An asymmetric TTF derivative bearing a phenyl β-diketone group as an efficient ligand towards functional materials

Abstract

A novel asymmetric tetrathiafulvalene (TTF) derivative bearing a conjugated phenyl β-diketone moiety 1-(4-tetrathiafulvalyphenyl)-4,4,4-trifluorobutane-1,3-dione (TTF-ph-tfacH) has been synthesized using feasible methods and fully characterized. The chelating ability of its enolate anion (TTF-ph-tfac) has been investigated with [M^IICl₂·xH₂O] (M = Zn and Co) leading to complexes [Zn(TTF-ph-tfac)₂(CH₃OH)₂] (2a) and [Co(TTF-ph-tfac)₂(CH₃OH)₂] (2b), where the metal center is coordinated with two TTF-ph-tfac ligands and two methanol molecules. This redox active ligand shows promising features for the elaboration of hybrid organic–inorganic building blocks. The magnetic analysis for 2b reveals very weak antiferromagnetic interactions between spin centers, which would be a precursor for magnetic conductors. The herein reported mono-substituted TTF derivative interconnected via the phenyl group, which is of extended conjugation, enhanced planarity, and asymmetric geometry, shows a great promise to multifunctional (conducting, non-linear optical, and magnetic) materials.