{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T23:13:26Z","timestamp":1789168406191,"version":"build-2803163510"},"reference-count":57,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2022,4,25]],"date-time":"2022-04-25T00:00:00Z","timestamp":1650844800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2022,4,25]],"date-time":"2022-04-25T00:00:00Z","timestamp":1650844800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Sci Rep"],"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In the present research, a recyclable catalyst has been prepared via a simple approach using chitosan as a linear polysaccharide. This paper reports the synthesis of novel copper(II) complex of 5-phenyl-1<jats:italic>H<\/jats:italic>-tetrazole immobilized on magnetic chitosan (MCS@PhTet@Cu(II)) as an effective catalyst. Transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), vibrating sample magnetometer (VSM), Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), and inductively coupled plasma mass spectrometry (ICP-MS) techniques were applied for the characterization of the catalyst. The catalytic activity of MCS@PhTet@Cu(II) was evaluated in the ultrasound-assisted synthesis of 3-imino-2-phenylisoindolin-1-one derivatives via the reaction between benzoyl chloride and arylcyanamides in ethanol at ambient temperature. Utilizing a wide variety of arylcyanamides under mild conditions, no use of toxic organic solvents, moderate reaction time, high yields along with catalyst excellent reusability and easy separation of the products without any tedious separation techniques, made this method a novel and simple process. The resulting heterogeneous catalyst showed valuable advantages such as easier work-up, better stability, and greater separation ability using an external magnet. The catalyst showed high efficacy and recyclability even after five cycles with no significant loss of its efficacy. The present methodology provides a path for the preparation of structurally diverse heterocyclic compounds, which may exhibit important biological activity.<\/jats:p>","DOI":"10.1038\/s41598-022-10591-4","type":"journal-article","created":{"date-parts":[[2022,4,25]],"date-time":"2022-04-25T12:04:05Z","timestamp":1650888245000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Magnetic chitosan stabilized Cu(II)-tetrazole complex: an effective nanocatalyst for the synthesis of 3-imino-2-phenylisoindolin-1-one derivatives under ultrasound irradiation"],"prefix":"10.1038","volume":"12","author":[{"given":"Mahmoud","family":"Nasrollahzadeh","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nasrin","family":"Shafiei","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasin","family":"Orooji","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2022,4,25]]},"reference":[{"issue":"23","key":"10591_CR1","doi-asserted-by":"publisher","first-page":"14555","DOI":"10.1021\/acs.chemrev.1c00611","volume":"121","author":"F-G Zhang","year":"2021","unstructured":"Zhang, F.-G., Chen, Z., Tang, X. & Ma, J.-A. Triazines: Syntheses and inverse electron-demand diels-alder reactions. Chem. Rev. 121(23), 14555\u201314593 (2021).","journal-title":"Chem. Rev."},{"issue":"1","key":"10591_CR2","doi-asserted-by":"publisher","first-page":"498","DOI":"10.1021\/acs.joc.1c02521","volume":"87","author":"T Han","year":"2022","unstructured":"Han, T. et al. Synthesis of difluoromethylated pyrazoles by the [3 + 2] cycloaddition reaction of difluoroacetohydrazonoyl bromides. J. Org. Chem. 87(1), 498\u2013511 (2022).","journal-title":"J. Org. Chem."