Tricyclic octaurea "Temples" for the recognition of polar molecules in water.
Tricyclic octaurea "Temples" for the recognition of polar molecules in water.
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三环八脲“寺庙”用于识别水中的极性分子。
DOI：
10.1039/d2ob02061k
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发表时间：
2023
影响因子：
3.2
通讯作者：
Webster CS
中科院分区：
文献类型：
--
作者：
Webster CS
两个水溶性三环“寺”大环具有芘屋顶/地板单元和双脲间隔已被合成和研究作为受体的芳香族化合物在水介质中。三环对甲基化嘌呤生物碱如咖啡因相对于未取代的杂环如腺嘌呤和吲哚显示出良好的选择性。结合的信号是荧光的主要变化，显然是由于分子内准分子的分裂。准分子的形成意味着在没有客人的情况下空腔崩溃，这解释了为什么与早期的亲戚不同，这些受体不结合碳水化合物。萘二酰亚胺（NDI）也被研究为几何互补客体，并且确实结合特别强（Ka > 107 M−1）;这种强大的选择性缔合暗示了在超分子自组装中的潜在应用。
Two water-soluble tricyclic “Temple” macrocycles featuring pyrene roof/floor units and bis-urea spacers have been synthesised and studied as receptors for aromatic compounds in aqueous media. The tricycles show good selectivity for methylated purine alkaloids such as caffeine versus unsubstituted heterocycles such as adenine and indole. Binding is signalled by major changes in fluorescence, apparently due to the break-up of intramolecular excimers. The formation of excimers implies cavity collapse in the absence of guests explaining why, unlike an earlier relative, these receptors do not bind carbohydrates. Naphthalenediimides (NDIs) have also been studied as geometrically complementary guests, and indeed bind especially strongly (Ka > 107 M−1); this powerful and selective association suggests potential applications in supramolecular self-assembly.