10.57647/IJIC.2026.1702.08

An Efficient, Solvent-Free Synthesis of Xanthene Derivatives Using Z-NTS@Cu as a Reusable and Eco- Friendly Nano-catalyst

Show Details XML PDF
  • Mohammad Reza Haghshenas1,
  • Seyed Mohammad Vahdat*1,
  • Hasan Tahermansouri1,
  • Behrooz Maleki2,
  1. Department of Chemistry, Am.c. Islamic Azad University, Amol, Iran
  2. Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran

Received: 2026-02-27

Revised: 2026-03-30

Accepted: 2026-04-18

Published in Issue 2026-06-30

Copyright (c) 2026 Mohammad Reza Haghshenas, Seyed Mohammad Vahdat, Hasan Tahermansouri, Behrooz Maleki (Author)

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

Haghshenas, M. R., Vahdat, S. M., Tahermansouri, H., & Maleki, B. (2026). An Efficient, Solvent-Free Synthesis of Xanthene Derivatives Using Z-NTS@Cu as a Reusable and Eco- Friendly Nano-catalyst. International Journal of Industrial Chemistry, 17(2). https://doi.org/10.57647/IJIC.2026.1702.08
Crossref
Scopus
Google Scholar
Europe PMC

PDF views: 7

Abstract

In this study, a green and efficient one-pot multi-component protocol was developed for synthesizing a wide range of xanthene derivatives using (Z-NTS@Cu) as an eco-friendly and recyclable Nano-catalyst. The reactions proceeded under solvent-free conditions, providing excellent yields. The heterogeneous catalyst was prepared via stepwise surface modification of zeolite, which serves as a high-surface-area support with functionalizable active sites. The zeolite was first modified with 3-aminopropyl triethoxysilane (APTES) to introduce amino groups, followed by anchoring of cyanuric chloride (TCT) as a triazine linker, and subsequent immobilization of thiosemicarbazide. This functionalization created nitrogen and sulfur donor sites capable of stable copper coordination. Comprehensive characterization of the catalyst was performed using FT-IR, XRD, SEM, TEM, BET, TGA, EDX-EDS, and EDX mapping analyses, confirming successful functionalization and uniform copper distribution. The synergistic effect between the zeolite framework and the copper-thiosemicarbazide complex contributed to high catalytic activity and selectivity in multi-component reactions. The catalyst’s heterogeneous nature allowed straightforward separation and reuse for up to six consecutive cycles without significant loss of efficiency. Importantly, the reactions proceeded under mild conditions, highlighting the catalyst’s practicality and environmentally benign profile. Overall, the Z-NTS@Cu nanocatalyst represents a sustainable, reusable, and highly effective system for the green synthesis of xanthene derivatives, combining high performance, ease of recovery, and minimal environmental impact. Its design demonstrates how functionalized zeolite-supported copper complexes can advance eco-friendly organic synthesis while maintaining operational simplicity and excellent catalytic outcomes. 