},{"issue":"22","key":"10591_CR3","doi-asserted-by":"publisher","first-page":"8942","DOI":"10.1021\/acs.orglett.1c03431","volume":"23","author":"T-F Xiao","year":"2021","unstructured":"Xiao, T.-F. et al. Dehydrogenation\/(3+2) cycloaddition of saturated aza-heterocycles via merging organic photoredox and Lewis acid catalysis. Org. Lett. 23(22), 8942\u20138946 (2021).","journal-title":"Org. Lett."},{"issue":"7","key":"10591_CR4","doi-asserted-by":"publisher","first-page":"1561","DOI":"10.1021\/acs.orglett.2c00253","volume":"24","author":"J Wang","year":"2022","unstructured":"Wang, J. et al. Palladium-catalyzed asymmetric (3 + 2) cycloaddition of vinyl epoxides with substituted propiolates: Enantioselective formation of 2,3,4-trisubstituted 2,3-dihydrofurans. Org. Lett. 24(7), 1561\u20131565 (2022).","journal-title":"Org. Lett."},{"issue":"1","key":"10591_CR5","doi-asserted-by":"publisher","first-page":"464","DOI":"10.1021\/acs.joc.1c02484","volume":"87","author":"J Zheng","year":"2022","unstructured":"Zheng, J., Meng, S.-Y., Wang, Q.-R. & Wang, J.-M. Synthesis of antimicrobial benzo[1,2,4]triazoloazepinium salts and tetrahydronaphtho[1,2-e][1,2,4]triazines by polar [3+ + 2] and [4 + 2]-cycloaddition reactions. J. Org. Chem. 87(1), 464\u2013478 (2022).","journal-title":"J. Org. Chem."},{"key":"10591_CR6","doi-asserted-by":"publisher","first-page":"115819","DOI":"10.1016\/j.carbpol.2019.115819","volume":"232","author":"N Motahharifar","year":"2020","unstructured":"Motahharifar, N., Nasrollahzadeh, M., Taheri-Kafrani, A., Varma, R. S. & Shokouhimehr, M. Magnetic chitosan-copper nanocomposite: A plant assembled catalyst for the synthesis of amino-and N-sulfonyl tetrazoles in eco-friendly media. Carbohydr. Polym. 232, 115819 (2020).","journal-title":"Carbohydr. Polym."},{"issue":"44","key":"10591_CR7","doi-asserted-by":"publisher","first-page":"152464","DOI":"10.1016\/j.tetlet.2020.152464","volume":"61","author":"M Shanmugasundaram","year":"2020","unstructured":"Shanmugasundaram, M., Senthilvelan, A. & Kore, A. R. Highly regioselective 1,3-dipolar cycloaddition of 3\u2019-O-propargyl guanosine with nitrile oxide: An efficient method for the synthesis of guanosine containing isoxazole moiety. Tetrahedron Lett. 61(44), 152464 (2020).","journal-title":"Tetrahedron Lett."},{"key":"10591_CR8","doi-asserted-by":"publisher","first-page":"131922","DOI":"10.1016\/j.tet.2021.131922","volume":"81","author":"Y-T Tian","year":"2021","unstructured":"Tian, Y.-T., Zhang, F.-G. & Ma, J.-A. Et3N-catalyzed direct cycloaddition reaction of allenoates with acceptor diazo compounds. Tetrahedron 81, 131922 (2021).","journal-title":"Tetrahedron"},{"issue":"52","key":"10591_CR9","doi-asserted-by":"publisher","first-page":"152664","DOI":"10.1016\/j.tetlet.2020.152664","volume":"61","author":"KDD Kartikey","year":"2020","unstructured":"Kartikey, K. D. D., Reddy, M. S. & Chowhan, L. R. Isatin N, N\u2032-cyclic azomethine imine 1,3-dipole mediated regio and diastereoselective synthesis of isoxazole-containing spirooxindoles by an abnormal [3 + 2] cycloaddition. Tetrahedron Lett. 61(52), 152664 (2020).","journal-title":"Tetrahedron Lett."