SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST

Ömrüye Özok Arıcı; Şefika Kaya; Aykut Çağlar; Hilal Demir Kıvrak; Arif Kıvrak

doi:10.31796/ogummf.1437602

TR EN

BENZO[B]TİYOFEN BAZLI ORGANİK BİLEŞİKLERİN SENTEZİ VE ANOT KATALİZÖRÜ OLARAK HİDRAZİN ELEKTROOKSİDASYON PERFORMANSI

Öz

Bu çalışmada Sonagashira bağlanma reaksiyonları ve elektrofilik siklizasyon reaksiyonları kullanılarak 3-iodo-2-(p-tolil)benzo[b]tiyofen (4C) sentezlendi. Elektrokimyasal ölçümler, 1 M KOH + 0,5M N2H4 çözeltisi ortamında, döngüsel voltametri (CV), kronoamperometri (CA), elektrokimyasal empedans spektroskopisi (EIS) gibi elektrokimyasal yöntemler kullanılarak gerçekleştirilmiştir. Elde edilen CV sonuçları, 4C katalizörünün en iyi akımın (15.40 mA/cm2) üretimini desteklediğini gösterdi ve EIS sonuçları, aynı türevle modifiye edilen elektrotun en düşük yük transfer direncine sahip olduğunu göstermektedir. Birlikte ele alındığında, bu sonuçlar 4C organik katalizörünün hidrazin (N2H4) yakıt hücrelerinde anot açısından verimli bir katalizör olarak kullanılabileceğini göstermektedir.

Anahtar Kelimeler

Enerji , Yakıt hücresi , Hidrazin , Benzotiyofen , Paladyum

SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST

Abstract

In this study, 3-iodo-2-(p-tolyl)benzo[b]thiophene (4C) is synthesized by using Sonagashira coupling reactions and electrophilic cyclization reactions. Electrochemical measurements have been performed using electrochemical methods such as cyclic voltammetry (CV), chronoamperometry (CA) and electrochemical impedance spectroscopy (EIS) in the environment of 1 M KOH + 0.5M N2H4 solution. The CV results obtained showed that 4C catalyst promoted the generation of the best current (15.40 mA/cm2), and EIS results confirmed that electrode modifeed with the same derivative presented the lowest charge transfer resistance. Taken together, these results suggest that 4C organocatalyst could be used as an anode efficient catalyst in hydrazine (N2H4) fuel cells.

Keywords

Energy , Fuel cell , Hydrazine , Benzothiophene , Palladium

References

Abdullah, S., Kamarudin, S.K., Hasran, U.A., Masdar, M.S. & Daud, W.R.W. (2014). Modeling and simulation of a direct ethanol fuel cell: An overview. Journal of Power Sources, 262, 401-406. doi: https://doi.org/10.1016/j.jpowsour.2014.03.105
Algso, M.A. & Kivrak, A. (2019). New strategy for the synthesis of 3-ethynyl-2-(thiophen-2-yl) benzo [b] thiophene derivatives. Chemical Papers, 73(4), 977-985. doi: https://doi.org/10.1007/s11696-018-0640-2
Caglar, A. & Kivrak, H. (2019). Highly active carbon nanotube supported PdAu alloy catalysts for ethanol electrooxidation in alkaline environment. International Journal of Hydrogen Energy, 44(23), 11734-11743. doi: https://doi.org/10.1016/j.ijhydene.2019.03.118
Cazetta, A.L., Zhang, T., Silva, T.L., Almeida, V.C. & Asefa, T. (2018). Bone char-derived metal-free N-and S-co-doped nanoporous carbon and its efficient electrocatalytic activity for hydrazine oxidation. Applied Catalysis B: Environmental, 225, 30-39. doi: https://doi.org/10.1016/j.apcatb.2017.11.050
Chen, L. X., Jiang, L. Y., Wang, A. J., Chen, Q. Y. & Feng, J. J. (2016). Simple synthesis of bimetallic AuPd dendritic alloyed nanocrystals with enhanced electrocatalytic performance for hydrazine oxidation reaction. Electrochimica Acta, 190, 872-878. doi: https://doi.org/10.1016/j.electacta.2015.12.151
Cho, C.H., Neuenswander, B., Lushington, G.H. & Larock, R.C. (2019). Solution-phase parallel synthesis of a multi-substituted benzo [b] thiophene library. Journal of combinatorial chemistry, 11(5), 900-906. doi: https://doi.org/10.1021/cc9000604
Clarke, T.M. & Durrant, J.R. (2010). Charge photogeneration in organic solar cells. Chemical reviews, 110(11), 6736-6767. doi: https://doi.org/10.1021/cr900271s
Demirbas, A., Sahin-Demirbas, A. & Hilal Demirbas, A. (2004). Global energy sources, energy usage, and future developments. Energy Sources, 26(3), 191-204. doi: https://doi.org/10.1080/00908310490256518
Ding, J., Kannan, P., Wang, P., Ji, S., Wang, H., Liu, Q., Gai, H., Liu, F. & Wang, R. (2019). Synthesis of nitrogen-doped MnO/carbon network as an advanced catalyst for direct hydrazine fuel cells. Journal of Power Sources, 413, 209-215. doi: https://doi.org/10.1016/j.jpowsour.2018.12.050
Er, O.F., Ulas, B., Ozok, O., Kivrak, A. & Kivrak, H., (2021). Design of 2-(4-(2-pentyllbenzo [b] thiophen-3-yl) benzylidene) malononitrile based remarkable organic catalyst towards hydrazine electrooxidation. Journal of Electroanalytical Chemistry, 888, 115218. doi: https://doi.org/10.1016/j.jelechem.2021.115218

