The article presents the synthesis of novel 13- and 16-membered azobenzocrown derivatives with peripheral thiol moieties and preliminary studies assessing their possible application in plasmonic sensors based on gold nanoparticles. The effect of the length of the chain connecting the macrocycle with the thiol group and the effect of the presence of the additional functional compound, i.e. lipoic acid, on the sensor response was analyzed. Colloidal gold nanoparticles modified with a 16-membered crown with a thiol group on oxyethylene (compound 12) or oxybutylene (compound 13) linker was found to have good properties, allowing for detection of potassium ions in aqueous solutions at concentrations 8-20 mM for bifunctionalized nanogold and 4-26 mM for less stable, colloidal gold modified only with thiol derivatives of azobenzocrowns. The response towards potassium cations of bifunctionalized nanogold modified with compound 13 was more stable in time than for the system incorporating compound 12. Compound 13, obtained with the highest yield among all presented thiol derivatives of azobenzocrowns, was selected for further, more detailed, studies.

中文翻译：

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偶氮苯冠醚硫醇衍生物的合成。偶氮基和硫辛酸功能化金纳米粒子识别碱金属离子的初步研究

本文介绍了具有外围硫醇部分的新型 13 和 16 元偶氮苯冠衍生物的合成，以及评估它们在基于金纳米粒子的等离子体传感器中可能应用的初步研究。分析了连接大环与硫醇基团的链长度的影响以及附加功能性化合物（即硫辛酸）的存在对传感器响应的影响。发现用 16 元冠修饰的胶体金纳米粒子在氧乙烯（化合物 12）或氧丁烯（化合物 13）接头上具有硫醇基团具有良好的特性，允许检测浓度为 8-20 mM 的水溶液中的钾离子双功能化纳米金和 4-26 mM 用于稳定性较差的胶体金，仅用偶氮苯并冠的硫醇衍生物修饰。