Study on the Transformation Reaction of N,N-diphenylamine to 4-Nitrodiphenylamine in the Presence of Ionic Liquid (1-Methyl-3-Sulfonic Acid Imidazolium Chloride) as Organic Light Emitting Diode (OLED) Precursor Material

• Main Author: Anhar, Faizul
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/32269
• Institution: Institut Teknologi Bandung

Organic Light Emitting Diode (OLED) is one of the high-end technology materials developed utilizing organic compounds, especially aromatic compounds which have conjugated double bonds. This topic is becoming more interesting because the utilizing of organic compounds for emissive layer of OLED has some advantages compared to inorganic compounds. Therefore, one of the aims of this research is to study on the transformation of N,N-diphenylamine to become 4-nitrodiphenylamine that has the potential to be used as a material OLED precursor using the ionic liquid 1-methyl-3-sulfonate imidazolium chloride ([Msim]Cl) as a solvent. In this research, the transformation of N,N-diphenylamine was carried out through the nitration reaction using 1-methyl-3-sulfonic imidazolium chloride as medium or solvent. Initially, the ionic liquid 1-methyl-3-sulfonic imidazolium chloride was synthesized and its structure was confirmed using FTIR and NMR. FTIR spectra of [Msim]Cl (KBr pellet) showed characteristic peaks at wavenumbers of 1080,14 cm-1, 1109,07 cm-1, and 1284,59 cm-1 that correspond to the typical absorption of functional group S=O, N-SO2, and O-SO2, respectively. 1H-NMR spectra of [Msim]Cl (500 MHz, CDCl3) shows 4 proton signals at chemical shifts of 3,99 (s, 3H, CH3); 7,55 (s, 1H); 7,60 (s, 1H); 8,91 (s, 1H); and 12,50 (s, 1H) ppm. Furthermore, the transformation of N,N-diphenylamine was performed using [Msim]Cl as solvent with some variations in reaction time (3-11 minutes). The optimal reaction condition was achieved at the reaction time for 9 minutes and the yields of product obtained is 77,36%. The product of the nitration reaction was further characterized using IR, 1H-NMR, UV-Vis and fluorescence spectroscopies. The FT-IR spectrum of product (KBr pellet) showed peaks at wavenumbers of 1251,80 cm-1 which is the characteristic absorption of nitro functional groups. The 1H-NMR spectrum (500MHz, CDCl3) of product showed 4 proton signals at chemical shift of 6,42 (s, 1H); 6,91 (d, 2H); 7,06 – 7,50 (m, 3H); and 7,80 (d, 1H) ppm which is typical proton chemical shifts of 4-nitrodiphenylamine. The maximum wavelengths of UV-Vis absorption spectrum of 4-nitrodiphenylamine in acetone was found to be 329 and 395 nm. 4-Nitrodiphenylamine emits light at wavelengths of 398 nm, 420 nm, and 699 nm. Based on the results it can be concluded that 4-nitrodiphenylamine has the potential to be used as OLED material precursor as it can emit the light in the visible light region.