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Title: Microwave assisted transformation of N,N-diphenylamine as precursors of organic light emitting diodes (OLED)

Abstract

In this research, study on the transformation of N,N-diphenylamine (DPA) using iodine (I2) utilizing solid state Microwave Assisted Organic Synthesis (MAOS) method has been carried out. The reaction was performed by variations of three parameters namely the mole of reagents, the amount and type of solid support (alumina/Al2O3), and the reaction conditions. Experimental results showed that neutral-alumina was a better solid support than basic-alumina. The optimum temperature for the reaction was approximately at 125-133 °C with reaction time of 15 minutes and microwave reactor power at 500-600 W. The separation of the yellowish green product solution with preparative Thin Layer Chromatography (TLC) method using n-hexane:ethyl acetate = 4:1 (v/v) as eluent yielded two fractions (I and II) and both fractions can undergo fluorescence under 365 nm UV light. Based on the LC chromatogram with methanol:water = 95:5 (v/v) as eluent and its corresponding mass spectra (ESI+), fraction I contained three compounds, which were tetracarbazole A, triphenylamine, and impurities in the form of plasticizer such as bis(2-ethylhexyl) phthalate. Fraction II also contained three compounds, which were tetracarbazole C, tetraphenylhydrazine, and plasticizer such as bis(2-ethylhexyl) phthalate. Both FT-IR (KBr disks) and NMR (500 MHz, CDCl{sub 3}) spectra of fraction I and II confirmed the aromaticmore » amine groups in those compounds. The observed fluorescence colors of fraction I and II were violet and violet-blue, respectively. Based on their structures and fluorescence characters, the compounds in fraction I and II have the potential to be used as Organic Light Emitting Diode (OLED) compound precursors.« less

Authors:
;  [1]
  1. Organic Chemistry Research Division, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Jalan Ganesha 10, Bandung 40132 (Indonesia)
Publication Date:
OSTI Identifier:
22488931
Resource Type:
Journal Article
Resource Relation:
Journal Name: AIP Conference Proceedings; Journal Volume: 1677; Journal Issue: 1; Conference: 5. international conference on mathematics and natural sciences, Bandung (Indonesia), 2-3 Nov 2014; Other Information: (c) 2015 AIP Publishing LLC; Country of input: International Atomic Energy Agency (IAEA)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ACETATES; ALUMINIUM OXIDES; AMINES; ATOMIC DISPLACEMENTS; FLUORESCENCE; FOURIER TRANSFORMATION; HEXANE; INFRARED SPECTRA; IODINE; LIGHT EMITTING DIODES; MASS SPECTRA; METHANOL; MHZ RANGE; MICROWAVE RADIATION; PLASTICIZERS; POTASSIUM BROMIDES; REAGENTS; SYNTHESIS; THIN-LAYER CHROMATOGRAPHY; ULTRAVIOLET RADIATION

Citation Formats

Jefri,, and Wahyuningrum, Deana, E-mail: deana@chem.itb.ac.id. Microwave assisted transformation of N,N-diphenylamine as precursors of organic light emitting diodes (OLED). United States: N. p., 2015. Web. doi:10.1063/1.4930716.
Jefri,, & Wahyuningrum, Deana, E-mail: deana@chem.itb.ac.id. Microwave assisted transformation of N,N-diphenylamine as precursors of organic light emitting diodes (OLED). United States. doi:10.1063/1.4930716.
Jefri,, and Wahyuningrum, Deana, E-mail: deana@chem.itb.ac.id. Wed . "Microwave assisted transformation of N,N-diphenylamine as precursors of organic light emitting diodes (OLED)". United States. doi:10.1063/1.4930716.
@article{osti_22488931,
title = {Microwave assisted transformation of N,N-diphenylamine as precursors of organic light emitting diodes (OLED)},
author = {Jefri, and Wahyuningrum, Deana, E-mail: deana@chem.itb.ac.id},
abstractNote = {In this research, study on the transformation of N,N-diphenylamine (DPA) using iodine (I2) utilizing solid state Microwave Assisted Organic Synthesis (MAOS) method has been carried out. The reaction was performed by variations of three parameters namely the mole of reagents, the amount and type of solid support (alumina/Al2O3), and the reaction conditions. Experimental results showed that neutral-alumina was a better solid support than basic-alumina. The optimum temperature for the reaction was approximately at 125-133 °C with reaction time of 15 minutes and microwave reactor power at 500-600 W. The separation of the yellowish green product solution with preparative Thin Layer Chromatography (TLC) method using n-hexane:ethyl acetate = 4:1 (v/v) as eluent yielded two fractions (I and II) and both fractions can undergo fluorescence under 365 nm UV light. Based on the LC chromatogram with methanol:water = 95:5 (v/v) as eluent and its corresponding mass spectra (ESI+), fraction I contained three compounds, which were tetracarbazole A, triphenylamine, and impurities in the form of plasticizer such as bis(2-ethylhexyl) phthalate. Fraction II also contained three compounds, which were tetracarbazole C, tetraphenylhydrazine, and plasticizer such as bis(2-ethylhexyl) phthalate. Both FT-IR (KBr disks) and NMR (500 MHz, CDCl{sub 3}) spectra of fraction I and II confirmed the aromatic amine groups in those compounds. The observed fluorescence colors of fraction I and II were violet and violet-blue, respectively. Based on their structures and fluorescence characters, the compounds in fraction I and II have the potential to be used as Organic Light Emitting Diode (OLED) compound precursors.},
doi = {10.1063/1.4930716},
journal = {AIP Conference Proceedings},
number = 1,
volume = 1677,
place = {United States},
year = {Wed Sep 30 00:00:00 EDT 2015},
month = {Wed Sep 30 00:00:00 EDT 2015}
}
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