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Squaramide-Based Self-Associating Amphiphiles for Anion Recognition
ChemPlusChem ( IF 3.4 ) Pub Date : 2021-07-12 , DOI: 10.1002/cplu.202100275
Lokesh K Kumawat 1 , Conor Wynne 1, 2 , Emanuele Cappello 3 , Peter Fisher 1 , Luke E Brennan 1 , Alessandro Strofaldi 1 , Jennifer J McManus 1, 2, 4 , Chris S Hawes 5 , Katrina A Jolliffe 6 , Thorfinnur Gunnlaugsson 2, 3 , Robert B P Elmes 1, 2, 7
Affiliation  

The synthesis and characterisation of two novel self-assembled amphiphiles (SSAs) SQS-1 and SQS-2 are reported. Both compounds, based on the squaramide motif, were fully soluble in a range of solvents and were shown to undergo self-assembly through a range of physical techniques. Self-assembly was shown to favour the formation of crystalline domains on the nanoscale but also fibrillar film formation, as suggested by SEM analysis. Moreover, both SQS-1 and SQS-2 were capable of anion recognition in DMSO solution as demonstrated using 1H NMR and UV/Vis absorption spectroscopy, but displayed lower binding affinities for various anions when compared against other squaramide based receptors. In more competitive solvent mixtures SQS-1 gave rise to a colourimetric response in the presence of HPO42− that was clearly visible to the naked eye. We anticipate that the observed response is due to the basic nature of the HPO42− anion when compared against other biologically relevant anions.

中文翻译:

用于阴离子识别的基于方酰胺的自缔合两亲物

报告了两种新型自组装两亲物 (SSA) SQS-1SQS-2的合成和表征。这两种基于方酰胺基序的化合物完全可溶于多种溶剂,并通过一系列物理技术进行自组装。SEM 分析表明,自组装有利于纳米级晶域的形成,也有利于纤维状薄膜的形成。此外,使用1 H NMR 和 UV/Vis 吸收光谱证明, SQS-1SQS-2都能够识别 DMSO 溶液中的阴离子,但与其他基于方酰胺的受体相比,对各种阴离子的结合亲和力较低。在更具竞争力的溶剂混合物中,SQS-1在 HPO 4 2−存在下产生肉眼清晰可见的比色响应。我们预计,与其他生物学相关阴离子相比,观察到的反应是由于 HPO 4 2−阴离子的基本性质所致。
更新日期:2021-08-05
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