Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water
作者:Rocco Bussolati、Pasquale Carrieri、Andrea Secchi、Arturo Arduini、Alberto Credi、Monica Semeraro、Margherita Venturi、Serena Silvi、Diana Velluto、Romina Zappacosta、Antonella Fontana
DOI:10.1039/c3ob40739j
日期:——
We have designed and synthesized two amphiphilic calix[6]arene derivatives, CA8 and CA18, that combine the potential to act as wheel components for pseudorotaxane structures with the self-assembly features typical of surfactant molecules in aqueous solution. Their endo-cavity recognition and self-aggregation properties were compared with those of a non-amphiphilic analogue, C8. TEM, DLS, and fluorescence experiments show that in water the amphiphilic calixarenes form vesicle- and micelle-like aggregates. The size, nature and properties of such aggregates depend on the length of the alkyl chain anchored at the lower rim of the calix[6]arene skeleton, as well as on the inclusion of a molecular guest into the wheel. Specifically, the release of a fluorescent guest entrapped inside the CA8 vesicles is accelerated in the presence of dioctylviologen axles that can pierce the calixarene cavity.
我们设计并合成了两种两性聚合物卡拉[6]芳烃衍生物CA8和CA18,它们结合了作为伪旋转结构轮部件的潜力,以及在水溶液中典型的表面活性剂分子的自组装特性。它们的内腔识别和自聚集特性与一种非两性类似物C8进行了比较。透射电子显微镜(TEM)、动态光散射(DLS)和荧光实验表明,在水中,这些两性卡拉芳烃形成类似囊泡和胶束的聚集体。这些聚集体的大小、性质和特性取决于锚定在卡拉[6]芳烃骨架下缘的烷基链的长度,以及分子客体的包含。具体而言,在存在可以穿透卡拉芳烃腔体的二辛基紫罗兰轴时,困在CA8囊泡内的荧光客体的释放被加速。