Kaya, İsmet; Bayır, Erdal; Solmaz, Adnan

In this study, the Schiff base 3-((2-phenylhydrazono)methyl)benzene-1,2-diol (3-PHMB) was synthesized through a condensation reaction between 2,3-dihydroxybenzaldehyde (2,3-DHBA) and phenylhydrazine (PH). The obtained Schiff base was subsequently subjected to oxidative polymerization in a 10% KOH (w/v) aqueous medium using hydrogen peroxide (35% H₂O₂), sodium hypochlorite (6–14% NaOCl), and oxygen (O₂) as oxidants, yielding the oligomers o-(3-PHMB)-P, o-(3-PHMB)-H, and o-(3-PHMB)-O. The structural, morphological, thermal, optical, and electrochemical characteristics of the synthesized compounds were comprehensively investigated using FT-IR, NMR, SEM, TG-DTA, UV-Vis, CV, and GPC techniques. UV-Vis and CV analyses revealed that the optical band gaps (Eg) were 2.33 eV for 3-PHMB, 2.06 eV for o-(3-PHMB)-P, 2.16 eV for o-(3-PHMB)-H, and 2.02 eV for o-(3-PHMB)-O, while the electrochemical band gaps (Eg′) were calculated as 2.03 eV, 1.65 eV, 1.63 eV, and 1.50 eV, respectively. Thermal analysis showed that the char yields at 1000 °C were 41.43% for o-(3-PHMB)-P, 38.72% for o-(3-PHMB)-H, and 44.35% for o-(3-PHMB)-O. Dielectric measurements indicated that o-(3-PHMB)-O exhibited higher polarization capacity and energy storage ability compared to the other oligomers. Moreover, the electrical conductivity values increased steadily with frequency; at 100 kHz, the conductivity was recorded as 1.74 × 10⁻⁵ S cm⁻¹ for o-(3-PHMB)-O and 1.64 × 10⁻⁵ S cm⁻¹ for o-(3-PHMB)-P. These findings demonstrate that the synthesized Schiff base oligomers are promising candidates for dielectric and optoelectronic applications due to their high thermal stability, controlled molecular weight distribution, and semiconducting properties.

İncele

Bayır, Erdal; Solmaz, Adnan; Kaya, İsmet; Yağmur, Hatice Karaer

In this study, 4-((2-phenylhydrazono)methyl)benzene-1,2-diol (4-PHBD) Schiff base was obtained from the condensation reaction between 3,4-dihydroxybenzaldehyde (3,4-DHBA) and phenylhydrazine (PH). The obtained Schiff base (4-PHBD) was polymerized using H2O2, NaOCl, and O2 oxidants in an aqueous basic medium (10 % KOH) and 4-PHBD was converted to o-(4-PHBD)-P (by H2O2 oxidant), o-(4-PHBD)-H (by NaOCl oxidant) and o-(4-PHBD)-O (by O2 oxidant). The structures of Schiff base and oligomers were characterized with FT-IR, NMR, SEM, TGA, UV-Vis, CV and GPC measurements. The Cyclic Voltammetry and UV-Vis measurements were used to ascertain the compounds' optical (Eg) and electrochemical (Eg’) band gaps, respectively. The Eg values of o-(4-PHBD)-P, o-(4-PHBD)-O and o-(4-PHBD)-H were found be 2.99, 2.63 and 3.26 eV, respectively. o-(4-PHBD)-O was used as an adsorbent in the removal of methylene green (MG) from an aqueous solution. The obtained data were applied to pseudo-first order and pseudo-second order kinetic models. It was determined that the adsorption process obeyed the pseudo first order kinetic model. The kinetic model was validated with R2, RMSE, SSE, SD, Δqe (%), MSE and ARE validation methods. The activation energy (Ea) was calculated as 7.31 kJ mol−1 using the Arrhenius equation. It was determined that the adsorption of MG on o-(4-PHBD)-O was physical adsorption.

AtıfScopus4·WoS4·OpenAlex3

İncele

Solmaz, Adnan; Kaya, İsmet; Bayır, Erdal

In this study, the 2-PHMBD Schiff base, synthesized through the condensation of 2,4-dihydroxybenzaldehyde (2,4-DHBA) with phenylhydrazine (PH), was subjected to oxidative polymerization in a basic medium using hydrogen peroxide (H2O2), sodium hypochlorite (NaOCl), and molecular oxygen (O2) as oxidizing agents. Three oligomers, designated as o-(2-PHMBD)-P, o-(2-PHMBD)-H, and o-(2-PHMBD)-O, were successfully obtained and comprehensively characterized by FT-IR, 1H-13C-NMR, UV–Vis, CV, GPC, SEM, TGA, and DSC analyses. Spectroscopic results confirmed the successful polymerization, while morphological and thermal analyses revealed the distinct physical characteristics of the oligomers. According to GPC data, o-(2-PHMBD)-H exhibited the highest average molecular weight of 4700 Da, and TGA analysis demonstrated that o-(2-PHMBD)-O had the highest thermal stability with a residue of 46% at 1000 °C. The DSC results showed the highest glass transition temperature of 132 °C for o-(2-PHMBD)-H. UV–Vis and CV measurements indicated reduced optical and electrochemical band gaps compared with the monomer, with the lowest optical band gap determined as 2.74 eV. Dielectric measurements revealed that o-(2-PHMBD)-H displayed the highest dielectric constant of 2.57 and conductivity of 2.49 × 10⁻7 S cm⁻1. These results demonstrate that phenylhydrazine-based Schiff base oligomers possess high thermal stability and favorable dielectric properties, making them promising materials for optoelectronic and dielectric device applications.

AtıfScopus3·WoS2·OpenAlex4

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