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Molecules 2017, 22(7), 1112; doi:10.3390/molecules22071112

Efficiency of Dinucleosides as the Backbone to Pre-Organize Multi-Porphyrins and Enhance Their Stability as Sandwich Type Complexes with DABCO

1
CNRS, LCC (Laboratoire de Chimie de Coordination), 205 Route de Narbonne, 31077 Toulouse France and Université de Toulouse, UPS, INPT, 31077 Toulouse, France
2
Laboratory of Supramolecular and Nucleoside Chemistry, Rudjer Boskovic Institute, Bijenicka cesta 54, HR-10002 Zagreb, Croatia
Current Address: Novartis Pharma AG, CH-4056 Basel, Switzerland
*
Author to whom correspondence should be addressed.
Received: 10 April 2017 / Accepted: 28 June 2017 / Published: 6 July 2017
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Abstract

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. View Full-Text
Keywords: porphyrins; nucleosides; supramolecular complexes porphyrins; nucleosides; supramolecular complexes
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Merkaš, S.; Bouatra, S.; Rein, R.; Piantanida, I.; Zinic, M.; Solladié, N. Efficiency of Dinucleosides as the Backbone to Pre-Organize Multi-Porphyrins and Enhance Their Stability as Sandwich Type Complexes with DABCO. Molecules 2017, 22, 1112.

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