Annual Scientific Report 2014

Abstract

Our research is mainly focused on the design, synthesis and study of functional multimolecular aggregates. We are interested in the thermodynamic and kinetic characterization of the self-assembly processes that leads to their formation in solution. We are also involved in the study of the applications of unimolecular and supramolecular containers. We investigate the effect that the confinement of molecules and catalyst in nanoscopic spaces may have in the modification of their typical properties expressed in the bulk or free in solution. The group is also working on the synthesis of new calix pyrrole receptors and supramolecular capsules based on calix[4]pyrrole and/or calix arene scaffolds with the possibility to control their binding affinities and encapsulation properties using external stimuli i.e. light.

Another topic of our interest resides in the study and quantification of weak non-covalent interactions using synthetic receptors as new physical organic chemistry tools.

Topics addressed

• Porphyrins and tetraazaporphyrins
• Encapsulation of organometallic compounds
• Anion-π interactions
• New insights in calix[4]pyrrole receptors

Articles

“Single-Molecule-Magnet Behavior in the Family of [Ln(OETAP)₂] Double-Decker Complexes (Ln = Lanthanide, OETAP = Octa(ethyl)tetraazaporphyrin)”
Chem. Eur. J. (2014), 20, 12817-12825
N. Giménez-Agulló, C. Saenz de Pipaon, L. Adriaenssens, M. Filibian, M. Martinez-Belmonte, E.C. Escudero-Adan, P. Carretta, P. Ballester, J.R. Galan-Mascaros

“Binding of calix[4]pyrroles to pyridine N-oxides probed with surface plasmon resonance”
Chem. Sci. (2014), 5, 4210-4215
L. Adriaenssens, J.L. Acero Sanchez, X. Barril, C.K. O’Sullivan, P. Ballester

“Reversible photocontrolled disintegration of a dimeric tetraurea-calix[4]pyrrole capsule with all-trans appended azobenzene units”
Chem. Sci. (2014), 5, 4260-4264
L. Osorio-Planes, M. Espelt, M.A. Pericas, Pablo Ballester

“Pyridyl-Decorated Self-Folding Hepta-amide Cavitands as Ligands in the Rhodium-Catalyzed Hydrogenation of Norbornadiene”
Eur. J. Org. Chem. (2014), 4276-4282
S. Korom, P. Ballester

“Synthesis, Structure, and Binding Properties of Lipophilic Cavitands Based on a Calix[4]-pyrrole-Resorcinarene Hybrid Scaffold”
J. Org. Chem. (2014), 79, 5545-5557
A. Galan, E.C. Escudero-Adan, A. Frontera, P. Ballester

“Self-Sorting of Cyclic Peptide Homodimers into a Heterodimeric Assembly Featuring an Efficient Photoinduced Intramolecular Electron-Transfer Process”
Chem. Eur. J. (2014), 20, 3427-3438
G. Aragay, B. Ventura, A. Guerra, I. Pintre, C. Chiorboli, R. Garcia-Fandino, L. Flamigni, J.R. Granja, P. Ballester

“Supramolecular catalysis. Part 2: artificial enzyme mimics”
Chem. Soc. Rev. (2014), 43, 1734-1787
M. Raynal, P. Ballester, A. Vidal-Ferran, P.W.N.M. van Leeuwen

“Supramolecular catalysis. Part 1: non-covalent interactions as a tool for building and modifying homogeneous catalysts”
Chem. Soc. Rev. (2014), 43, 1660-1733
M. Raynal, P. Ballester, A. Vidal-Ferran, P.W.N.M. van Leeuwen

“Thermodynamic Characterization of Halide – -Π Interactions in Solution Using “Two-Wall” Aryl Extended Calix [4]pyrroles as Model System.
L. Adrianenssens, G. Gil-Ramírez, A. Frontera, D. Quiñonero, E. C. Escudero-Adán, P. Ballester. J. AM.
Chem. Soc., 2014, 136, 3208-3218

“Porphyrin tweezer receptors: Binding studies, conformational properties and applications.”
V. Valderrey, G. Aragay, P. Ballester.
Coor. Chem. Rev., 2014, 258-259, 137-156