Development of flexible cavitand receptors based on calix[5]arene. Rational design, synthesis and study of their properties

Álvarez Yebra, Rubén
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Cavitands are macromolecules with a permanent cavity where smaller molecules or ions can be accommodated. The hydrophobic cavity of these supramolecules allows the binding of other molecules though non-covalent interactions, resulting in host-guest complexation. This behavior is very similar to the one that enzymes have toward their substrates, and for this reason cavitands are considered good candidates for biological mimesis. The most common and studied cavitands are the derivatives of resorcin[4]arene. Some of these cavitands present the ability to self-fold into a stabilized closed conformation that defines a deep cavity, through an intramolecular hydrogen bond network. Having proven useful in countless applications and a wide range of fields, such as molecular recognition or biomimetic and supramolecular catalysis, resorcin[4]arene cavitands have been presented as the pinnacle of this discipline. Nevertheless, our research group has identified some limitations of this scaffold. First, resorcin[4]arene cavitands have a reduced volume, limiting the variety of viable guests to small molecules or ions of lesser relevance. And second and most remarkable, these cavitands have high structural rigidity, lacking the ability to adapt to bound guests and hence hindering the applications inspired on biological systems. Due to these disadvantages, we have conceived a completely new family of cavitands based on calixarene macrocycles with expanded and flexible cavities, featuring self-¬folding properties and genuine induced fit behavior. This new approach promises to enable the development of applications with a more diverse and significant variety of guests and/or substrates. The main goals set within the context of this thesis were the development of a novel self--folding family of receptors with expanded and flexible binding sites, and the consolidation of the basis for the diversification of the structure in order to access a variety of features and characteristics within the same scaffold ​
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