Beilstein Journal of Organic Chemistry 2015-01-01

Tetrathiafulvalene-based azine ligands for anion and metal cation coordination.

Awatef Ayadi, Aziz El Alamy, Olivier Alévêque, Magali Allain, Nabil Zouari, Mohammed Bouachrine, Abdelkrim El-Ghayoury

Index: Beilstein J. Org. Chem. 11 , 1379-91, (2015)

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Abstract

The synthesis and full characterization of two tetrathiafulvalene-appended azine ligands, namely 2-([2,2'-bi(1,3-dithiolylidene)]-4-yl)-6-((2,4-dinitrophenyl)hydrazono)methyl)pyridine (L1) and 5-([2,2'-bi(1,3-dithiolylidene)]-4-yl)-2-((2,4-dinitrophenyl)hydrazono)methyl)pyridine (L2) are described. The crystal structure of ligand L1 indicates that the ligand is completely planar with the presence of a strong intramolecular N3-H3···O1 hydrogen bonding. Titration experiments with inorganic anions showed that both ligands are suitable candidates for the sensing of fluoride anions. Ligand L2 was reacted with a Re(I) cation to yield the corresponding rhenium tricarbonyl complex 3. In the crystal structure of the newly prepared electroactive rhenium complex the TTF is neutral and the rhenium cation is hexacoordinated. The electrochemical behavior of the three compounds indicates that they are promising for the construction of crystalline radical cation salts.