The synthesis of monomeric pentacoordinated diorganotin complexes derived from pyridoxamine dihydrochloride and substituted salicylaldehydes is described. The complexes were characterized using UV/Vis, IR, MS, as well as 1 H, 13 C, and 119 Sn NMR techniques; the molecular structure of the 1e complex was established by X-ray diffraction, which showed a distorted trigonal bipyramidal geometry, in which the basal plane is defined by the butyl groups and the azomethine nitrogen atom, whereas the oxygen atoms from the aromatic ring occupy axial positions. The cytotoxic activity of the complexes against human cell lines U-251 (glioblastoma), PC-3 (prostate), K-562 (chronic myelogenous leukemia), HCT-15 (human colorectal), MCF-7 (human breast), SKLU-1 (non-small cell lung), and MDA-MB-251 (human breast) was evaluated, and the inhibitory percentage values indicated higher activities than the reference standard, cisplatin, and non-cytotoxic activity was observed in culture of mononuclear cells from peripheral blood on healthy Wistar rats. Oral toxicity studies were performed by the OECD test guide line 423 and reveals that LD 50 of complexes 1a, 1b, 1c-1g is in the range of 200-300 mg/Kg body weight and can be classified under category 3, the complexes 1c and 1h resulted to be the less toxic.
The synthesis of monomeric pentacoordinated diorganotin(IV) complexes derived from pyridoxal hydrochloride and 4-or 5-R-substituted ortho-aminophenols is described. The complexes were characterized using UV-visible, infrared, mass, 1 H NMR, 13 C NMR and 119 Sn NMR spectral techniques. The molecular structure of three complexes was established using X-ray diffraction: 3b and 3d show a distorted trigonal bipyramidal geometry, in which the basal plane is defined by the butyl groups and the iminic nitrogen atom, whereas the oxygen atoms from the aromatic ring occupy axial positions; in contrast, complex 3e exhibits a square pyramidal geometry. The cytotoxic activity of all complexes against human cell lines U-251 (glioblastoma), K-562 (chronic myelogenous leukemia), HCT-15 (human colorectal cancer), MCF-7 (human breast cancer) and SKLU-1 (non-small-cell lung cancer) was evaluated, and the inhibitory percentage values indicated higher activity than the reference standard, cisplatin. Acute toxicity studies were performed in vivo for the prepared complexes to determine the lethal medium dose (LD 50 ) after intraperitoneal administration to mice.
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.
This work refers to the manufacture and characterization of organic electronic devices made from seven-coordinated diorganotin(IV) complexes and the polymer poly(3,4-ethylenedyoxithiophene)-poly(styrene sulfonate) (PEDOT:PSS). In order to obtain the best electronic behavior, the devices were manufactured by spin-coating with seven-coordinated diorganotin(IV) complexes, synthetized with different peripheral substituents. The modification of the polarity in the molecule, from the presence of the different functional groups, is used as a way to enhance the charge transport inside the devices. Additionally, the devices received a post-treatment with isopropyl alcohol, in order to change the structure of PEDOT:PSS from benzoid form to quinoid form. The electric charge transport was evaluated from the current density–voltage characteristics, under dark and illuminated conditions. The devices present a mobility of ∼10−9 cm2/Vs decreasing to values of ∼10−11–10−10 cm2/Vs. They display a photocurrent of ∼10−7–10−8 A cm−2 and a reduction is observed after the treatment. It is mainly the presence of the peripheral substituents in the diorganotin(IV) complexes, and not the polymer structure, that causes the electrical behavior of the device. The films made from seven-coordinated diorganotin(IV) complex particles deposited on the PEDOT:PSS, as well as their post-treatment, were characterized by Raman, ultraviolet-vis spectroscopy, scanning electronic microscopy and atomic force microscopy.
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