Synthesis and Properties of Some Polythiophenes Containing Benzo[d]thiazole Heterocycle
Main Article Content
Abstract
In this paper, some new polythiophenes containing benzo[d]thiazole heterocycle were synthesized by the oxidative polymerization in chloroform using iron(III) chloride as a catalytic oxidant. Infrared (IR) spectroscopy and ultraviolet–visible (UV-Vis) spectroscopy analyses confirmed that the polymerization reaction successfully took place and the absorption band at 497 nm is typical for π–π* transition in the conjugated polythiophenes. The polymers are composed of relatively uniform particles using field emission scanning electron microscopy (FESEM) method. Based on thermal gravimetric analysis (TGA), the polymers had average thermal stability in the atmosphere when decomposed completely at 500 oC. The polymers exhibited fluorescence emission at about 516 nm due to the conjugated chain in the polymers.
Keywords:
Polythiophene, benzo[d]thiazole, chemical oxidative polymerization, heterocyclic side groups, electrical conductivity.
References
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[3] Q. T. Vu, N. L. Nguyen, T. T. D. Tran, T. C. Nguyen, K. L. Duong, M. H. Ha, T. Y. O. Doan, Synthesis and Characterization of Novel Poly[4-phenyl-3-(thiophen-3-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione], Vietnam J. Chem., Vol. 57, No. 6, 2019, pp. 770-776.
[4] Q. T. Vu, N. L. Nguyen, T. V. Do, K. L. Duong, M. H. Ha, C. T. Pham, H. H. Nguyen, M. L. Van, Crystal Structure of 4-amino-3-(thiophen-3-yl-methyl)-1H-1,2,4-triazole-5(4H)-thione, Acta Cryst. Section E, Vol. 73, No. 9, 2017, pp. 1389-1392.
[5] Q. T. Vu, N. L. Nguyen, T. C. Nguyen, C. T. Pham, M. L. Van, Crystal Structure of N-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-2-(thiophen-3-yl)acetamide, Acta Cryst, Section E., Vol. 73, No. 6, 2017, pp. 901-904.
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[7] S. Ming, H. Youjun, H. Kunlun, M. R. Christopher, B. G. David, X. A. Kai, Water-Soluble Polythiophene for Organic Field-Effect Transistors, Polymer Chemistry, Vol. 4, No. 20, 2013, pp. 5270-5274.
[8] J. Pei, W. L. Yu, J. Ni, Y. H. Lai, W. Huang, A. J. Heeger, Thiophene-based Conjugated Polymers for Light-Emitting Diodes: Effect of Aryl Groups on Photoluminescence Efficiency and Redox Behavior, Macromolecule, Vol. 34, No. 21, 2001, pp. 7241.
[9] G. A. Snook, P. Kao, A. S. Best, Conducting-Polymer-based Supercapacitor Devices and Electrodes, J. Power Sources, Vol. 196, No. 1, 2011, pp. 1-12.
[10] T. Ghaitaoui, B. Ali, Y. Hamid, K. Sahli, Realization and Characterization of p-Typed Polythiophene based Organic Photovoltaic Cells, Journal of Nano- and Electronic Physics, Vol. 10, No. 1, 2018, pp. 01008.
[11] M. Nabasmita, G. Radhakanta, K. A. Nandi, Optoelectronic Properties of Self-assembled Nanostructures of Polymer Functionalized Polythiophene and Graphene, Langmuir., Vol. 34, No. 26, 2018, pp. 7585-7597.
[12] D. C. Borrelli, S. Lee, K. K. Gleason, Optoelectronic Properties of Polythiophene Thin Films and Organic TFTs Fabricated by Oxidative Chemical Vapor Deposition, Journal of Material Chemistry C., Vol. 35, No. 2, 2014, pp. 7223-7231.
[13] S. Aiello, G. Wells, E. L. Stone, H. Kadri, R. Bazzi, D. R. Bell, M. F. Stevens, C. S. Matthews, T. D. Bradshaw, A. D. Westwell, Synthesis and Biological Properties of Benzothiazole, Benzoxazole, and Chromen-4-one Analogues of the Potent Antitumor Agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648), J. Med. Chem., Vol. 51, No. 16, 2008, pp. 5135-5139.
