Proton transfer complexes based on some π-acceptors having acidic protons with 3-amino-6-[2-(2-thienyl)vinyl]-1,2,4-triazin-5(4H)-one donor: Synthesis and spectroscopic characterizations

Charge transfer complexes based on 3-amino-6-[2-(2-thienyl)vinyl]-1,2,4-triazin-5(4H)-one (ArNH2) organic basic donor and pi-acceptors having acidic protons such as picric acid (PiA), hydroquinone (Q(OH)2) and 3,5-dinitrobenzene (DNB) have been synthesized and spectroscopically studied. The NH3+ ammonium ion was formed under the acid–base theory through proton transfer from an acidic to basic centers in all charge transfer complexes resulted. The values of formation constant (KCT) and molar extinction coefficient (εCT) which were estimated from the spectrophotometric studies have a dramatic effect for the charge transfer complexes with differentiation of pi-acceptors. For further studies the vibrational spectroscopy of the [(ArNH3+)(PiA–)] (1), [(ArNH3+)(Q(OH)2-)] (2) and [(ArNH3+)(DNB–)] (3) of (1:1) charge transfer complexes of (donor: acceptor) were characterized by elemental analysis, infrared spectra, Raman spectra, 1H and 13CNMR spectra. The experimental data of elemental analyses of the charge transfer complexes (1), (2) and (3) were in agreement with calculated data. The IR and Raman spectra of (1), (2) and (3) are indicated to the presence of bands around 3100 and 1600 cm–1 distinguish to NH3+. The thermogravimetric analysis (TG) and differential scanning calorimetry (DSC) techniques were performed to give knowledge about thermal stability behavior of the synthesized charge transfer complexes. The morphological features of start materials and charge transfer complexes were investigated using scanning electron microscopy (SEM) and optical microscopy.

► In this study we examine three new charge complexes under acid–base theory. ► The values of formation constant (KCT) and molar extinction coefficient (εCT) which were estimated. ► In this study we used various spectroscopic and thermal analyses. ► The morphological features of start materials and charge transfer complexes were investigated.