Abstract
The selective functionalization of macrocyclic receptors remains extremely challenging because it generally requires the transformation of one and only one functional group among several identical groups. Recently, some of us described that the host-guest properties of a calix[6]arene-based Zn complex could be exploited for its selective monofunctionalization. Herein, we report on the extension of this synthetic strategy to a calix[6]arene-based receptor displaying a different recognition pattern with its guest. More precisely, a calix[6]arene tris-carboxylic acid-based receptor bearing three azido groups at the large rim was selectively monofunctionalized through an intramol. thermal Huisgen reaction with a hexynNH3+ ion accommodated into the cavity. This work shows that the monofunctionalization methodol. can also be performed efficiently with host-guest systems involving ionic/H-bonding interactions, and it is thus not limited only to the use of metal-ligand interactions. In other words, this supramol. methodol. can be used as a general tool for the selective functionalization of mol. receptors. [on SciFinder(R)]
Original language | English |
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Pages (from-to) | 1913-1919 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 79 |
Issue number | 5 |
DOIs | |
Publication status | Published - 2014 |
Externally published | Yes |
Keywords
- calixarene carboxylic acid receptor mol recognition hexynylammonium ion
- monofunctionalization thermal Huisgen cycloaddn azide contg receptor complexed alkyne