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.
Highlights
Tetrathiafulvalene (TTF) is known to have excellent electrondonating properties resulting in stable radical cation (TTF+) and dication (TTF2+) species from two sequential and reversible oxidation processes
The protocol followed for the synthesis of the new azine ligands L1 and L2 is summarized in Scheme 2
Ligand L2 exhibit a strong electronic conjugation between the donor and the acceptor resulting in the occurrence of an intramolecular charge transfer (ICT) band between the two fragments
Summary
Tetrathiafulvalene (TTF) is known to have excellent electrondonating properties resulting in stable radical cation (TTF+) and dication (TTF2+) species from two sequential and reversible oxidation processes. We report the synthesis and electronic properties of two new multifunctional TTF-based azine ligands that integrate distinctive functional groups as depicted in Scheme 1 and capable of coordinating both metal cations as well as inorganic anions.
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