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Tetrathiafulvalene‐Based Phenanthroline Ligands: Synthesis, Crystal Structures, and Electronic Properties
Author(s) -
Belhadj Esmah,
ElGhayoury Abdelkrim,
Cauchy Thomas,
Allain Magali,
Mazari Miloud,
Sallé Marc
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201402073
Subject(s) - tetrathiafulvalene , cyclic voltammetry , chemistry , electrochemistry , absorption spectroscopy , phenanthroline , metal , crystal structure , metal ions in aqueous solution , single crystal , crystallography , absorption (acoustics) , inorganic chemistry , materials science , molecule , organic chemistry , electrode , physics , quantum mechanics , composite material
The synthesis and full characterization of three tetrathiafulvalene‐based phenanthroline ligands, namely, N ‐(1,10‐phenanthrol‐5‐yl)‐6,7‐(ethylenedithio)tetrathiafulvalene‐2‐carboxamide ( 1 ), 2‐[(1,10‐phenanthrol‐5‐yl)aminocarbonylmethylthio]‐3,6,7‐tris(methylsulfanyl)tetrathiafulvalene ( 2 ), and 2‐[(1,10‐phenanthrol‐5‐yl)iminomethyl]tetrathiafulvalene ( 3 ), are described. The electronic absorption properties and the electrochemical behavior of the three ligands have been studied. The UV/Vis absorption spectra of these compounds have been rationalized by time‐dependent DFT (TD‐DFT) calculations, and the single‐crystal X‐ray structures of 2 and 3 have been determined. The binding properties of these multifunctional systems for various transition metal ions (Ni 2+ , Zn 2+ , Cd 2+ , and Fe 2+ ) have been analyzed in solution by cyclic voltammetry and UV/Vis spectroscopy. The results show that these ligands are suitable candidates for the preparation of electroactive metal complexes and radical cation salts.