Copyright (c) 2025 Meena Lande

This work is licensed under a Creative Commons Attribution 4.0 International License.
Iron Oxide Nanoparticles as an Efficient Catalyst for Azide-Alkyne Cycloaddition Reaction
Corresponding Author(s) : Anjali S. Rajbhoj
Asian Journal of Chemistry,
Vol. 37 No. 7 (2025): Vol 37 Issue 7, 2025
Abstract
The current work focused on the synthesis of iron oxide nanoparticles by electrochemical method and its application in sustainable and eco-friendly copper-free method for the azide–alkyne cycloaddition reactions using a mild-conditions. The electrochemical reduction method was used to synthesize the iron oxide nanoparticles (IONPs) by optimizing the current density of 10 mA/cm2 and tetrapropylammonium bromide as a structure-directing agent in an organic medium. A conventional electrolysis cell was used to generate nanoparticles, with a readily available iron metal sheet acts as an anode and a platinum sheet served as a cathode. The synthesized iron oxide nanoparticles were characterized using FTIR, XRD, SEM and energy dispersive X-ray analysis techniques. The reaction is regioselective as Huisgen 1,3-dipolar cycloaddition reaction where 1,4-disubstituted 1,2,3-triazole formed as product. IONPs could be magnetically collected and also reused without any significant loss of its catalytic activity. The synthesized 1,2,3-triazole products were characterized by FTIR, 1H NMR and 13C NMR.
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- J. Tucek, L. Machala, S. Ono, A. Namai, M. Yoshikiyo, K. Imoto, H. Tokoro, S.-i. Ohkoshi and R. Zboril, Sci. Rep., 5, 15091 (2015); https://doi.org/10.1038/srep15091
- X. Su, S. Chen and Z. Zhou, Appl. Surf. Sci., 258, 5712 (2012); https://doi.org/10.1016/j.apsusc.2012.02.067
- K. Wongwailikhit and S. Horwongsakul, Mater. Lett., 65, 2820 (2011); https://doi.org/10.1016/j.matlet.2011.05.063
- A. Lassenberger, T.A. Grünewald, P.D.J. van Oostrum, H. Rennhofer, H. Amenitsch, R. Zirbs, H.C. Lichtenegger and E. Reimhult, Chem. Mater., 29, 4511 (2017); https://doi.org/10.1021/acs.chemmater.7b01207
- P. A. Calderón Bedoya, P. M. Botta, P. G. Bercoff, and M. A. Fanovich, J. Alloys Compd., 860, 157892 (2021); https://doi.org/10.1016/j.jallcom.2020.157892
- P. Bhavani, C.H. Rajababu, M.D. Arif, I.V.S. Reddy and N.R. Reddy, J. Magn. Magn. Mater., 426, 459 (2017); https://doi.org/10.1016/j.jmmm.2016.09.049
- A. Criveanu, F. Dumitrache, C. Fleaca, L. Gavrila-Florescu, I. Lungu, I.P. Morjan, V. Socoliuc and G. Prodan, Appl. Surf. Sci. Adv., 15, 100405 (2023); https://doi.org/10.1016/j.apsadv.2023.100405
- G. Salazar-Alvarez, M. Muhammed and A.A. Zagorodni, Chem. Eng. Sci., 61, 4625 (2006); https://doi.org/10.1016/j.ces.2006.02.032
- R. Tischendorf, M. Simmler, C. Weinberger, M. Bieber, M. Reddemann, F. Fröde, J. Lindner, H. Pitsch, R. Kneer, M. Tiemann, H. Nirschl and H.-J. Schmid, J. Aerosol Sci., 154, 105722 (2021); https://doi.org/10.1016/j.jaerosci.2020.105722
