6-Nitro-[1,10]phenanthroline-1-ium nitrate: crystal structure, ab initio calculations and protonation character

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 (Ni2+, Zn2+, Cd2+, and Fe2+) 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.

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Tetrathiafulvalene‐Based Phenanthroline Ligands: Synthesis, Crystal Structures, and Electronic Properties

Belhadj

El‐Ghayoury

Cauchy

et al. 2014

Eur J Inorg Chem

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Theoretical and experimental study of the protonated 2,4,6-tri(2-pyridyl)-1,3,5-triazine [TPTZH2]2+

et al. 2013

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The reaction between 2,4,6-tri(2-pyridyl)-1,3,5-triazine (TPTZ) and sulfuric acid in the presence of NH 4 PF 6 yielded crystals of [TPTZH 2 ](PF 6 ) 2 ÁH 2 O, characterized by spectroscopic methods and single-crystal X-ray diffraction. The structural data indicate that the diprotonated form, [TPTZH 2 ] 2? , is more planar than the neutral TPTZ molecule. Due to the presence of PF 6 anions located between neighboring dications, the triazine and/or pyridyl rings in each dication cannot interact in a p-p fashion. The proton affinity of TPTZ was computed using density function theory (B3LYP hybrid functional). Calculated thermochemical results and proton affinities indicate that for the first protonation, the favorable N atoms are different from those obtained from calculations based on Merz-Kollman atomic charges. For the second protonation, the proton affinities show a clear preference of the protonation on two N atoms, this time not contradicted by Merz-Kollman atomic charges, and in agreement with the experimental data. In the UV-Vis spectrum, two visible absorption bands of [TPTZH 2 ](PF 6 ) 2 ÁH 2 O are most likely arising from an outer-sphere charge-transfer. The photoluminescence properties of TPTZ and [TPTZH 2 ](PF 6 ) 2 were studied at room temperature in CH 3 CN solution.

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4-(3-Carboxyphenyl)pyridinium nitrate

Tang

et al. 2012

Acta Cryst E

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In the title salt, C12H10NO2 +·NO3 −, the dihedral angle between the pyridine ring and the benzene ring of the 4-(3-carboxyphenyl)pyridinium cation is 30.14 (2)°. Inversion-related pairs of cations are linked into dimers by pairs of O—H⋯O hydrogen bonds. Pairs of dimers are linked by N—H⋯O and C—H⋯O hydrogen bonds involving nitrate anions as acceptors, generating supramolecular chains along the diagonal of the bc plane.

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6-Nitro-[1,10]phenanthroline-1-ium nitrate: crystal structure, ab initio calculations and protonation character

Cited by 3 publications

References 23 publications

Tetrathiafulvalene‐Based Phenanthroline Ligands: Synthesis, Crystal Structures, and Electronic Properties

Tetrathiafulvalene‐Based Phenanthroline Ligands: Synthesis, Crystal Structures, and Electronic Properties

Theoretical and experimental study of the protonated 2,4,6-tri(2-pyridyl)-1,3,5-triazine [TPTZH2]2+

4-(3-Carboxyphenyl)pyridinium nitrate

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