Highly stable polysulfone anion exchange membranes incorporated with bulky alkyl substituted guanidinium cations†,Molecular Systems Design & Engineering

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Highly stable polysulfone anion exchange membranes incorporated with bulky alkyl substituted guanidinium cations†
Molecular Systems Design & Engineering ( IF 3.2 ) Pub Date : 2019-07-12 , DOI: 10.1039/c9me00064j
Boxin Xue _{1,

2,

3,

4,

5} , Fen Wang _{1,

2,

3,

4,

5} , Jifu Zheng _{1,

2,

3,

4,

5} , Shenghai Li _{1,

2,

3,

4,

5} , Suobo Zhang _{1,

2,

3,

4,

5}

Affiliation

A series of guanidinium-based cations with various N-substituted groups (methyl, ethyl, isopropyl, cyclobutyl, benzyl and phenyl) were synthesized and their alkaline stabilities were evaluated by ¹H NMR analysis. The results indicated that the contribution of the substituent group toward the stability followed the sequences: isopropyl > ethyl > benzyl > phenyl and ethyl > methyl > cyclobutyl. The relative stability sequences suggested that free and bulky alkyl substituent groups with large steric hindrance can dramatically improve the alkaline stability. Tetraethyl-benzyl-isopropyl guanidinium showed the highest alkaline stability which remained unchanged after treatment with 1 mol L⁻¹ KOH/CD₃OD at 60 °C for 312 h. Novel polysulfone anion exchange membranes (AEMs) with such stable guanidinium cations were prepared via iridium-catalyzed C–H activation and the Suzuki–Miyaura reaction. The obtained guanidinium functionalized AEM exhibited excellent resistance to alkaline solutions (after immersing in 1 mol L⁻¹ NaOH at 60 °C for 30 days, no degradation was observed), indicating that AEMs functionalized by guanidiniums with large steric hindrance are very promising materials for AEM applications.

中文翻译：

高度稳定的聚砜阴离子交换膜，结合了庞大的烷基取代的胍盐阳离子†

合成了一系列具有各种N-取代基（甲基，乙基，异丙基，环丁基，苄基和苯基）的胍基阳离子，并通过¹ H NMR分析评估了其碱性稳定性。结果表明，取代基对稳定性的贡献遵循以下顺序：异丙基>乙基>苄基>苯基和乙基>甲基>环丁基。相对稳定性序列表明具有大空间位阻的游离的和庞大的烷基取代基可以显着提高碱稳定性。四乙基-苄基-异丙基胍鎓盐显示出最高的碱稳定性，在用1 mol L ^-1 KOH / CD ₃处理后，碱稳定性保持不变在60℃下OD 312小时。通过铱催化的C–H活化和Suzuki–Miyaura反应制备了具有这种稳定胍盐阳离子的新型聚砜阴离子交换膜（AEM）。所获得的胍基官能化的AEM对碱溶液表现出优异的耐受性（在60°C的1 mol L ^-1 NaOH中浸泡30天后，未观察到降解），表明通过具有大空间位阻的胍鎓官能化的AEM是非常有前途的材料AEM应用程序。

更新日期：2019-10-07

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