Compounds 1 and 2 (Figure 1, Section 8.1) were designed so that they will self-assemble into molecular tubes. This architecture has never before been constructed by small organic units and might lead to materials with new properties.
A double 1,3-dipolar cycloaddition of tert-butylnitrile oxide to the known dienes 3 (Scheme 1, Section 8.1) will be followed unmasking of the B-ketoester functionality embedded in the resulting isoxazole rings. Subsequent condensation with urea will furnish the target compounds. Due to their central bicyclic ring, compounds 1 and 2 will have a puckered molecular shape. The peripheral heterocycles ha the ability to form a two dimensional network of hydrogen bonds. These designed structural features could lead to the se assembly of nanotubes (Figure 2, Section 8.1). The exact conditions (for example, presence or absence of solvent, polarity the medium, additives) under which this phenomenon could take place will be determined.
Training content (objective, benefit and expected impact)
The applicant will become familiar with the techniques and methods used in the study of supramolecular ensembles. Thus, will be able to apply his synthetic skills in the preparation of designed materials with new properties (optical, electrochemical etc.).
Links with industry / industrial relevance (22)
This proposal has no links with industry or any industrial relevance.