[14] Y. Cho, T. R. Ioerger, J. C. Sacchettini, Discovery of Novel Nitrobenzothiazole Inhibitors for Mycobacterium Tuberculosis ATP Phosphoribosyl Transferase (HisG) through Virtual Screening, J. Med. Chem., Vol. 51, No. 19, 2008, pp. 5984-5992.
[15] N. L. Nguyen, M. H. Ha, T. Y. O. Doan, T. T. L. Bui, T. C. Nguyen, T. C. Nguyen, H. Thai, Q. T. Vu, Fluorescent Properties of Some Polythiophenes Synthesized from 2-(thiophen-3-yl)acetohydrazide and Acetophenone, Vietnam J. Chem, Vol. 58, No. 5, 2020, pp. 689-697.
[16] S. Radhakrishnan, R. Parthasarathi, V. Subramanian, N. Somanathan, Structure and Properties of Polythiophene Containing Hetero Aromatic Side Chains, J. Comput. Mater. Sci., Vol. 37, 2006, pp. 318-322.
[17] K. Esashika, M. Yoshizawa-Fujita, Y. Takeoka, M. Rikukawa, Synthesis and Optical Properties of Poly(thiophene-fluorene) Copolymers with Benzothiazole Moiety, Synth. Met., Vol. 159, 2009, pp. 2184-2187.
[18] S. Radhakrishnan, V. Subramanian,
N. Somanathan, K. S. V. Srinivasan, T. Ramasami, Synthesis, Structure and Band Gap of Novel Thiophene Based Conductive Polymers, Mol. Cryst. Liq. Cryst., Vol. 390, 2003, pp. 113-120.
[19] N. L. Nguyen, Q. T. Vu, Q. H. Duong, Q. M. Vu, M. L. Truong, C. T. Pham, Me. L. Van, Green Synthesis and Crystal Structure of 3-(benzothiazol-2-yl)thiophene, Acta Cryst. E, Vol. E73, 2017, pp. 1647-1651.
[20] B. Y. Lu, J. Yan, J. K. Xu, S. Y. Zhou, X. J. Hu, Novel Electroactive Proton-doped Conducting Poly(aromatic ethers) with Good Fluorescence Properties via Electropolymerization, Macromolecules, Vol. 43, No. 10, 2010,
pp. 4599-4608.
[21] K. Lin, S. Zhang, H. Liu, Y. Zhao, Z. Wang, J. Xu, Effects on the Electrochemical and Electrochromic Properties of 3 Linked Polythiophene Derivative by the Introduction of Polyacrylate, Int. J. Electrochem. Sci., Vol. 10, 2015, pp. 7720-7731.
[22] B. X. Valderrama-García, E. Rodríguez-Alba, E. G. Morales-Espinoza, K. M. Chane-Ching,
R. Ernesto, Synthesis and Characterization of Novel Polythiophenes Containing Pyrene Chromophores: Thermal, Optical and Electrochemical Properties, Molecules, Vol. 21, 2016, pp. 172-189.
[23] Q. T. Vu, N. L. Nguyen, T. C. Nguyen, C. T. Pham, M. L. Van, Crystal Structure of N-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)-2-(thiophen-3-yl)acetamide, Acta Crystallographica Section E, Vol. E73, 2017, pp. 901-904.
[24] G. Dipanjan, S. N. Islam, K. P. Sanjib, Synthesis and Characterization of 1,2,3-Triazole Appended Polythiophene Based Reusable Fuorescent Probe for the Efficient Detection of Trace Nitroaromatics, Polymer, Vol. 134, 2018, pp. 242-253.
[25] T. Yamamoto, D. Komarudin, M. Arai, B. L. Lee, H. Suganuma, N. Asakawa, Y. Inoue, K. Kubota, Sh. Sasaki, T. Fukuda, H. Matsuda, Extensive Studies on π-Stacking of Poly(3-alkylthiophene-2,5-diyl)s and Poly(4-alkylthiazole-2,5-diyl)s by Optical Spectroscopy, NMR Analysis, Light Scattering Analysis and Xray Crystallography, J. Am. Chem. Soc., Vol. 120, No. 9, 1998, pp. 2047-2058.