Abstract
Graphene oxide (GO) and transition metal complexes are two well-studied systems owing to their diverse applications and superior properties. Herein, GO/Fe3O4 nanostructure was prepared and used as a support for grafting Schiff base-Cu complex. This novel nanocatalyst was synthesized through modification of GO using Schiff base-Cu complex [GO/Fe3O4/Schiff base-Cu] being an eco-friendly, convenient and cost-effective procedure. The product was studied by various characterization techniques whose results revealed that the copper complex was grafted on the surface of the magnetic graphene oxide. The obtained nanocomposite shows chemical and thermal stabilities, as well as significant catalytic behavior. GO/Fe3O4/Schiff base-Cu nanocomposite was investigated as an efficient catalyst in the reduction of 4-nitrophenol and dyes, including methylene blue (MB) and Congo red (CR) with sodium borohydride in room temperature and aqueous solution by checking the reaction progress via visible–ultraviolent spectroscopy. Also, the catalytic activity of the novel nanocatalyst was evaluated in Knoevenagel condensation and Michael-type addition for the preparation of 2-amino 4H-chromene in ethanol/water green solvent at the temperature of 60 °C. The results showed that the synthesized nanocatalyst isolated magnetically can be reused for 4 times with no remarkable loss in the product yield. The synthesis method employed here demonstrated mainly the advantages of being ecofriendly and simple, excellent yields and high efficiency, usage of non-toxic solvent, as well as easiness of product isolation using ethanol.
Similar content being viewed by others
Data availability
The data that support the findings of this study are included in this published article.
References
C.Y. Lee, O.K. Farha, B.J. Hong, A.A. Sarjeant, S.T. Nguyen, J.T. Hupp, J. Am. Chem. Soc. 133, 15858 (2011)
R. Sharma, A. Puri, Y. Monga, A. Adholeya, Sep. Purif. Technol. 127, 121 (2014)
V. Yadav, V. Chavan, Appl. Organomet. Chem. 37, 7025 (2023)
R. Sharma, A. Puri, A. Kumar, Y. Monga, G. Gaba, A. Adholeya, Sep. Sci. Technol. 49, 709 (2014)
B. Tian, T. Wang, R. Dong, S. Bao, F. Yang, J. Zhang, Appl. Catal. B 147, 22 (2014)
K.S. Shin, Y.K. Cho, J.-Y. Choi, K. Kim, Appl. Catal. A: Gen. 413, 170 (2012)
M. Masteri-Farahani, S. Mirshekar, Colloids Surf. A Physicochem. Eng. 538, 387 (2018)
M. Lashanizadegan, K. Nikoofar, A. Aghaei, F. Mehrikaram, H. Mirzazadeh, Solid State Sci. 95, 105937 (2019)
I. Ali, A.A. Al-Arfaj, T.A. Saleh, J. Mol. Liq. 304, 112376 (2020)
R. Sharma, A. Pandey, S. Gulati, Polyhedron 45, 86 (2012)
F. Nemati, M.M. Heravi, R.S. Rad, Chin. J. Catal. 33, 1825 (2012)
R. Sharma, Y. Monga, A. Puri, J. Mol. Catal. A Chem. 393, 84 (2014)
R.K. Layek, A.K. Nandi, Polymer 54, 5087 (2013)
