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Tuning of Knoevenagel-type substrate reactivity and optical properties<br />
by supramolecular interactions<br />
Nadine Allendörfer & Jean-Marie Lehn*<br />
<strong>Laboratoire</strong> de Chimie Supramoléculaire, ISIS<br />
Université de Strasbourg<br />
8 Allée Gaspard Monge, 67000 Strasbourg (France)<br />
lehn@isis.u-strasbg.fr<br />
Dynamic chemistry uses reversible reactions of molecular and supramolecular entities.<br />
Here a covalent or non-covalent linkage of the components is possible. Dynamic<br />
covalent chemistry (DCC) has become a useful tool in material science and drug design.<br />
Some examples of reversible reactions used in DCC are amine/carbonyl condensations,<br />
peptide exchange, disulfide exchange, trans-esterifications, Diels-Alder condensations<br />
and olefin metathesis. In this work, we have focused on the Knoevenagel reaction,<br />
which allows the dynamic formation and cleavage of C=C double bonds.<br />
The reactivity of Knoevenagel-type substrates like benzylidenes, derived from<br />
aldehydes and barbituric acid, can be influenced by their structure. Therefore, we<br />
modified the aldehyde components to obtain polyene benzylidenes. Such donor-<br />
acceptor polyenes have interesting linear and nonlinear optical properties and have<br />
potential applications in telecommunications, optical data storage, and optical<br />
information processing.<br />
The reactivity and optical properties of Knoevenagel-type components can also be tuned<br />
by supramolecular interactions. An H-bond-mediated molecular recognition of various<br />
benzylidenes and receptors is observed. A comparative study of the reactivity and<br />
optical properties of Knoevenagel-type substrates with and without supramolecular<br />
influence was made.