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In recent years the interest in shape-persistent organic cage compounds has steadily increased, not at least, because dynamic covalent bond formations made such structures more easily available in high to excellent yields. One often used type of dynamic bond formation is that of an aldehyde and an amine to the resulting imine bond. Although the reversibility of the imine bond formation is advantageous for the high yields, it is at the same time disadvantageous for the compounds chemical stability. In contrast to imine bonds, amide bonds are much more robust. Unfortunately, till date, shape-persistent amide cages have been made by irreversible amide bond formations in multiple steps, very often accompanied by low overall yields. Here, we present a short approach to shape-persistent amide cages, exploiting the high-yielding reversible cage formation in the first step, followed by a Pinnick oxidation to the amide cages in the second. These chemically robust amide cage can be further transformed by bromination or nitration allowing to post-functionalize these in high yields. The impact of the substituents on gas sorption behavior was investigated.
This article was published in the following journal.
Name: Angewandte Chemie (International ed. in English)
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