For the first time amphiphilic receptors based on the 1,3-alternate stereoisomeric form of thiacalix[4]arene, bearing carboxyl/sulphonate polar headgroups on one side and 10,12-pentacosadiynoic acid (PCDA) residues on another side of the macrocyclic plane, were synthesized. It was shown that embedding of synthesized macrocycles in PCDA vesicles results in stable colloids with a size around 300 nm. The temperature of ultrasonication before UV irradiation has a critical impact on the packing of vesicles for better polymerization. The increase of calixarene content in PCDA vesicles causes a decrease in the degree of PCDA polymerization. Nevertheless, calixarene additives dramatically change the colorimetric response of photopolymerized PCDA vesicles toward metal ions. Vesicles with 10 mol% content of calixarene have significant colorimetric response toward lanthanide ions with a detection limit up to 8 μM. The colorimetric response in the series of lanthanide ions depends on the ionic radius, and the greatest response was found for the largest La(III) ion. It was found that binding of calixarene–PCDA vesicles with lanthanide ions results in the formation of large 1 μm aggregates followed by sedimentation. Thus, the mechanism of colorimetric response of calixarene-decorated polydiacetylene vesicles toward lanthanide ions includes the distortion of the calixarene cavity provoking perturbation of the PDA backbone accompanied by metal-induced aggregation of functionalized vesicles with sedimentation of particles. Therefore, calixarene–PCDA vesicles have great potential for the future design of bifunctional colloids with sensor and separation applications.

中文翻译：

---

对-叔丁基硫杂杯[4]芳烃与10,12-戊二十二碳二烯酸的1，3-交替立体异构形式的 新型两亲性共轭物。存在金属离子时的合成和色性质†

首次基于1,3-交替的两亲性受体合成了在大环平面的一侧带有羧基/磺酸根极性头基并在另一侧带有10,12-戊二碳二烯酸（PCDA）残基的噻唑杯[4]芳烃的立体异构体形式。结果表明，将合成的大环化合物嵌入PCDA囊泡可产生大小约为300 nm的稳定胶体。UV照射之前的超声处理温度对囊泡的包装具有至关重要的影响，以实现更好的聚合。PCDA囊泡中杯芳烃含量的增加导致PCDA聚合度降低。然而，杯芳烃添加剂极大地改变了光聚合的PCDA囊泡对金属离子的比色响应。杯芳烃含量为10 mol％的囊泡对镧系元素离子具有显着的比色响应，检测限高达8μM。III）离子。发现杯芳烃-PCDA囊泡与镧系离子的结合导致形成大的1μm聚集体，然后沉淀。因此，杯状芳烃修饰的聚二乙炔囊泡对镧系元素离子的比色响应机制包括杯状芳烃腔的变形，引起PDA主链的扰动，伴随着金属诱导的功能化囊泡的聚集以及颗粒的沉淀。因此，杯芳烃-PCDA囊泡在未来设计具有传感器和分离应用的双功能胶体方面具有巨大潜力。