Naphthoyl-Thiourea Thin Film as Potential OLED Featuring Methyl Pyridine Moiety

Abstract:

Thiourea derivatives have attracted great attention as potential materials to be used in molecular electronics application due to their fairly rigid p-system properties. Thus, in this study N-((6-metylpyridin-3-yl)carbamothioyl)-1-naphtamide (NT) has been successfully designed, synthesized and characterized by typical spectroscopic techniques namely Infrared Spectroscopy (IR), ¹H and ¹³C Nuclear Magnetic Resonance (NMR), UV-Vis, Four Point Probe to measure its conductivity and finally ab initio quantum mechanical evaluation at the theoretical level of DFT B3LYP/6-31G (d,p). In turn, NT was coated on the ITO substrate by using electrochemical deposition method. The electrical conductivity of this compound as a thin film exhibited good and ideal result which was 1.7x10^-4Scm^-1. Owing to this outstanding result, this single molecular system candidate has wide possibilities to be applied in many molecular rectification applications such as Organic Light Emitting diodes (OLED). Further investigation can be carried out by conducting and analyse the I-V curve to measure the efficiency of this compound and other similar molecular frameworks in the near future.

• Periodical: Advanced Materials Research (Volume 1107)
• Pages: 672-677
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.1107.672
• Online since: June 2015
• Authors: Wan Mohd Khairul*, Siti Maryam Jasman, Tei Tagg, K. Kubulat
• Keywords: Gaussian, Napthoyl-Thiourea Derivatives, Organic Light Emitting Diode (OLED)

References

[1] T. H. Kim, W. Wang. & Q. Li. Advancement in materials for energy-saving lighting devices. Front. Chemical Engineering Science. 6(1) (2012) 13-26.

[2] B-T. Chen, Y-H. Tai, Y-J. Kuo, C-C. Tsai. & H-C. Cheng. New pixel circuits for driving active matrix organic light emitting diodes. Solid-State Electronics 50(2) (2006) 272–275.

DOI: 10.1016/j.sse.2005.12.016

[3] C. Alkan, Y. Tek. & D. Kahraman. Preparation and characterization of a series of thiourea derivatives as phase change materials for thermal energy storage. Turkish Journal of Chemistry. 35(5) (2011) 769-777.

DOI: 10.3906/kim-1008-3

[4] H. K. Adli, W. M. Khairul and H. Salleh. Synthesis, Characterization and Electrochemical Properties of Single Layer Thin Film of N-Octaxyphenyl-N'-(4-Chlorobenzoyl)Thiourea-Chlorophyll as Potential Organic Photovoltaic Cells. International Journal of Electrochemical Science. 7 (2012).

DOI: 10.1016/s1452-3981(23)13354-2

[5] R. Rahamathullah, W. M. Khairul, H. Salleh, H. K. Adli, M. I. N. Isa and M. G. Tay. Synthesis, Characterization and Electrochemical Analysis of V-Shaped Disubstituted Thiourea-Chlorophyll Thin Film as Active Layer in Organic Solar Cells. International Journal of Electrochemical Science. 8 (2013).

DOI: 10.1016/s1452-3981(23)14394-x

[6] W. M. Khairul, M. F. Yusof, R. Rahamathullah, A. I. Daud, S. M. Jasman, M. F. A. Hasan, H. Salleh, H. K. Adli and M. G. Tay. Single Molecule Thin Film Featuring Disubstituted Thiourea (TU) Doped with Chlorophyll as Potential Active Layer in Photovoltaic Cell. International Journal of Electrochemical Science. 8 (2013).

DOI: 10.1016/s1452-3981(23)12877-x

[7] R. H. Jusoh, W. M. Khairul, M. S. M. Yusof, M. A. Kadir and B. M. Yamin. Structural and spectroscopic studies of novel methylbenzoylthiourea derivatives. The Malaysian Journal of Analytical Sciences. 1(15) (2011) 70-80.

[8] C. M. Ozer, H. Arslam, D. VanDerveer. & N. Kulcu. Synthesis and characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide Derivatives: The Crystal Structure of N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamid. Molecules 14(2) (2009).

DOI: 10.3390/molecules14020655

[9] S. R. Ghazali, W. M. Khairul. & M. Shamsuddin. Synthesis and Characterisation of Palladium (II) Complex of (N-Pentanoylthioreido)-N'-Propanoic Acid and Its Application as Catalyst in Heck Cross Coupling Reaction. Australian Journal of Basic and Applied Sciences. 7(9) (2013).

[10] J. Pathak, V. Narayan, L. Sinha. & O. Prasad. Theoretical Raman and FTIR vibrational analysis of 2-phenyl-1H-indene-1, 3(2H)-dione by ab initio method. Journal of Atomic and Molecular Sciences 3 (2012) 95-105.

DOI: 10.4208/jams.051111.063011a

[11] O. Estevez-Hernandez, E. Otazo-Sanchez, J. L. Hidalgo-Hidalgo de Cisneros, E. Reguera. A Raman and infrared study of 1-furoyl-3-monosubstituted and 3, 3-disubstituted thioureas. Spectrochimica Acta Part A. 62(4-5) (2005) 964-971.

DOI: 10.1016/j.saa.2005.04.016

[12] S. M. Jasman, W. M. Khairul. & M. Shamsudin. Spectroscopic and Thermal Studies of Palladium (II) Complex of N-(5-methylpyridin-2-ylcarbamothiol) Cinnamamide Ligand. Research Journal of Recent Sciences. 2(11) (2013) 12-19.

[13] D. L. Pavia, G. M. Lampman. & G. S. Kriz. 2001. Introduction to Spectroscopy. 3rd edition. Thomson Learning Inc.

[14] J. Liu, S. Yang, X. Li, H. Fan, P. Bhadury, W. Xu, J. Wu. & Z. Wang. Synthesis and Antiviral Bioactivity of Chiral Thioureas Containing Leucine and Phosphonate Moieties. Molecules. 15(8) (2010) 5112-5123.

DOI: 10.3390/molecules15085112

[15] G. Kavak, S. Ozbey, G. Binzet. & N. Kulcu. Synthesis and single crystal structure analysis of tree novel benzoylthiourea derivatives. Turkish Journal of Chemistry. 33 (2009) 857-868.

DOI: 10.3906/kim-0901-1

[16] S. Rajeswari, G. V. Prabhu. & V. Ramkumar. Spectroscopic Studies and Crystal Structure of 1-[(2, 5-dioxopyrrolidin-1- yl)(phenyl) methyl] Thiourea. Journal of Chemical Crystallography. 39(9) 2009 650-654.

DOI: 10.1007/s10870-009-9538-8

[17] C. Reichaedt. Solvatochromic Dyes as Solvent Polarity Indicators. Chemical Reviews. 94 (1994) 2319-2358.

DOI: 10.1021/cr00032a005

[18] M. H. Harun, E. Sainon, A. Kassim, N. Yahya. & E. Mahmud. Conjugated Conducting Polymers: A Brief Overview. JASA 2. (2007) 63-68.