},{"key":"10591_CR10","doi-asserted-by":"publisher","first-page":"2831","DOI":"10.1021\/acs.orglett.8b00780","volume":"20","author":"S Wu","year":"2018","unstructured":"Wu, S., Wu, X., Fu, C. & Ma, S. Rhodium(III)-catalyzed C-H functionalization in water for isoindolin-1-one synthesis. Org. Lett. 20, 2831\u20132834 (2018).","journal-title":"Org. Lett."},{"key":"10591_CR11","doi-asserted-by":"publisher","first-page":"832","DOI":"10.1021\/ol3035142","volume":"15","author":"S Fustero","year":"2013","unstructured":"Fustero, S., Ibanez, I., Barrio, P., Maestro, M. A. & Catalan, S. Gold-catalyzed intramolecular hydroamination of o-alkynylbenzyl carbamates: A route to chiral fluorinated isoindoline and isoquinoline derivatives. Org. Lett. 15, 832\u2013835 (2013).","journal-title":"Org. Lett."},{"key":"10591_CR12","doi-asserted-by":"publisher","first-page":"5810","DOI":"10.1039\/C9CS00478E","volume":"49","author":"Y Wang","year":"2020","unstructured":"Wang, Y., Zhang, W.-X. & Xi, Z. Carbodiimide-based synthesis of N-heterocycles: moving from two classical reactive sites to chemical bond breaking\/forming reaction. Chem. Soc. Rev. 49, 5810\u20135849 (2020).","journal-title":"Chem. Soc. Rev."},{"key":"10591_CR13","doi-asserted-by":"publisher","first-page":"1176","DOI":"10.1039\/C4GC01822B","volume":"17","author":"F Aric\u00f2","year":"2015","unstructured":"Aric\u00f2, F., Evaristo, S. & Tundo, P. Synthesis of five-and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases. Green Chem. 17, 1176\u20131185 (2015).","journal-title":"Green Chem."},{"issue":"22","key":"10591_CR14","doi-asserted-by":"publisher","first-page":"8921","DOI":"10.1021\/acs.orglett.1c03413","volume":"23","author":"X Xie","year":"2021","unstructured":"Xie, X. & Sun, J. [4+3]-Cycloaddition reaction of sulfilimines with cyclobutenones: Access to benzazepinones. Org. Lett. 23(22), 8921\u20138925 (2021).","journal-title":"Org. Lett."},{"issue":"24","key":"10591_CR15","doi-asserted-by":"publisher","first-page":"7107","DOI":"10.1016\/j.electacta.2008.05.010","volume":"53","author":"I Fechete","year":"2008","unstructured":"Fechete, I. & Jouikov, V. Double decarbonylation of phthalimide revisited: A facile cathodic synthesis of isoindoline. Electrochim. Acta. 53(24), 7107\u20137110 (2008).","journal-title":"Electrochim. Acta."},{"key":"10591_CR16","doi-asserted-by":"publisher","first-page":"18401","DOI":"10.1039\/C4RA15379K","volume":"5","author":"R Csonka","year":"2015","unstructured":"Csonka, R., Speier, G. & Kaizer, J. Isoindoline-derived ligands and applications. RSC Adv. 5, 18401\u201318419 (2015).","journal-title":"RSC Adv."},{"key":"10591_CR17","doi-asserted-by":"publisher","first-page":"1696","DOI":"10.1021\/ol300250h","volume":"14","author":"R Mor\u00e1n-Ramallal","year":"2012","unstructured":"Mor\u00e1n-Ramallal, R. et al. Dynamic kinetic resolution of 1,3-dihydro-2H-isoindole-1-carboxylic acid methyl ester: Asymmetric transformations toward isoindoline carbamates. Org. Lett. 14, 1696\u20131699 (2012).","journal-title":"Org. Lett."},{"key":"10591_CR18","doi-asserted-by":"publisher","first-page":"1571","DOI":"10.1007\/s00706-015-1449-0","volume":"146","author":"S Shen","year":"2015","unstructured":"Shen, S., Chen, Y., Lei, M. & Hu, L. Catalyst-free synthesis of isoindolin-1-imine derivatives via multi-component reaction in water medium. Monatsh. Chem. 146, 1571\u20131580 (2015).","journal-title":"Monatsh. Chem."