- M.O. Besenhard, A.P. LaGrow, A. Hodzic, M. Kriechbaum, G. Bais, L. Panariello, K. Loizou, S. Damilos, M. Margarida Cruz, N.T.K. Thanh and A. Gavriilidis, Chem. Eng. J., 399, 125740 (2020); https://doi.org/10.1016/j.cej.2020.125740
- R. Arbain, M. Othman and S. Palaniandy, Miner. Eng., 24, 1 (2011); https://doi.org/10.1016/j.mineng.2010.08.025
- O.I. Kuntyi, A.R. Kytsya, I.P. Mertsalo, A.S. Mazur, G.I. Zozula, L.I. Bazylyak and R.V. Topchak, Colloid Polym. Sci., 297, 689 (2019); https://doi.org/10.1007/s00396-019-04488-4
- R.A. Khaydarov, R.R. Khaydarov, O. Gapurova, Y. Estrin and T. Scheper, J. Nanopart. Res., 11, 1193 (2009); https://doi.org/10.1007/s11051-008-9513-x
- A. Rani, G. Singh, A. Singh, U. Maqbool, G. Kaur and J. Singh, RSC Adv., 10, 5610 (2020); https://doi.org/10.1039/C9RA09510A
- M.S. Jangale, N.D. Bhoge, G.M. Sonwane, A.A. Pund and B.K. Magare, J. Mol. Struct., 1308, 138033 (2024); https://doi.org/10.1016/j.molstruc.2024.138033
- M.M. Mudgal, N. Birudukota and M.A. Doke, Int. J. Med. Chem., 2018, 2946730 (2018); https://doi.org/10.1155/2018/2946730
- L.L. Brockunier, M.R. Candelore, M.A. Cascieri, Y. Liu, L. Tota, M.J. Wyvratt, M.H. Fisher, A.E. Weber and E.R. Parmee, Bioorg. Med. Chem. Lett., 11, 379 (2001); https://doi.org/10.1016/S0960-894X(00)00669-7
- K. Bozorov, J. Zhao and H. A. Aisa, Bioorg. Med. Chem., 27, 3511 (2020); https://doi.org/10.1016/j.bmc.2019.07.005
- R. Huisgen, Angew. Chem., 13, 604 (1963); https://doi.org/10.1002/ange.19630751304
- M. Gauthier and G. Whitton, Polymers, 9, 540 (2017); https://doi.org/10.3390/polym9100540
- V.V. Rostovtsev, L.G. Green, V.V. Fokin and K.B. Sharpless, Angew. Chem., 114, 2708 (2002); https://doi.org/10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0
- F. Alonso, Y. Moglie and G. Radivoy, Acc. Chem. Res., 48, 2516 (2015); https://doi.org/10.1021/acs.accounts.5b00293
- M. Chetia, A.A. Ali, D. Bhuyan, L. Saikia and D. Sarma, New J. Chem., 39, 5902 (2015); https://doi.org/10.1039/C5NJ00754B
- G. Molteni, A.M. Ferretti, M.I. Trioni, F. Cargnoni and A. Ponti, New J. Chem., 43, 18049 (2019); https://doi.org/10.1039/C9NJ04690A
- M.T. Reetz and W. Helbig, J. Am. Chem. Soc., 116, 7401 (1994); https://doi.org/10.1021/ja00095a051
- A.A. Agale, S.M. Janjal, S.T. Gaikwad and A.S. Rajbhoj, J. Cluster Sci., 28, 477 (2017); https://doi.org/10.1007/s10876-016-1118-4
- N. Basavegowda, K. Mishra and Y.R. Lee, RSC Adv., 4, 61660 (2014); https://doi.org/10.1039/C4RA11623B
- Y.P. Yew, K. Shameli, M. Miyake, N.B.B. Ahmad Khairudin, S.E.B. Mohamad, T. Naiki and K.X. Lee, Arab. J. Chem., 13, 2287 (2020); https://doi.org/10.1016/j.arabjc.2018.04.013
- M. Mahdavi, M. Ahmad, M. Haron, F. Namvar, B. Nadi, M. Rahman and J. Amin, Molecules, 18, 7533 (2013); https://doi.org/10.3390/molecules18077533
