A series of new mono-1,2,3-triazole derivatives of pyrimidine nucleobases were synthesized by one-pot copper(I)-catalyzed 1,3-dipolar cycloaddition reactions between N-1-propargyluracil and thymine, sodium azide and several benzyl halides. The desired heterocyclic compounds were obtained in good yields and characterized by NMR, IR, and high resolution mass spectrometry. These compounds were investigated as corrosion inhibitors for steel in 1 M HCl solution, using electrochemical impedance spectroscopy (EIS) technique. The results indicate that these heterocyclic compounds are promising acidic corrosion inhibitors for steel.
Four organotin compounds bearing Schiff bases were prepared via a multicomponent microwave-assisted reaction among 2-hydroxy-1-naphthaldehyde, 2-aminophenol derivatives and the corresponding diorganotin oxide (R2SnO, R = nBu or Ph), with high yields and a low economic/environmental impact. All of the compounds were fully characterized by NMR (1H, 13C, and 119Sn) spectroscopy, high-resolution mass spectrometry, X-ray diffraction, cyclic voltammetry, UV/Vis spectroscopy, and fluorescence spectroscopy. All of the compounds absorb in the visible region around 480–490 nm, close to the maximum solar emission, with an optical band gap of around 2.3 eV and low fluorescence quantum yields. According to the electrochemical study, they present LUMO values close to that of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM-C60), a typical electron acceptor organic photovoltaic material. Based on this combined optical/electrochemical study and as it allows the preparation of homogeneous spun films, the n-butyltin complex with carboxylic acid was selected for the investigation of its possible photovoltaic properties in organic solar cells. Charge photogeneration was obtained only using this organotin compound as an electron acceptor material with poly(3-hexylthiophene, P3HT) (typical electron donor material) with an open circuit voltage of 300 mV, a short-circuit current density of 0.11 mA cm−2 and an efficiency of 5.2 × 10−3%. Despite the fact that the efficiency is much lower with respect to the reference device P3HT/PCBM-C60, this preliminary result suggests that, after chemical and device processing optimization, tin complexes with Schiff bases could be applied as electron acceptor materials in organic photovoltaic devices.
An efficient one-pot synthesis of 1,2,3-triazole derivatives of dihydropyrimidinones has been developed using two multicomponent reactions. The aldehyde-1,2,3-triazoles were obtained in good yields from in situ-generated organic azides and O-propargylbenzaldehyde. The target heterocycles were synthesized through the Biginelli reaction in which the aldehyde-1,2,3-triazoles reacted with ethyl acetoacetate and urea in the presence of Ce(OTf)3 as the catalyst. The corrosion inhibition of steel grade API 5 L X52 in 1 M HCl by the synthesized compounds was investigated using the electrochemical impedance spectroscopy technique. The measurements revealed that these heterocycles are promising candidates to inhibit acidic corrosion of steel.
Ten 1,4-disubstituted 1,2,3-triazoles were synthesized from one of 1-(azido-methyl)benzene, 1-(azidomethyl)-4-fluorobenzene, 1-(azidomethyl)-4-chlorobenzene, 1-(azidomethyl)-4-bromobenzene or 1-(azidomethyl)-4-iodobenzene, generated in situ from sodium azide and the corresponding benzyl halide, and dipropargyl uracil or dipropargyl thymine. Optimal experimental conditions were established for the conventional click chemistry. The corrosion inhibiting properties of some of these compounds, which were determined by means of an electrochemical technique, are also presented.