},{"key":"10591_CR19","doi-asserted-by":"publisher","first-page":"2944","DOI":"10.1021\/jo402776u","volume":"79","author":"BS Bhakuni","year":"2014","unstructured":"Bhakuni, B. S. et al. KOtBu-mediated synthesis of dimethylisoindolin-1-ones and dimethyl-5-phenylisoindolin-1-ones: selective C-C coupling of an unreactive tertiary sp3 C-H bond. J. Org. Chem. 79, 2944\u20132954 (2014).","journal-title":"J. Org. Chem."},{"key":"10591_CR20","doi-asserted-by":"publisher","first-page":"2288","DOI":"10.1002\/adsc.201200212","volume":"354","author":"B Liu","year":"2012","unstructured":"Liu, B., Li, Y., Jiang, H., Yin, M. & Huang, H. Palladium-catalyzed C-C coupling of aryl halides with isocyanides: An alternative method for the stereoselective synthesis of (3E)-(imino) isoindolin-1-ones and (3E)-(imino) thiaisoindoline 1,1-dioxides. Adv. Synth. Catal. 354, 2288\u20132300 (2012).","journal-title":"Adv. Synth. Catal."},{"key":"10591_CR21","doi-asserted-by":"publisher","first-page":"1279","DOI":"10.1055\/s-0031-1289749","volume":"44","author":"M-H Larraufie","year":"2012","unstructured":"Larraufie, M.-H. et al. The cyanamide moiety, synthesis and reactivity. Synthesis (Stuttg). 44, 1279\u20131292 (2012).","journal-title":"Synthesis (Stuttg)."},{"issue":"17","key":"10591_CR22","doi-asserted-by":"publisher","first-page":"5282","DOI":"10.1021\/acs.orglett.8b02225","volume":"20","author":"JN Ayres","year":"2018","unstructured":"Ayres, J. N. et al. Synthesis and reactivity of N-allenyl cyanamides. Org. Lett. 20(17), 5282\u20135285 (2018).","journal-title":"Org. Lett."},{"key":"10591_CR23","doi-asserted-by":"publisher","first-page":"6","DOI":"10.1007\/s12039-021-02001-5","volume":"134","author":"VB Pendem","year":"2022","unstructured":"Pendem, V. B., Tamminana, R. & Nannapaneni, M. Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions. J. Chem. Sci. 134, 6 (2022).","journal-title":"J. Chem. Sci."},{"issue":"4","key":"10591_CR24","doi-asserted-by":"publisher","first-page":"615","DOI":"10.3390\/molecules22040615","volume":"22","author":"MR Ranga Prabhath","year":"2017","unstructured":"Ranga Prabhath, M. R., Williams, L., Bhat, S. V. & Sharma, P. Recent advances in cyanamide chemistry: Synthesis and applications. Molecules 22(4), 615 (2017).","journal-title":"Molecules"},{"key":"10591_CR25","doi-asserted-by":"publisher","first-page":"27631","DOI":"10.1039\/C8RA04368J","volume":"8","author":"M Nasrollahzadeh","year":"2018","unstructured":"Nasrollahzadeh, M., Issaabadi, Z. & Sajadi, S. M. Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water. RSC Adv. 8, 27631 (2018).","journal-title":"RSC Adv."},{"key":"10591_CR26","doi-asserted-by":"publisher","first-page":"1387","DOI":"10.1007\/s11178-005-0030-4","volume":"40","author":"DD Nekrasov","year":"2004","unstructured":"Nekrasov, D. D. Synthesis and chemical transformations of mono-and disubstituted cyanamides. Russ. J. Org. Chem. 40, 1387\u20131402 (2004).","journal-title":"Russ. J. Org. Chem."},{"key":"10591_CR27","doi-asserted-by":"publisher","first-page":"1195","DOI":"10.1016\/0040-4020(75)85056-3","volume":"31","author":"G Simig","year":"1975","unstructured":"Simig, G., Lempert, K., Tam\u00e1s, J. & Czira, G. The reaction of N-cyanoamines with 1-(t-butyl)-3, 3-diphenylaziridinone: A general method for the synthesis of 1-alkyl-, 1-aralkyl-and 1-aryl-5, 5-diphenylhydantoins and-glycocyamidines. Tetrahedron 31, 1195\u20131200 (1975).","journal-title":"Tetrahedron"},{"key":"10591_CR28","doi-asserted-by":"publisher","first-page":"123","DOI":"10.1016\/j.ultsonch.2009.05.011","volume":"17","author":"R Kuppa","year":"2010","unstructured":"Kuppa, R. & Moholkar, V. S. Physical features of ultrasound-enhanced heterogeneous permanganate oxidation. Ultrason. Sonochem. 