The hydrogenation of calix[4]pyrroles leading to the novel ligand system calix[4]pyrrolidine: Their properties and their application
| Responsable du projet | Reinhard Neier |
| Collaborateur |
Helen Stoeckli Evans
Invernizzi Christian Prodea Anca |
| Résumé |
"Let's get practical". With these words George Whitesides
and John Deutch are launching an appeal to to rethink the future of
chemistry in the 21st century (Nature, 2011, Vol. 469, p. 21-22). To
solve the challenges of the 21th century chemistry will have to
concentrate on solving problems of importance to our societies.
Our group is concentrating on the bio-inspired approach to novel
macrocyclic ligand systems. The prototypical metal complexes of
natural macrocycles fullfill vital tasks, such as photochemical
energy production, energy storage through redox processes and the
transport and use of oxygen. The simple and efficient synthesis of
calix[4]pyrrole has been known for more than 125 years. The
connectivity of these heterocyclic calix[4]arenes is identical with
the skeleton of the "pigments of life". Despite this
ressemblence of the connectivity graph, the chemical properties of
the porphyrin derived natural "pigments of life" and the
synthetic calix[4]pyrroles are completely different. The
"pigments of life" are almost ideal ligands and form
metal complexes with great ease. The function of the indivudual
"pigment of life" depends on the metal but also in a
subtle way on the ligand and finally on the second coordination
sphere. The goal of our research project is to make use of the
efficient access to the calix[4]pyrrole skeleton and to transform
these compounds into excellent ligands by a "simple"
hydrogenation step. We have reported proof-of-principle results by
isolating and characterizing the totally reduced
calix[4]pyrrolidine. The great challenge is to make the access to
this novel macrocyclic structure efficient and experimentally
easy. |
| Mots-clés |
Calix[4]pyrrole, Macrocyclic Ligands, Pyrrole, Stereochemistry, Hydrogenation, Heterogenous, Organocatalysis |
| Type de projet | Recherche fondamentale |
| Domaine de recherche | Chimie organique |
| Source de financement | FNS - Encouragement de projets (Div. I-III) |
| Etat | Terminé |
| Début de projet | 1-4-2012 |
| Fin du projet | 31-12-2015 |
| Budget alloué | 200'000.00 |
| Autre information |
http://p3.snf.ch/projects-140555# |
| Contact | Reinhard Neier |