不同合成路线的比较

两种不同的合成途径给予访问两亲性嵌段共聚物的聚（环氧乙烷） -嵌段-聚（叔-丁氧基羰基氨基甲基丙烯酸酯）。第一种方法是通过点击化学将两个末端官能化的链段连接起来。在第二种方法中，通过原子转移自由基聚合（ATRP）使聚环氧乙烷（PEO）基大分子引发剂扩链。在两种情况下，连接单元均由酰胺基组成，该酰胺基对于有效脱保护相应的聚合物前体而不裂解两个链段是必需的。为此，使用了含酰胺的ATRP引发剂，并证明了在比较这两种途径之前，已通过核磁共振（NMR）和尺寸排阻色谱（SEC）分析成功进行了合成。脱保护后，一种新型的双亲水性嵌段共聚物，聚环氧乙烷嵌段获得了聚（脱氢丙氨酸），并使用SEC（水性和DMSO）和¹ H-NMR光谱进行了研究。包含潜在的两性离子PDha链段和高密度的氨基和羧基，嵌段共聚物的pH依赖性聚集是可预期的，并使用动态光散射进行了研究，揭示了有趣的溶液性质。相应的聚合物可应用于各种领域，包括药物输送系统或生物矿化。

更新日期：2019-11-26

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