17, 123\u2013131 (2010).","journal-title":"Ultrason. Sonochem."},{"issue":"3","key":"10591_CR29","doi-asserted-by":"publisher","first-page":"415","DOI":"10.2174\/1570179054368509","volume":"2","author":"J-T Li","year":"2005","unstructured":"Li, J.-T., Wang, S.-X., Chen, G.-F. & Li, T.-S. Some Applications of ultrasound irradiation in organic synthesis. Curr. Org. Synth. 2(3), 415\u2013436 (2005).","journal-title":"Curr. Org. Synth."},{"issue":"24","key":"10591_CR30","doi-asserted-by":"publisher","first-page":"10284","DOI":"10.1021\/acs.nanolett.1c03381","volume":"21","author":"H Liu","year":"2021","unstructured":"Liu, H. et al. Atomically dispersed Cu catalyst for efficient chemoselective hydrogenation reaction. Nano Lett. 21(24), 10284\u201310291 (2021).","journal-title":"Nano Lett."},{"key":"10591_CR31","doi-asserted-by":"publisher","first-page":"100609","DOI":"10.1016\/j.mtphys.2022.100609","volume":"22","author":"C Zhao","year":"2022","unstructured":"Zhao, C., Xi, M., Huo, J., He, C. & Fu, L. Electro-reduction of N2 on nanostructured materials and the design strategies of advanced catalysts based on descriptors. Mater. Today Phys. 22, 100609 (2022).","journal-title":"Mater. Today Phys."},{"issue":"3","key":"10591_CR32","doi-asserted-by":"publisher","first-page":"133","DOI":"10.1080\/02603594.2021.1895127","volume":"41","author":"M Khatami","year":"2021","unstructured":"Khatami, M. & Iravani, S. Green and eco-friendly synthesis of nanophotocatalysts: An overview. Comments Inorg. Chem. 41(3), 133\u2013187 (2021).","journal-title":"Comments Inorg. Chem."},{"issue":"03","key":"10591_CR33","first-page":"29","volume":"5","author":"Y Zhang","year":"2020","unstructured":"Zhang, Y., Wei, L., Lu, L., Gan, L. & Pan, M. Adsorption-photocatalytic properties of cellulose nanocrystal supported ZnO nanocomposites. J. For. Eng. 5(03), 29\u201335 (2020).","journal-title":"J. For. Eng."},{"key":"10591_CR34","doi-asserted-by":"publisher","first-page":"292","DOI":"10.1016\/j.jobab.2021.03.003","volume":"6","author":"J Jjagwe","year":"2021","unstructured":"Jjagwe, J., Olupot, P. W., Menya, E. & Kalibbala, H. M. Synthesis and application of granular activated carbon from biomass waste materials for water treatment: A review. J. Bioresour. Bioprod. 6, 292\u2013322 (2021).","journal-title":"J. Bioresour. Bioprod."},{"key":"10591_CR35","first-page":"94","volume":"50","author":"Z Cheng","year":"2020","unstructured":"Cheng, Z., Meng, J. & Wang, X. Preparation of wood-based filter loaded with Ag nanoparticles and its catalytic degradation performance on organic dye. J. For. Eng. 50, 94\u201398 (2020).","journal-title":"J. For. Eng."},{"key":"10591_CR36","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2022.02.018","author":"C Zhao","year":"2022","unstructured":"Zhao, C., Xi, M., Huo, J., He, C. & Fu, L. Computational design of BC3N2 based single atom catalyst for dramatic activation of inert CO2 and CH4 gases into CH3COOH with ultralow CH4 dissociation barrier. Chin. Chem. Lett. https:\/\/doi.org\/10.1016\/j.cclet.2022.02.018 (2022).","journal-title":"Chin. Chem. Lett."