- A. Demir, R. Topkaya and A. Baykal, Polyhedron, 65, 282 (2013); https://doi.org/10.1016/j.poly.2013.08.041
- M. Hjiri, J. Mater. Sci. Mater. Electron., 31, 5025 (2020); https://doi.org/10.1007/s10854-020-03069-4
- A. Lassoued, M.S. Lassoued, B. Dkhil, S. Ammar and A. Gadri, Physica E, 101, 212 (2018); https://doi.org/10.1016/j.physe.2018.04.009
- L.E. Mathevula, L.L. Noto, B.M. Mothudi and M.S. Dhlamini, Physica B, 535, 258 (2018); https://doi.org/10.1016/j.physb.2017.07.053
- S.M.R. Shariatzadeh, M. Salimi, H. Fathinejad and A.H. Joshaghani, Int. J. Eng., 35, 1186 (2022); https://doi.org/10.5829/IJE.2022.35.06C.10
- F.N. Sayed and V. Polshettiwar, Sci. Rep., 5, 9733 (2015); https://doi.org/10.1038/srep09733
References
J. Tucek, L. Machala, S. Ono, A. Namai, M. Yoshikiyo, K. Imoto, H. Tokoro, S.-i. Ohkoshi and R. Zboril, Sci. Rep., 5, 15091 (2015); https://doi.org/10.1038/srep15091
X. Su, S. Chen and Z. Zhou, Appl. Surf. Sci., 258, 5712 (2012); https://doi.org/10.1016/j.apsusc.2012.02.067
K. Wongwailikhit and S. Horwongsakul, Mater. Lett., 65, 2820 (2011); https://doi.org/10.1016/j.matlet.2011.05.063
A. Lassenberger, T.A. Grünewald, P.D.J. van Oostrum, H. Rennhofer, H. Amenitsch, R. Zirbs, H.C. Lichtenegger and E. Reimhult, Chem. Mater., 29, 4511 (2017); https://doi.org/10.1021/acs.chemmater.7b01207
P. A. Calderón Bedoya, P. M. Botta, P. G. Bercoff, and M. A. Fanovich, J. Alloys Compd., 860, 157892 (2021); https://doi.org/10.1016/j.jallcom.2020.157892
P. Bhavani, C.H. Rajababu, M.D. Arif, I.V.S. Reddy and N.R. Reddy, J. Magn. Magn. Mater., 426, 459 (2017); https://doi.org/10.1016/j.jmmm.2016.09.049
A. Criveanu, F. Dumitrache, C. Fleaca, L. Gavrila-Florescu, I. Lungu, I.P. Morjan, V. Socoliuc and G. Prodan, Appl. Surf. Sci. Adv., 15, 100405 (2023); https://doi.org/10.1016/j.apsadv.2023.100405
G. Salazar-Alvarez, M. Muhammed and A.A. Zagorodni, Chem. Eng. Sci., 61, 4625 (2006); https://doi.org/10.1016/j.ces.2006.02.032
R. Tischendorf, M. Simmler, C. Weinberger, M. Bieber, M. Reddemann, F. Fröde, J. Lindner, H. Pitsch, R. Kneer, M. Tiemann, H. Nirschl and H.-J. Schmid, J. Aerosol Sci., 154, 105722 (2021); https://doi.org/10.1016/j.jaerosci.2020.105722
M.O. Besenhard, A.P. LaGrow, A. Hodzic, M. Kriechbaum, G. Bais, L. Panariello, K. Loizou, S. Damilos, M. Margarida Cruz, N.T.K. Thanh and A. Gavriilidis, Chem. Eng. J., 399, 125740 (2020); https://doi.org/10.1016/j.cej.2020.125740
R. Arbain, M. Othman and S. Palaniandy, Miner. Eng., 24, 1 (2011); https://doi.org/10.1016/j.mineng.2010.08.025
O.I. Kuntyi, A.R. Kytsya, I.P. Mertsalo, A.S. Mazur, G.I. Zozula, L.I. Bazylyak and R.V. Topchak, Colloid Polym. Sci., 297, 689 (2019); https://doi.org/10.1007/s00396-019-04488-4
R.A. Khaydarov, R.R. Khaydarov, O. Gapurova, Y. Estrin and T. Scheper, J. Nanopart. Res., 11, 1193 (2009); https://doi.org/10.1007/s11051-008-9513-x
