New Synthetic Route to Water‐Soluble Prism[5]arene Hosts and Their Molecular Recognition Properties**
New Synthetic Route to Water‐Soluble Prism[5]arene Hosts and Their Molecular Recognition Properties**
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水的新合成路线——可溶棱柱[5]芳烃主体及其分子识别特性**
DOI：
10.1002/chem.202201743
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Isaacs, Lyle
中科院分区：
文献类型：
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作者：
Zhai, Canjia;Isaacs, Lyle
我们报道了带有乙酯官能团的萘单体的直接大环化产生棱柱[5]芳烃衍生物，其可以脱保护产生水溶性棱柱[5]芳烃（H1和H3）。1H NMR光谱表明，双阳离子客体与埋在各向异性磁屏蔽腔中的疏水核结合。 等温滴定量热法测量表明，H1和H3在PBS缓冲水中是高亲和力的主体，对于选定的客体，Ka值超过109 M − 1。络合事件由非经典疏水效应、CH π相互作用和静电相互作用驱动。H1和H3在化学和生物学应用中应与其他高亲和性主体一起考虑。
We report that the direct macrocyclization of naphthalene monomers bearing ethyl ester functional groups delivers prism[5]arene derivatives, which can be deprotected to yield water‐soluble prism[5]arenes (H1andH3).1H NMR spectroscopy showed that dicationic guests bind with the hydrophobic cores buried inside the anisotropic magnetically shielding cavity. Isothermal titration calorimetry measurements showed thatH1andH3are high‐affinity hosts in PBS‐buffered water with Kavalues exceeding 109M−1for a select guest. The complexation events are driven by the non‐classical hydrophobic effect, CH⋅⋅⋅π interactions, and electrostatic interactions. HostH1displays somewhat higher affinity toward a common guest than pillar[6]arene bearing carboxylic acid functional groups but is significantly less potent than pillar[6]arene bearing sulfate groups.H1andH3should be considered alongside other high affinity hosts for a variety of chemical and biological applications.