Keywords

  • Nanocatalyst,
  • Zeolite,
  • Green organic synthesis,
  • Xanthene
PDF

References

  1. Amiri MA, Younesi H, Aqmashhadi HK, Pasha GF, Asghari S, Tajbakhsh M. Efficient catalytic synthesis of xanthenes with copper immobilized on amine-modified NaY. Chem Methodol. 2024;8(1):1-22. https://doi.org/10.48309/chemm.2024.424058.1737
  2. Eissen M, Metzger JO, Schmidt E, Schneidewind U. 10 years after Rio—concepts on the contribution of chemistry to a sustainable development. Angew Chem Int Ed. 2002;41(3):414-436. https://doi.org/10.1002/1521-3773(20020201)41:3<414::AID-ANIE414>3.0.CO;2-N
  3. Beach ES, Cui Z, Anastas PT. Green chemistry: a design framework for sustainability. Energy Environ Sci. 2009;2(10):1038-1049. https://doi.org/10.1039/B904997P
  4. Mishra M, Sharma M, Dubey R, Kumari P, Ranjan V, Pandey J. Green synthesis interventions of pharmaceutical industries for sustainable development. Curr Res Green Sustain Chem. 2021;4:100174. https://doi.org/10.1016/j.crgsc.2021.100174
  5. Kurul F, Doruk B, Topkaya SN. Principles of green chemistry: building a sustainable future. Discover Chemistry. 2025;2(1):68. https://doi.org/10.1007/s44371-025-00152-9
  6. Meurig Thomas SJ. Design and applications of single-site heterogeneous catalysts: contributions to green chemistry, clean technology and sustainability. https://doi.org/10.1142/9781848169111_0001
  7. Yenare PP, Patare RD, Sonawane BP, Sanap KK. Green chemistry innovation: a systematic review on sustainable catalysis and its strategic future directions. Catal Sci Technol. 2025. https://doi.org/10.1039/D5CY00559K
  8. Yasin M, Khalid S, Yasir M, Ayub S. Advances in sustainable chemical process: catalysis, renewable, and water reduction. Indus J Biosci Res. 2025;3(1):174-184. https://doi.org/10.70749/ijbr.v3i1.479
  9. Chaltash F, Vahdat SM, Acevedo R, Ghanbari S, Qandalee M, Durán-Valle CJ, Lopez-Coca IM. Green synthesis of bis(indolyl)methane scaffolds as valuable biological materials catalyzed by Fe3O4/SiO2/PPA as a magnetic nanocatalyst. Int J Nano Dimens. 2025. https://doi.org/10.57647/ijnd-2026-1702-07
  10. Li X, Wang J, Zhang T, Yang S, Sun M, Qian X, Wang T, Zhao Y. Sustainable catalytic strategies for the transformation of plastic wastes into valued products. Chem Eng Sci. 2023;276:118729. https://doi.org/10.1016/j.ces.2023.118729
  11. Venkateswara Rao C, Tiruveedhi VB, Sudewi S, Wu HF, Pang MG, Gedda G. The role of green chemistry in achieving sustainability goals. In: Advances in Organic Waste Conversion Through Industrial Biotechnology. Cham: Springer Nature Switzerland; 2026. p. 469-494. https://doi.org/10.1007/978-3-032-11377-1_19
  12. Sultan Alqahtani A, Elbeltagi S. Advancing chemistry sustainably: from synthesis to benefits and applications of green synthesis. J Organomet Chem. 2025;1027:123508. https://doi.org/10.1016/j.jorganchem.2025.123508
  13. Lakhani P, Bhanderi D, Modi CK. Support materials impact on green synthesis and sustainable processing via heterogeneous catalysis. Discover Catal. 2024;1(1):2. https://doi.org/10.1007/s44358-024-00002-0
  14. Liang J, Liang Z, Zou R, Zhao Y. Heterogeneous catalysis in zeolites, mesoporous silica, and metal–organic frameworks. Adv Mater. 2017;29(30):1701139. https://doi.org/10.1002/adma.201701139
  15. Yu X, Williams CT. Recent advances in the applications of mesoporous silica in heterogeneous catalysis. Catal Sci Technol. 2022;12(19):5765-5794. https://doi.org/10.1039/D2CY01224D
  16. Pines H, Haag WO. Alumina: catalyst and support. I. Alumina, its intrinsic acidity and catalytic activity. J Am Chem Soc. 1960;82(10):2471-2483. https://doi.org/10.1021/ja01477a021
  17. Ndolomingo MJ, Bingwa N, Meijboom R. Review of supported metal nanoparticles: synthesis methodologies, advantages and application as catalysts. J Mater Sci. 2020;55(15):6195-6241. https://doi.org/10.1007/s10853-020-04415-x
  18. Salih AM. The purification of industrial wastewater to remove heavy metals and investigation into the use of zeolite as a remediation tool. https://doi.org/10.13140/RG.2.2.20752.76807
  19. Shamsaei E. Controllable growth of zeolitic imidazolate framework composite membranes for gas separation [doctoral dissertation]. Monash University. https://doi.org/10.4225/03/58b657b0d42c5
  20. Diab AS, Allam AA, Rudayni HA, Abukhadra MR. Zeolite-based materials for sulfate remediation: A review of structure-function insights, modification strategies, and sustainable water treatment applications. Mater Today Sustain. 2026;101308. https://doi.org/10.1016/j.mtsust.2026.101308
  21. Abinader Vasconcelos A, Len T, de Nazaré de Oliveira A, Farias da Costa AA, da Silva Souza AR, Ferreira da Costa CE, Luque R, da Rocha Filho GN, Rodrigues Noronha RC, Santos do Nascimento LA. Zeolites: A theoretical and practical approach with uses in (bio)chemical processes. Appl Sci. https://doi.org/10.3390/app13031897
  22. Zhang Q, Gao S, Yu J. Metal sites in zeolites: synthesis, characterization, and catalysis. Chem Rev. 2023;123(9):6039-6106. https://doi.org/10.1021/acs.chemrev.2c00315
