Efficiency of Dinucleosides as the Backbone to Pre-Organize Multi-Porphyrins and Enhance Their Stability as Sandwich Type Complexes with DABCO
Sonja Merkaš,
Souhaila Bouatra,
Régis Rein,
Ivo Piantanida,
Mladen Zinic,
Nathalie Solladié
Affiliations
Sonja Merkaš
CNRS, LCC (Laboratoire de Chimie de Coordination), 205 Route de Narbonne, 31077 Toulouse France and Université de Toulouse, UPS, INPT, 31077 Toulouse, France
Souhaila Bouatra
CNRS, LCC (Laboratoire de Chimie de Coordination), 205 Route de Narbonne, 31077 Toulouse France and Université de Toulouse, UPS, INPT, 31077 Toulouse, France
Régis Rein
CNRS, LCC (Laboratoire de Chimie de Coordination), 205 Route de Narbonne, 31077 Toulouse France and Université de Toulouse, UPS, INPT, 31077 Toulouse, France
Ivo Piantanida
Laboratory of Supramolecular and Nucleoside Chemistry, Rudjer Boskovic Institute, Bijenicka cesta 54, HR-10002 Zagreb, Croatia
Mladen Zinic
Laboratory of Supramolecular and Nucleoside Chemistry, Rudjer Boskovic Institute, Bijenicka cesta 54, HR-10002 Zagreb, Croatia
Nathalie Solladié
CNRS, LCC (Laboratoire de Chimie de Coordination), 205 Route de Narbonne, 31077 Toulouse France and Université de Toulouse, UPS, INPT, 31077 Toulouse, France
Flexible linkers such as uridine or 2′-deoxyuridine pre-organize bis-porphyrins in a face-to-face conformation, thus forming stable sandwich complexes with a bidentate base such as 1,4-diazabicyclo[2.2.2]octane (DABCO). Increased stability can be even greater when a dinucleotide linker is used. Such pre-organization increases the association constant by one to two orders of magnitude when compared to the association constant of DABCO with a reference porphyrin. Comparison with rigid tweezers shows a better efficiency of nucleosidic dimers. Thus, the choice of rigid spacers is not the only way to pre-organize bis-porphyrins, and well-chosen nucleosidic linkers offer an interesting option for the synthesis of such devices.
