THE STUDY OF 2,4-DINITROPHENYL HYDRAZINE DERIVATIVE COMPOUNDS SYNTHESIS AS OLED COMPOUND PRECURSORS

• Main Author: FELIX MEIDIANTO (NIM : 105 08 082); ; Pembimbing I : Dr. Deana Wahyuningrum; Pembimbing , VINCENCIUS
• Format: Final Project
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/17507
• Institution: Institut Teknologi Bandung

Luminesence is a phenomenon that comes up from certain substances. It has been used in many applications. One of its applications is in OLED (Organic Light Emitting Diode) based devices. A compound used in OLED based device is generally a rigid conjugated organic molecule or complex compund with transition metal ion such as Cu, Pt, Ir. In this reseach, two hydrazone compounds have been successfully synthesized using DNPH (2,4-dinitrophenyl hydrazine) as the precursor. First, Hydrazone A compound, 1-(2,4-dinitrophenyl)-2-(propan-2-ylidene) hydrazine, is yellowish solid with melting point of 120 –122oC. It was synthesized by the reflux method with 98.92% of chemical yields. Second, Hydrazone B compound, 1-(2,4-dinitrophenyl)-2-(diphenylmethylene)hydrazine, which is <br /> <br /> <br /> <br /> <br /> <br /> <br /> more conjugated than Hydrazone A, was synthesized by MAOS (Microwave Assisted Organic Synthesis) method using two different catalysts, which are HCl and SSA (Silica <br /> <br /> <br /> <br /> <br /> <br /> <br /> Sulfuric Acid), with chemical yields are 65.38% and 39.10%, respectively. Hydrazone B is orange solid which decomposed at 220oC. Infared spectoscopy data result shows <br /> <br /> <br /> <br /> <br /> <br /> <br /> characteristic vibrational peaks of imine (C=N) for Hydrazone A and Hydrazone B at 1619.85 cm-1 and 1617.02 cm-1, respectively. The structure confirmation of Hydrazone A <br /> <br /> <br /> <br /> <br /> <br /> <br /> and Hydrazone B was determined using 1H-NMR and 13C NMR. Mass spectroscopy (ESIMS) measurement of Hydrazone A shows m/z peak of 239.0787 (ESI+). The 13C NMR spectrum of Hydrazone A shows nine carbon signals. One of the signals represents imine carbon at 155.51 ppm. The 13C NMR spectrum of Hydrazone B shows fifteen signals which correlates to eighteen aromatic carbons and one imine carbon at 155.82 ppm. Emmision wavelength of fluorescence spectrophotometry measurements for Hydrazone A and Hydrazone B are 654 and 524 nm, respectively. Maximum wavelength of UV-Vis <br /> <br /> <br /> <br /> <br /> <br /> <br /> spectrophotometry measurements for Hydazone A and Hydrazone B are 375 and 394 nm, respectively. Based on all of the analyzed data, it can be concluded that Hydrazone A and <br /> <br /> <br /> <br /> <br /> <br /> <br /> Hydrazone B have the potent as OLED compound precursors. In this research, synthesis of Cu2+ complex with DNPH and Zn2+ complex compound with Hydrazone A have been perfomed by sonochemistry and reflux method, respectively. Unfortunately, the complexes were not formed yet.