Synthesis and self-assembly processes of monofunctionalized cucurbit[7]uril.
Synthesis and self-assembly processes of monofunctionalized cucurbit[7]uril.
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DOI：
10.1021/ja3058502
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发表时间：
2012-08-08
影响因子：
15
通讯作者：
Isaacs L
中科院分区：
文献类型：
--
作者：
Vinciguerra B;Cao L;Cannon JR;Zavalij PY;Fenselau C;Isaacs L
我们提出了一种构建块方法，通过亚甲基桥接糖脲六聚体1和糖脲二（环醚）2和12的缩合来实现功能化CB[7]衍生物。CB[7]衍生物Me2CB[7]和CyCB[7]具有高水溶性（分别为264 mM和181 mM）。由于Me2CB[7]的高固有溶解度，它能够溶解不溶性的苯并咪唑类药物阿苯达唑。六聚体1与含一个伯烷基氯基的乙二醇酰衍生物12反应得到cb[7]衍生物18，分离产率为16%。化合物18与NaN3反应生成叠氮化物取代的CB[7]9，收率为81%，随后与丙基氯化铵（21）发生咔嗒反应，生成CB[7]衍生物20，收率为95%，在其赤道上带有共价的三唑基铵。核磁共振波谱（1H，变温，DOSY）和电喷雾质谱的结果证实了20在水溶液中自组装形成环四聚体（204）。含活性官能团（如N3， Cl）的CB[7]衍生物现在可用于纳入更复杂的功能体系。
We present a building block approach toward functionalized CB[7] derivatives by the condensation of methylene bridged glycoluril hexamer 1 and glycoluril bis(cyclic ethers) 2 and 12. The CB[7] derivatives Me2CB[7] and CyCB[7] are highly soluble in water (264 mM and 181 mM, respectively). As a result of the high intrinsic solubility of Me2CB[7], it is able to solubilize the insoluble benzimidazole drug albendazole. The reaction of hexamer 1 with glycoluril derivative 12 which bears a primary alkyl chloride group gives CB[7] derivative 18 in 16% isolated yield. Compound 18 reacts with NaN3 to yield azide-substituted CB[7] 19 in 81% yield which subsequently undergoes click reaction with propargylammonium chloride (21) to yield CB[7] derivative 20 in 95% yield which bears a covalently attached triazolyl ammonium group along its equator. The results of NMR spectroscopy (1H, variable temperature, and DOSY) and electrospray mass spectrometry establish that 20 undergoes self-assembly to form the cyclic tetrameric assembly (204) in aqueous solution. CB[7] derivatives bearing reactive functional groups (e.g. N3, Cl) are now available for incorporation into more complex functional systems.
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影响因子：
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作者：
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DOI：
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