T. Huang, M. Yan, K. He, Z. Huang, G. Zeng, A. Chen, M. Peng, H. Li, L. Yuan, G. Chen, J. Colloid Interface Sci. 543, 43 (2019)
N. Pandey, C. Tewari, S. Dhali, B.S. Bohra, S. Rana, S. Mehta, S. Singhal, A. Chaurasia, N.G. Sahoo, J. Thermoplast. Compos. Mater. 34, 55 (2021)
A. Maleki, R. Paydar, RSC Adv. 5, 33177 (2015)
L.M. Kumar, P. Mishra, B.R. Bhat, J. Saudi Chem. Soc. 23, 307 (2019)
D. Gautam, S. Hooda, J. Chem. Eng. Data 65, 4052 (2020)
A. Sherlala, A. Raman, M. Bello, A. Asghar, Chemosphere 193, 1004 (2018)
N. Seyedi, K. Saidi, H. Sheibani, Catal. Lett. 148, 277 (2018)
R. Kottappara, S.C. Pillai, B.K. Vijayan, Inorg. Chem. Commun. 121, 108181 (2020)
C. Xia, X. Jin, A. Parandoust, R. Sheibani, Z. Khorsandi, N. Montazeri, Y. Wu, Q. Van Le, Int. J. Biol. Macromol. 239, 124135 (2023)
S.A. Lawrence, Amines: Synthesis, Properties and Applications (Cambridge University Press, Cambridge, 2004)
R.A. Sheldon, H. Van Bekkum, Fine Chemicals Through Heterogeneous Catalysis (Wiley, New York, 2008)
K.C. Das, S.S. Dhar, J. Mater. Sci. Eng. B 263, 114841 (2021)
S. Dayan, Bayar Üniv. Fen Bilim. Derg. 16, 285 (2020)
S. Akocak, B. Şen, N. Lolak, A. Şavk, M. Koca, S. Kuzu, F. Şen, Nanostruct. Nanoobjects 11, 25 (2017)
M.P. Lati, F. Shirini, M. Alinia-Asli, M.A. Rezvani, J. Nanosci. Nanotechnol. 20, 973 (2020)
N. Monadi, H. Davoodi, M. Aghajani, React. Kinet. Mech. Catal. 129, 1 (2020)
J. Zhang, X. Hu, Z. Zhou, J. Chem. Chem. Eng. 34, 47 (2015)
H. Ebrahimiasl, D. Azarifar, M. Mohammadi, H. Keypour, Res. Chem. Intermed. 47, 683 (2021)
S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48, 3299 (2007)
A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)
B. Beck, S. Hess, A. Dömling, Bioorgan. Med. Chem. Lett. 10, 1701 (2000)
M.S. Dastjerdy, N. Monadi, Appl. Organomet. Chem. 37, e6931 (2023)
F. Rahmatpour, M. Kosari, N. Monadi, J. Mol. Struct. 1253, 132102 (2022)
D.C. Marcano, D.V. Kosynkin, J.M. Berlin, A. Sinitskii, Z. Sun, A. Slesarev, L.B. Alemany, W. Lu, J.M. Tour, ACS Nano 4, 4806 (2010)
X. Yang, T. Zhou, B. Ren, Z. Shi, A. Hursthouse, J. Anal. Methods Chem. 2017, 1 (2017)
M. Bagherzadeh, H. Karimi, M. Amini, J. Coord. Chem. 70, 2986 (2017)
M. Aghajani, N. Monadi, J. Iran. Chem. Soc. 14, 963 (2017)
A. Zarnegaryan, Z. Pahlevanneshan, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammdpoor-Baltork, J. Iran. Chem. Soc. 16, 747 (2019)
L. Nirumand, S. Farhadi, New J. Chem. 47, 4845 (2023)
A. Zarnegaryan, Z. Dehbanipour, Appl. Surf. Sci. Adv. 4, 100074 (2021)
X. Li, J. Feng, Y. Du, J. Bai, H. Fan, H. Zhang, Y. Peng, F. Li, J. Mater. Chem. 3, 5535 (2015)
B. Jaleh, A. Khalilipour, H. Safdar, M. Niyaifar, M. Nasrollahzadeh, J. Mater. Sci. Mater. Electron. 28, 4974 (2017)
M. Raghu, K.Y. Kumar, M. Prashanth, B. Prasanna, R. Vinuth, C.P. Kumar, J. Water Process Eng. 17, 22 (2017)
G. Wang, G. Chen, Z. Wei, X. Dong, M. Qi, Mater. Chem. Phys. 141, 997 (2013)