A. Rani, G. Singh, A. Singh, U. Maqbool, G. Kaur and J. Singh, RSC Adv., 10, 5610 (2020); https://doi.org/10.1039/C9RA09510A
M.S. Jangale, N.D. Bhoge, G.M. Sonwane, A.A. Pund and B.K. Magare, J. Mol. Struct., 1308, 138033 (2024); https://doi.org/10.1016/j.molstruc.2024.138033
M.M. Mudgal, N. Birudukota and M.A. Doke, Int. J. Med. Chem., 2018, 2946730 (2018); https://doi.org/10.1155/2018/2946730
L.L. Brockunier, M.R. Candelore, M.A. Cascieri, Y. Liu, L. Tota, M.J. Wyvratt, M.H. Fisher, A.E. Weber and E.R. Parmee, Bioorg. Med. Chem. Lett., 11, 379 (2001); https://doi.org/10.1016/S0960-894X(00)00669-7
K. Bozorov, J. Zhao and H. A. Aisa, Bioorg. Med. Chem., 27, 3511 (2020); https://doi.org/10.1016/j.bmc.2019.07.005
R. Huisgen, Angew. Chem., 13, 604 (1963); https://doi.org/10.1002/ange.19630751304
M. Gauthier and G. Whitton, Polymers, 9, 540 (2017); https://doi.org/10.3390/polym9100540
V.V. Rostovtsev, L.G. Green, V.V. Fokin and K.B. Sharpless, Angew. Chem., 114, 2708 (2002); https://doi.org/10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0
F. Alonso, Y. Moglie and G. Radivoy, Acc. Chem. Res., 48, 2516 (2015); https://doi.org/10.1021/acs.accounts.5b00293
M. Chetia, A.A. Ali, D. Bhuyan, L. Saikia and D. Sarma, New J. Chem., 39, 5902 (2015); https://doi.org/10.1039/C5NJ00754B
G. Molteni, A.M. Ferretti, M.I. Trioni, F. Cargnoni and A. Ponti, New J. Chem., 43, 18049 (2019); https://doi.org/10.1039/C9NJ04690A
M.T. Reetz and W. Helbig, J. Am. Chem. Soc., 116, 7401 (1994); https://doi.org/10.1021/ja00095a051
A.A. Agale, S.M. Janjal, S.T. Gaikwad and A.S. Rajbhoj, J. Cluster Sci., 28, 477 (2017); https://doi.org/10.1007/s10876-016-1118-4
N. Basavegowda, K. Mishra and Y.R. Lee, RSC Adv., 4, 61660 (2014); https://doi.org/10.1039/C4RA11623B
Y.P. Yew, K. Shameli, M. Miyake, N.B.B. Ahmad Khairudin, S.E.B. Mohamad, T. Naiki and K.X. Lee, Arab. J. Chem., 13, 2287 (2020); https://doi.org/10.1016/j.arabjc.2018.04.013
M. Mahdavi, M. Ahmad, M. Haron, F. Namvar, B. Nadi, M. Rahman and J. Amin, Molecules, 18, 7533 (2013); https://doi.org/10.3390/molecules18077533
A. Demir, R. Topkaya and A. Baykal, Polyhedron, 65, 282 (2013); https://doi.org/10.1016/j.poly.2013.08.041
M. Hjiri, J. Mater. Sci. Mater. Electron., 31, 5025 (2020); https://doi.org/10.1007/s10854-020-03069-4
A. Lassoued, M.S. Lassoued, B. Dkhil, S. Ammar and A. Gadri, Physica E, 101, 212 (2018); https://doi.org/10.1016/j.physe.2018.04.009
L.E. Mathevula, L.L. Noto, B.M. Mothudi and M.S. Dhlamini, Physica B, 535, 258 (2018); https://doi.org/10.1016/j.physb.2017.07.053
S.M.R. Shariatzadeh, M. Salimi, H. Fathinejad and A.H. Joshaghani, Int. J. Eng., 35, 1186 (2022); https://doi.org/10.5829/IJE.2022.35.06C.10
F.N. Sayed and V. Polshettiwar, Sci. Rep., 5, 9733 (2015); https://doi.org/10.1038/srep09733