Tin(IV) complexes 2a—q derived from pyridine Schiff bases were prepared and characterized. Four complexes of this series were evaluated in vitro against different carcinogenic cell lines; besides their anti-inflammatory and antioxidant properties were also tested. Combination of mass spectrometry, multinuclear NMR and X-ray diffraction techniques evidenced the formation of heptacoordinated monomeric species. The X-ray diffraction analysis of 2a, 2b, 2i, 2j and 2n led to establish the heptacoordination around the tin atom in solid state and also revealed that the ligand occupies the equatorial positions of the distorted pentagonal bipyramidal geometry and the two alkyl or aryl groups the axial positions. The in-vitro study for complexes 2a—d against six tumor cell lines showed varied antiproliferative activity, the IC50 for all tested complexes was lower than that of the cis-platin. Compounds 2a—d also exhibited anti-inflammatory activity where complex 2c resulted to be more active (IC50=0.11 μM) than the indomethacin IC50=0.27 μM which was used as reference. The antioxidant activity in rat brain homogenate on inhibition of thiobarbituric acid reactive substances (TBARS) indicated that 2c (IC50=1.77 μM) is more active than the quercetine (4.11 μM) and α-tocopherol (IC50=569.09 μM).
1 June 1999 in Journal of Organometallic Chemistry
The synthesis of four mononuclear heptacoordinated organotin (IV) complexes of mixed ligands derived from tridentated Schiff bases and pyrazinecarboxylic acid is reported. This organotin (IV) complexes were prepared by using a multicomponent reaction, the reaction proceeds in moderate to good yields (64% to 82%). The complexes were characterized by UV-vis spectroscopy, IR spectroscopy, mass spectrometry, 1H, 13C, and 119Sn nuclear magnetic resonance (NMR) and elemental analysis. The spectroscopic analysis revealed that the tin atom is seven-coordinate in solution and that the carboxyl group acts as monodentate ligand. To determine the effect of the substituent on the optoelectronic properties of the organotin (IV) complexes, thin films were deposited, and the optical bandgap was obtained. A bandgap between 1.88 and 1.98 eV for the pellets and between 1.23 and 1.40 eV for the thin films was obtained. Later, different types of optoelectronic devices with architecture “contacts up/base down” were manufactured and analyzed to compare their electrical behavior. The design was intended to generate a composite based on the synthetized heptacoordinated organotin (IV) complexes embedded on the poly(3,4-ethylenedyoxithiophene)-poly(styrene sulfonate) (PEDOT:PSS). A Schottky curve at low voltages (<1.5 mV) and a current density variation of as much as ~3 × 10−5 A/cm2 at ~1.1 mV was observed. A generated photocurrent was of approximately 10−7 A and a photoconductivity between 4 × 10−9 and 7 × 10−9 S/cm for all the manufactured structures. The structural modifications on organotin (IV) complexes were focused on the electronic nature of the substituents and their ability to contribute to the electronic delocalization via the π system. The presence of the methyl group, a modest electron donor, or the non-substitution on the aromatic ring, has a reduced effect on the electronic properties of the molecule. However, a strong effect in the electronic properties of the material can be inferred from the presence of electron-withdrawing substituents like chlorine, able to reduce the gap energies.