Feng, Z., Li, D., Wang, L., Sun, Q., Lu, P., Xing, P. & An, M. (2019). In situ grown nanosheet NiZn alloy on Ni foam for high performance hydrazine electrooxidation. Electrochimica Acta, 304, 275-281. doi: https://doi.org/10.1016/j.electacta.2019.03.017
Guo, S., He, Y., Murtaza, I., Tan, J., Pan, J., Guo, Y., Zhu, Y., He, Y. & Meng, H. (2018). Alkoxy substituted [1] benzothieno [3, 2-b][1] benzothiophene derivative with improved performance in organic thin film transistors. Organic Electronics, 56, 68-75. doi: https://doi.org/10.1016/j.orgel.2018.02.003
Huang, W.T. & Li, Y. (2015). Electrical characteristic fluctuation of 16-nm-gate trapezoidal bulk FinFET devices with fixed top-fin width induced by random discrete dopants. Nanoscale research letters, 10(1), .1-8. doi: https://doi.org/10.1007/s12633-023-02835-3
Keri RS, Chand K, Budagumpi S, Somappa SB, Patil SA, & Nagaraja BM. (2017). An overview of benzo[b]thiophene-based medicinal chemistry. Eur J Med Chem. 138:1002–1033. doi: https://doi.org/10.1016/j.ejmech.2017.07.038
Khoo, K.S., Chia, W.Y., Wang, K., Chang, C.K., Leong, H.Y., Maaris, M.N.B. & Show, P.L. (2021). Development of proton-exchange membrane fuel cell with ionic liquid technology. Science of The Total Environment, 793, 148705. doi: https://doi.org/10.1016/j.scitotenv.2021.148705
Kivrak, H., Can, M., Duru, H. & Sahin, O. (2014). Methanol electrooxidation study on mesoporous silica supported Pt–Co direct methanol fuel cell anode. International Journal of Chemical Reactor Engineering, 12(1), 369-375. doi: https://doi.org/10.1515/ijcre-2014-0051
Morimoto, M., Takagi, Y., Hioki, K., Nagasaka, T., Sotome, H., Ito, S., Miyasaka, H. & Irie, M. (2018). A turn-on mode fluorescent diarylethene: solvatochromism of fluorescence. Dyes and Pigments, 153, 144-149. doi: https://doi.org/10.1016/j.dyepig.2018.02.016
Park, M., Lee, T. & Kim, B.S. (2013). Covalent functionalization based heteroatom doped graphene nanosheet as a metal-free electrocatalyst for oxygen reduction reaction. Nanoscale, 5(24), 12255-12260. doi: https://doi.org/10.1039/C3NR03581F
Peng, M.Y.P., Chen, C., Peng, X. & Marefati, M. (2020). Energy and exergy analysis of a new combined concentrating solar collector, solid oxide fuel cell, and steam turbine CCHP system. Sustainable Energy Technologies and Assessments, 39, 100713. doi: https://doi.org/10.1016/j.seta.2020.100713
Peumans, P., Yakimov, A. & Forrest, S.R. (2003). Small molecular weight organic thin-film photodetectors and solar cells. Journal of Applied Physics, 93(7), 3693-3723. doi: https://doi.org/10.1063/1.1534621
