Cyclodextrin-templated porphyrin nanorings.
Cyclodextrin-templated porphyrin nanorings.
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DOI：
10.1002/anie.201402917
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发表时间：
2014-07-21
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α-和β-环糊精已经被用作合成六条和七条腿模板的支架，通过将每个初级CH2OH与4-吡啶基部分官能化。虽然这些模板是灵活的，但它们对于合成由六个或七个卟啉单元组成的大环卟啉低聚物非常有效。从核磁共振和圆二色谱可以看出，手性从环糊精模板转移到它们的纳米主体上。令人惊讶的是，在六卟啉纳米环内结合柔性α-环糊精模板的平均有效摩尔浓度(74m)几乎与先前研究的刚性六齿模板(180m)一样高。柔性模板在该系统中有效的发现，以及具有质数结合位点的模板的可获得性，为模板指导合成更大的大环开辟了许多可能性。
α- and β-Cyclodextrins have been used as scaffolds for the synthesis of six- and seven-legged templates by functionalizing every primary CH2OH with a 4-pyridyl moiety. Although these templates are flexible, they are very effective for directing the synthesis of macrocyclic porphyrin oligomers consisting of six or seven porphyrin units. The transfer of chirality from the cyclodextrin templates to their nanoring hosts is evident from NMR and circular dichroism spectroscopy. Surprisingly, the mean effective molarity for binding the flexible α-cyclodextrin-based template within the six-porphyrin nanoring (74 m) is almost as high as for the previously studied rigid hexadentate template (180 m). The discovery that flexible templates are effective in this system, and the availability of a template with a prime number of binding sites, open up many possibilities for the template-directed synthesis of larger macrocycles.