},{"key":"10591_CR37","doi-asserted-by":"publisher","first-page":"123140","DOI":"10.1016\/j.jhazmat.2020.123140","volume":"400","author":"Y Orooji","year":"2020","unstructured":"Orooji, Y., Mortazavi-Derazkola, S., Ghoreishi, S. M., Amiri, M. & Salavati-Niasari, M. Mesopourous Fe3O4@SiO2-hydroxyapatite nanocomposite: Green sonochemical synthesis using strawberry fruit extract as a capping agent, characterization and their application in sulfasalazine delivery and cytotoxicity. J. Hazard. Mater. 400, 123140 (2020).","journal-title":"J. Hazard. Mater."},{"key":"10591_CR38","doi-asserted-by":"publisher","first-page":"122620","DOI":"10.1016\/j.fuel.2021.122620","volume":"311","author":"Z Taherian","year":"2022","unstructured":"Taherian, Z., Shahed Gharahshiran, V., Khataee, A. & Orooji, Y. Synergistic effect of freeze-drying and promoters on the catalytic performance of Ni\/MgAl layered double hydroxide. Fuel 311, 122620 (2022).","journal-title":"Fuel"},{"issue":"3","key":"10591_CR39","doi-asserted-by":"publisher","first-page":"243","DOI":"10.1016\/j.jobab.2021.04.006","volume":"6","author":"F Dai","year":"2021","unstructured":"Dai, F. et al. Porous hafnium-containing acid\/base bifunctional catalysts for efficient upgrading of bio-derived aldehydes. J. Bioresour. Bioprod. 6(3), 243\u2013253 (2021).","journal-title":"J. Bioresour. Bioprod."},{"key":"10591_CR40","doi-asserted-by":"publisher","first-page":"128005","DOI":"10.1016\/j.chemosphere.2020.128005","volume":"263","author":"M Nasrollahzadeh","year":"2021","unstructured":"Nasrollahzadeh, M., Sajjadi, M., Iravani, S. & Varma, R.S. Carbon-based sustainable nanomaterials for water treatment: state-of-art and future perspectives. Chemosphere  263, 128005 (2021).","journal-title":"Chemosphere"},{"key":"10591_CR41","doi-asserted-by":"publisher","first-page":"8891","DOI":"10.1016\/j.inoche.2021.108891","volume":"133","author":"N Fadaee Takmil","year":"2021","unstructured":"Fadaee Takmil, N. et al. Hydrogen production by electrochemical reaction using waste zeolite boosted with titania and Au nanoparticles. Inorg. Chem. Commun. 133, 8891 (2021).","journal-title":"Inorg. Chem. Commun."},{"issue":"3","key":"10591_CR42","doi-asserted-by":"publisher","first-page":"3038","DOI":"10.1007\/s10854-020-05054-3","volume":"32","author":"P Taravati Ahmad","year":"2021","unstructured":"Taravati Ahmad, P., Jaleh, B., Khazalpour, S., Gharehbaghi, R. & Varma, R. S. Electrochemical fabrication of rGO\/PANI-Au-\u03b3MnO2 nanocomposites as supercapacitor electrode materials. J. Mater. Sci. Mater. Electron. 32(3), 3038\u20133053 (2021).","journal-title":"J. Mater. Sci. Mater. Electron."},{"key":"10591_CR43","doi-asserted-by":"publisher","first-page":"16","DOI":"10.1016\/j.cej.2013.02.009","volume":"221","author":"J Feng","year":"2013","unstructured":"Feng, J. et al. CuFe2O4 magnetic nanoparticles: A simple and efficient catalyst for the reduction of nitrophenol. Chem. Eng. J. 221, 16\u201324 (2013).","journal-title":"Chem. Eng. J."},{"key":"10591_CR44","first-page":"1","volume":"16","author":"D Astruc","year":"2008","unstructured":"Astruc, D. Transition-metal nanoparticles in catalysis: from historical background to the state-of-the art. Nanoparticles Catal. 16, 1\u201348 (2008).","journal-title":"Nanoparticles Catal."