Sahin, O., Duzenli, D. & Kivrak, H. (2016). An ethanol electrooxidation study on carbon-supported Pt-Ru nanoparticles for direct ethanol fuel cells. Energy Sources, Part A: Recovery, Utilization, and Environmental Effects, 38(5), 628-634. doi: https://doi.org/10.1080/15567036.2013.809391
Shi, X., Huo, X., Esan, O.C., An, L. & Zhao, T.S. (2021). Performance characteristics of a liquid e-fuel cell. Applied Energy, 297, 117145. doi: https://doi.org/10.1016/j.apenergy.2021.117145
Ozok, O., Kavak, E., Er, O.F., Kivrak, H. & Kivrak, A. (2020). Novel benzothiophene based catalyst with enhanced activity for glucose electrooxidation. International Journal of Hydrogen Energy, 45(53), 28706-28715. doi: https://doi.org/10.1016/j.ijhydene.2020.07.195
Ulas, B., Caglar, A., Sahin, O. & Kivrak, H. (2018). Composition dependent activity of PdAgNi alloy catalysts for formic acid electrooxidation. Journal of colloid and interface science, 532, 47-57. doi: https://doi.org/10.1016/j.jcis.2018.07.120
Wang, W., Wang, Y., Liu, S., Yahia, M., Dong, Y. & Lei, Z. (2019). Carbon-supported phosphatized CuNi nanoparticle catalysts for hydrazine electrooxidation. International Journal of Hydrogen Energy, 44(21), 10637-10645. doi: https://doi.org/10.1016/j.ijhydene.2019.03.005
Wang, S., Li, W. & Fooladi, H. (2021). Performance evaluation of a polygeneration system based on fuel cell technology and solar photovoltaic and use of waste heat. Sustainable Cities and Society, 72, 103055. doi: https://doi.org/10.1016/j.scs.2021.103055
Wang, Y., Chen, K.S., Mishler, J., Cho, S.C. & Adroher, X.C. (2011). A review of polymer electrolyte membrane fuel cells: Technology, applications, and needs on fundamental research. Applied energy, 88(4), 981-1007. doi: https://doi.org/10.1016/j.apenerg.2010.09.030
Wang, Y., Wan, Y. & Zhang, D. (2010). Reduced graphene sheets modified glassy carbon electrode for electrocatalytic oxidation of hydrazine in alkaline media. Electrochemistry Communications, 12(2), 187-190. doi: https://doi.org/10.1016/j.elecom.2009.11.019
Yang, F. & Forrest, S.R. (2008). Photocurrent generation in nanostructured organic solar cells. ACS nano, 2(5), 1022-1032. doi: https://doi.org/10.1021/nn700447t
Zhao, A., Sun, H., Chen, L., Huang, Y. & Lu, X. (2019). Development of highly efficient and scalable free-standing electrodes for the fabrication of hydrazine-O2 fuel cell. Materials Research Express, 6(8), 085533. doi: https://doi.org/10.1088/2053-1591/ab242f

