Theoretical and Spectroscopic Studies of N-([4-aminophenyl]ethynyltoluene)-N’-(1-naphthanoyl thiourea (ATT) as Carbon Monoxide Gas Chemosensor

Abstract:

Acetylide and thiourea moieties individually provides a wide range of electronic properties as they possess electronic delocalization in extended rigid π orbital system in their designated structures. In this work, a new derivative of N-([4–aminophenyl] ethynyltoluene)-N’-(1-naphthanoyl) thiourea (ATT) was successfully synthesized and spectroscopically characterized by using FT-IR, NMR, and UV-Vis analysis. In turn, the development of new sensing material thin-film based on ATT has been accomplished by incorporating with polyvinyl chloride (PVC) via dip-coating technique. The difference in absorption behavior using UV-visible spectroscopic analysis was employed to determine the sensitivity of thin-film towards carbon monoxide (CO) gas of 10, 20, and 30 ppm. ATT exhibits high sensitivity towards 30 ppm CO gas with 55% sensitivity. Quantum mechanical calculation via Gaussian 09 shows that ATT has potential van der Waals interaction towards CO with stabilization energy-6.54 kJ/mol and 3.14Ǻ of interaction distance between substrate and analyte. It is proven that ATT as single molecule gives great potential to be explored and used as sensing material application particularly in CO detection.

• Periodical: Applied Mechanics and Materials (Volumes 719-720)
• Pages: 59-62
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.719-720.59
• Online since: January 2015
• Authors: Wan Mohd Khairul, Adibah Izzati Daud, Hafiza Mohamed Zuki, K. Kubulat
• Keywords: Acetylide, CO Gas Sensor, Single Molecule, Thiourea

References

[1] J. A. Raub, M. Marthieu-Nolf, N. B. Hampson, S. R. Thom, Carbon monoxide poisoning—a public health perspective, Toxicology. 145 (2000) 1-14.

DOI: 10.1016/s0300-483x(99)00217-6

[2] P. G. Flachsbart, Human exposure to carbon monoxide from mobile sources, Chemosphere: Global Change Science. 1 (1999) 301-329.

DOI: 10.1016/s1465-9972(99)00030-6

[3] G. Li, H. Lin, H. Wang, F. Wang, A novel nanometer-scale 'gold electrode-molecular wires-silver', junction: An efficient test bed for electrochemical investigation of electron transportation through molecular wires in self-assembled monolayers, Electrochem Commun. 8 (2006).

DOI: 10.1016/j.elecom.2005.10.017

[4] H. Bai, G. Shi, Gas sensors based on conducting polymers, Sensors. 7 (2007) 267-307.

DOI: 10.3390/s7030267

[5] E. Sayah, D. Brouri, Y. Wu, A. Musi, P. Da Costa, P. Massiani, A TEM and UV–visible study of silver reduction by ethanol in Ag–alumina catalysts, Applied Catalysis A: General. 406 (2011) 94-101.

DOI: 10.1016/j.apcata.2011.08.016

[6] V. E. Kurochkin, E. D. Makarova, Reflectance spectrophotometry of plasticized membranes for the design of fast optical chemosensors, Anal Commun. 33 (1996) 115-116.

DOI: 10.1039/ac9963300115

[7] Z. Zhong, R. Xing, S. Liu, L. Wang, S. Cai, P. Li, Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro, Carbohyd Res. 343 (2008) 566-570.

DOI: 10.1016/j.carres.2007.11.024

[8] N. B. Arslan, C. Kazak, F. Aydın, N-(4-Nitrobenzoyl)-N-(1, 5-dimethyl-3-oxo-2-phenyl-1 H-3 (2H)-pyrazolyl)-thiourea hydrate: Synthesis, spectroscopic characterization, X-ray structure and DFT studies, Spectrochim Acta A. 89 (2012) 30-38.

DOI: 10.1016/j.saa.2011.12.040

[9] A. Kausar, S. Zulfiqar, Z. Ahmad, M. I. Sarwar, Studies on novel thermally stable segmented polyurethanes based on thiourea-derivative diols, Polym Degrad Stabil. 95(12), (2010) 2281-2288.

DOI: 10.1016/j.polymdegradstab.2010.09.006

[10] S. Saeed, N. Rashid, P. G. Jones, M. Ali, R. Hussain, Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents , Eur. J. Med. Chem. 45 (2010).

DOI: 10.1016/j.ejmech.2009.12.016

[11] Y. F. Yuan, J. T. Wang, M. C. Gimeno, A. Laguna, P. G. Jones, Synthesis and characterisation of copper complexes with N-ferrocenoyl- N'-aryl (alkyl) thioureas, Inorg. Chim. Acta. 324 (2001) 309-317.

DOI: 10.1016/s0020-1693(01)00661-2

[12] W. M. Khairul, M. F. Yusof, R. Rahamathullah, A. I. Daud, S. M. Jasman, M. F. A. Hasan, M. G. Tay, Single Molecule Thin Film Featuring Disubstituted Thiourea (TU) Doped with Chlorophyll as Potential Active Layer in Photovoltaic Cell, Int. J. Electrochem. Sci. 8 (2013).

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

[13] G. L. Miessler, D. A. Tarr, Inorganic Chemistry. Pearson Education. Upper Saddle River, NJ, 345. (2004).

[14] F. Tavoli, N. Alizadeh, Optical ammonia gas sensor based on nanostructure dye-doped polypyrrole Sensor. Actuat. B-Chem. 176 (2013) 761-767.

DOI: 10.1016/j.snb.2012.09.013