J.M. Khurana, B. Nand, P. Saluja, Tetrahedron Lett. 66, 5637 (2010)
D. Kumar, V.B. Reddy, B.G. Mishra, R. Rana, M.N. Nadagouda, R.S. Varma, Tetrahedron 63, 3093 (2007)
F. Kalantari, S. Rezayati, A. Ramazani, H. Aghahosseini, K. Ślepokura, T. Lis, A.C.S. Appl, Nano Mater. 5, 1783 (2022)
H. Ebrahimiasl, D. Azarifar, Appl. Organomet. Chem. 34, e5359 (2020)
N. Divsalar, N. Monadi, M. Tajbaksh, J. Nanostruct. 6, 312 (2016)
M. Aghajani, N. Monadi, J. Chin. Chem. Soc. 66, 775 (2019)
J. Safari, Z. Zarnegar, M. Heydarian, J. Taibah Univ. Sci. 7, 17 (2013)
P. Mohammadi, H. Sheibani, Mater. Chem. Phys. 228, 140 (2019)
G.T. Pawar, R.R. Magar, M.K. Lande, Polycycl. Aromat. Compd. 38, 75 (2018)
S. Siddiqui, Z.N. Siddiqui, Appl. Organomet. Chem. 33, e5161 (2019)
Y. Xu, X. Shi, R. Hua, R. Zhang, Y. Yao, B. Zhao, T. Liu, J. Zheng, G. Lu, Appl. Catal. B Environ. 260, 118142 (2020)
N. Sahiner, S. Sagbas, N. Aktas, RSC Adv. 5, 18183 (2015)
R.K. Sharma, P. Jeevanandam, Ceram. Int. 39, 3337 (2013)
M. Nasrollahzadeh, S.M. Sajadi, A. Rostami-Vartooni, M. Bagherzadeh, R. Safari, J. Mol. Catal. A Chem. 400, 22 (2015)
M. Nasrollahzadeh, M. Bagherzadeh, H. Karimi, J. Colloid Interface Sci. 465, 271 (2016)
P. Sudhakar, H. Soni, J. Environ. Chem. Eng. 6, 28 (2018)
S.R. Thakare, V.R. Mate, K. Urkude, S.B. Gawande, FlatChem 22, 100179 (2020)
M.H. Oueslati, L. BenTahar, A.H. Harrath, Green Chem. Lett. Rev. 13, 18 (2020)
A. Lajevardi, M.T. Yaraki, A. Masjedi, A. Nouri, M.H. Sadr, J. Mol. Liq. 276, 371 (2019)
T. Varadavenkatesan, R. Selvaraj, R. Vinayagam, Mater. Today Proc. 23, 39 (2020)
M. Nasrollahzadeh, Z. Issaabadi, S.M. Sajadi, Compos. B Eng. 166, 112 (2019)
M.K. Indana, B.R. Gangapuram, R. Dadigala, R. Bandi, V. Guttena, J. Anal. Sci. Technol. 7, 1 (2016)
M. Nasrollahzadeh, Z. Issaabadi, S.M. Sajadi, RSC Adv. 8, 3723 (2018)
Acknowledgements
The authors acknowledge the University of Mazandaran Research Councils for financial support of this research project.
Funding
This research received no specific grant from any funding agency. This work was not supported by any funding.
Author information
Authors and Affiliations
Contributions
Niaz Monadi was involved in supervision, writing—original draft, writing review and editing. Shima Khajevand Khosheli performed the data collection and methodology.
Corresponding author
Ethics declarations
Conflict of interest
There are no conflict of interest with this research work.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Khajevand Khosheli, S., Monadi, N. Design of copper complex anchored on magnetic graphene oxide as a novel, recoverable and environmentally friendly nanocatalyst for treating organic pollutants and one-pot synthesis of chromenes. J IRAN CHEM SOC 21, 1369–1388 (2024). https://doi.org/10.1007/s13738-024-03004-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-024-03004-y