  23. Wang Y, Wang C, Wang L, Wang L, Xiao FS. Zeolite fixed metal nanoparticles: New perspective in catalysis. Acc Chem Res. 2021;54(11):2579-2590. https://doi.org/10.1021/acs.accounts.1c00054
  24. Wu D, Yang M, Yu J, Dyballa M, Yang P, Li M, Hou G, Hunger M, Dai W. The role of adsorption and diffusion in improving the selectivity and reactivity of zeolite catalysts. Chem Soc Rev. 2025;54(20):9192-9244. https://doi.org/10.1039/D4CS01253F
  25. Dai J, Zhang H. Recent advances in catalytic confinement effect within micro/meso-porous crystalline materials. Small. 2021;17(22):2005334. https://doi.org/10.1002/smll.202005334
  26. Zormpa F, Treu P, Saraçi E. Advancing biomass valorization with zeolite catalysts: Focus on oxidative transformations. Sustain Chem Environ. 2025;10:100249. https://doi.org/10.1016/j.sce.2025.100249
  27. Chu D, Ma J, Liu Q, Fu J, Yin H. Effects of zeolite porosity and acidity on catalytic conversion of carbohydrates to bio-based chemicals: A review. Catal Sci Technol. 2024;14(24):6980-7001. https://doi.org/10.1039/D4CY00944F
  28. Gunda NS, Singh M, Norman L, Kaur K, Mitra SK. Optimization and characterization of biomolecule immobilization on silicon substrates using (3-aminopropyl) triethoxysilane (APTES) and glutaraldehyde linker. Appl Surf Sci. 2014;305:522-530. https://doi.org/10.1016/j.apsusc.2014.03.189
  29. Ismael BM, El-Nawawy MA, Gomaa HA, El-Gammal O. Divalent transition metal complexes of multidentate nitrogen, oxygen and sulfur containing ligand: Design, spectroscopic, theoretical molecular modeling and antioxidant like activity. Egypt J Chem. 2022;65(9):639-55. https://doi.org/10.21608/ejchem.2022.112663.5125
  30. Song Y, Gai X, Ju H, Han Z, Zhu Y, Xi D, et al. Michael-addition reaction triggering sensitive and facile detection of glutathione employing LSPR-photonic crystals. Talanta. 2026;297:128656. https://doi.org/10.1016/j.talanta.2025.128656
  31. Liu R, Fu Y, Wu F, Liu F, Zhang JJ, Yang L, et al. Modular synthesis of structurally diverse azulene-embedded polycyclic aromatic hydrocarbons by Knoevenagel-type condensation. Angew Chem Int Ed. 2023;62(21):e202219091. https://doi.org/10.1002/anie.202219091
  32. Meftah T, Zerafat MM. Nitrate removal from drinking water using organo-silane modified natural nano-zeolite. Int J Nanosci Nanotechnol. 2016;12(4):223-32. https://doi.org/10.7508/ijnnt.2016.04.003
  33. Barquist KN. Synthesis and environmental adsorption applications of functionalized zeolites and iron oxide/zeolite composites [dissertation]. Iowa (IA): The University of Iowa; 2009. https://doi.org/10.17077/etd.9aa8vru4
  34. Taghartapeh MR, Pesyan NN, Rashidnejad H, Khavasi HR, Soltani A. Synthesis, spectroscopic and photophysical studies of xanthene derivatives. J Mol Struct. 2017;1149:862-73. https://doi.org/10.1016/j.molstruc.2017.08.053
  35. Mileski TC. Aplicação de corantes benzazólicos fluorescentes por ESIPT para a revelação de manchas de sangue em cenas de crime e a síntese do luminol. https://doi.org/10.25358/openscience-1143
  36. Ghashghaei R, Ghassamipour S. A green procedure for synthesis of xanthene derivatives: Micellar solution of sodium dodecylphosphonate catalyzes condensation reaction of aldehydes and β-naphthol in aqueous media. 2014. https://doi.org/10.13140/RG.2.2.27538.89289
  37. Pirouzmand M, Gharehbaba AM, Ghasemi Z. Synthesis of xanthene derivatives using template-containing Zn/MCM-41 as a green and reusable catalyst: Effect of the template. J Mex Chem Soc. 2016;60(4):183-7. https://doi.org/10.29356/jmcs.v60i4.122
  38. Sadjadi S. Efficient synthesis of xanthene derivatives in aqueous media in the presence of Cu-anchored furfural imine-functionalized halloysite. https://doi.org/10.13140/RG.2.2.22868.81284
  39. Sadjadi S, Heravi MM, Daraie M. Cyclodextrin nanosponges: A potential catalyst and catalyst support for synthesis of xanthenes. Res Chem Intermed. 2017;43(2):843-57. https://doi.org/10.1007/s11164-016-2687-8
  40. Sudha S, Pasha MA. Ultrasound assisted synthesis of tetrahydrobenzo[c]xanthene-11-ones using CAN as catalyst. Ultrason Sonochem. 2012;19(5):994-998. https://doi.org/10.1016/j.ultsonch.2012.01.001
  41. Li J, Tang W, Lu L, Su W. Strontium triflate catalyzed one-pot condensation of β-naphthol, aldehydes and cyclic 1,3-dicarbonyl compounds. Tetrahedron Lett. 2008;49(50):7117-7120. https://doi.org/10.1016/j.tetlet.2008.10.046
  42. Alizadeh MH, Kermani T, Tayebee R. A method for the acetylation of alcohols catalyzed by heteropolyoxometallates. Monatsh Chem. 2007;138(2):165-170. https://doi.org/10.1007/s00706-006-0573-2
  43. Sadjadi S, Abedian-Dehaghani N, Heydari A, Heravi MM. Chitosan bead containing metal–organic framework encapsulated heteropolyacid as an efficient catalyst for cascade condensation reaction. Sci Rep. 2023;13(1):2797. https://doi.org/10.1038/s41598-023-29548-2
  44. Kumar S, Dubey S, Saxena N, Awasthi SK. (NH4)2Ce(NO3)6 as an inexpensive, eco-friendly, efficient catalyst for the synthesis of 5-substituted 1H-tetrazoles from nitriles. Tetrahedron Lett. 2014;55(44):6034-6038. https://doi.org/10.1016/j.tetlet.2014.09.010