Details

Primary Language

English

Subjects

Electrochemical Technologies

Journal Section

Research Article

Authors

Ömrüye Özok Arıcı ^*
0000-0002-4164-8650
Türkiye

Şefika Kaya
0000-0001-8277-4365
Türkiye

Aykut Çağlar
0000-0002-0681-1096
Türkiye

Hilal Demir Kıvrak
0000-0001-8001-7854
Türkiye

Arif Kıvrak
0000-0003-4770-2686
Türkiye

Early Pub Date

August 6, 2024

Publication Date

August 12, 2024

Submission Date

February 15, 2024

Acceptance Date

June 14, 2024

Published in Issue

Year 2024 Volume: 32 Number: 2

DOI

https://doi.org/10.31796/ogummf.1437602

IZ

https://izlik.org/JA27NE22CP

APA

Özok Arıcı, Ö., Kaya, Ş., Çağlar, A., Demir Kıvrak, H., & Kıvrak, A. (2024). SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST. Eskişehir Osmangazi Üniversitesi Mühendislik Ve Mimarlık Fakültesi Dergisi, 32(2), 1356-1362. https://doi.org/10.31796/ogummf.1437602

AMA

1.Özok Arıcı Ö, Kaya Ş, Çağlar A, Demir Kıvrak H, Kıvrak A. SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST. Eskişehir Osmangazi Üniversitesi Mühendislik ve Mimarlık Fakültesi Dergisi. 2024;32(2):1356-1362. doi:10.31796/ogummf.1437602

Chicago

Özok Arıcı, Ömrüye, Şefika Kaya, Aykut Çağlar, Hilal Demir Kıvrak, and Arif Kıvrak. 2024. “SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST”. Eskişehir Osmangazi Üniversitesi Mühendislik Ve Mimarlık Fakültesi Dergisi 32 (2): 1356-62. https://doi.org/10.31796/ogummf.1437602.

EndNote

Özok Arıcı Ö, Kaya Ş, Çağlar A, Demir Kıvrak H, Kıvrak A (August 1, 2024) SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST. Eskişehir Osmangazi Üniversitesi Mühendislik ve Mimarlık Fakültesi Dergisi 32 2 1356–1362.

IEEE

[1]Ö. Özok Arıcı, Ş. Kaya, A. Çağlar, H. Demir Kıvrak, and A. Kıvrak, “SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST”, Eskişehir Osmangazi Üniversitesi Mühendislik ve Mimarlık Fakültesi Dergisi, vol. 32, no. 2, pp. 1356–1362, Aug. 2024, doi: 10.31796/ogummf.1437602.

ISNAD

Özok Arıcı, Ömrüye - Kaya, Şefika - Çağlar, Aykut - Demir Kıvrak, Hilal - Kıvrak, Arif. “SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST”. Eskişehir Osmangazi Üniversitesi Mühendislik ve Mimarlık Fakültesi Dergisi 32/2 (August 1, 2024): 1356-1362. https://doi.org/10.31796/ogummf.1437602.

JAMA

1.Özok Arıcı Ö, Kaya Ş, Çağlar A, Demir Kıvrak H, Kıvrak A. SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST. Eskişehir Osmangazi Üniversitesi Mühendislik ve Mimarlık Fakültesi Dergisi. 2024;32:1356–1362.

MLA

Özok Arıcı, Ömrüye, et al. “SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST”. Eskişehir Osmangazi Üniversitesi Mühendislik Ve Mimarlık Fakültesi Dergisi, vol. 32, no. 2, Aug. 2024, pp. 1356-62, doi:10.31796/ogummf.1437602.

Vancouver

1.Ömrüye Özok Arıcı, Şefika Kaya, Aykut Çağlar, Hilal Demir Kıvrak, Arif Kıvrak. SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST. Eskişehir Osmangazi Üniversitesi Mühendislik ve Mimarlık Fakültesi Dergisi. 2024 Aug. 1;32(2):1356-62. doi:10.31796/ogummf.1437602

BENZO[B]TİYOFEN BAZLI ORGANİK BİLEŞİKLERİN SENTEZİ VE ANOT KATALİZÖRÜ OLARAK HİDRAZİN ELEKTROOKSİDASYON PERFORMANSI

Öz

Anahtar Kelimeler

SYNTHESIS OF BENZO[B]THIOPHENE-BASED ORGANIC COMPOUNDS AND THEIR HYDRAZINE ELECTROOXIDATION PERFORMANCE AS AN ANODE CATALYST

Abstract

Keywords

References

Details

Primary Language

Subjects

Journal Section

Authors

Early Pub Date

Publication Date

Submission Date

Acceptance Date

Published in Issue

DOI

IZ

Cite