},{"issue":"4","key":"10591_CR45","doi-asserted-by":"publisher","first-page":"256","DOI":"10.1016\/j.jobab.2020.10.004","volume":"5","author":"Su Mingxue","year":"2020","unstructured":"Mingxue, Su., Li, W., Ma, Q. & Zhu, B. Production of jet fuel intermediates from biomass platform compounds via aldol condensation reaction over iron-modified MCM-41 Lewis acid zeolite. J. Bioresour. Bioprod. 5(4), 256\u2013265 (2020).","journal-title":"J. Bioresour. Bioprod."},{"key":"10591_CR46","doi-asserted-by":"publisher","first-page":"258","DOI":"10.1016\/j.cej.2011.05.103","volume":"172","author":"T Shahwan","year":"2011","unstructured":"Shahwan, T. et al. Green synthesis of iron nanoparticles and their application as a Fenton-like catalyst for the degradation of aqueous cationic and anionic dyes. Chem. Eng. J. 172, 258\u2013266 (2011).","journal-title":"Chem. Eng. J."},{"key":"10591_CR47","doi-asserted-by":"publisher","first-page":"6353","DOI":"10.1016\/j.carbpol.2020.116353","volume":"241","author":"M Nasrollahzadeh","year":"2020","unstructured":"Nasrollahzadeh, M., Shafiei, N., Nezafat, Z., Bidgoli, N. S. S. & Soleimani, F. Recent progresses in the application of cellulose, starch, alginate, gum, pectin, chitin and chitosan based (nano) catalysts in sustainable and selective oxidation reactions: A review. Carbohydr. Polym. 241, 6353 (2020).","journal-title":"Carbohydr. Polym."},{"key":"10591_CR48","doi-asserted-by":"publisher","first-page":"111788","DOI":"10.1016\/j.mcat.2021.111788","volume":"513","author":"M Nasrollahzadeh","year":"2021","unstructured":"Nasrollahzadeh, M., Nezafat, Z., Bidgoli, N. S. S. & Shafiei, N. Use of tetrazoles in catalysis and energetic applications: Recent developments. Mol. Catal. 513, 111788 (2021).","journal-title":"Mol. Catal."},{"key":"10591_CR49","doi-asserted-by":"publisher","first-page":"39","DOI":"10.1016\/j.jcat.2020.04.013","volume":"387","author":"G Gao","year":"2020","unstructured":"Gao, G., Di, J.-Q., Zhang, H.-Y., Mo, L.-P. & Zhang, Z.-H. A magnetic metal organic framework material as a highly efficient and recyclable catalyst for synthesis of cyclohexenone derivatives. J. Catal. 387, 39\u201346 (2020).","journal-title":"J. Catal."},{"key":"10591_CR50","doi-asserted-by":"publisher","first-page":"39","DOI":"10.1016\/j.catcom.2016.09.028","volume":"88","author":"M Zhang","year":"2017","unstructured":"Zhang, M., Liu, Y.-H., Shang, Z.-R., Hu, H.-C. & Zhang, Z.-H. Supported molybdenum on graphene oxide\/Fe3O4: An efficient, magnetically separable catalyst for one-pot construction of spiro-oxindole dihydropyridines in deep eutectic solvent under microwave irradiation. Catal. Commun. 88, 39\u201344 (2017).","journal-title":"Catal. Commun."},{"key":"10591_CR51","doi-asserted-by":"publisher","first-page":"134730","DOI":"10.1016\/j.cej.2022.134730","volume":"434","author":"R Keyikoglu","year":"2022","unstructured":"Keyikoglu, R., Khataee, A., Lin, H. & Orooji, Y. Vanadium(V)-doped ZnFe LDH for enhanced sonocatalytic degradation of pymetrozine. Chem. Eng. J. 434, 134730 (2022).","journal-title":"Chem. Eng. J."},{"key":"10591_CR52","doi-asserted-by":"publisher","first-page":"589","DOI":"10.2147\/IJN.S338897","volume":"17","author":"SR Obireddy","year":"2022","unstructured":"Obireddy, S. R. & Lai, W.-F. ROS-generating amine-functionalized magnetic nanoparticles coupled with carboxymethyl chitosan for pH-responsive release of doxorubicin. Int. J. Nanomed. 17, 589\u2013601 (2022).","journal-title":"Int. J. Nanomed."},{"issue":"1","key":"10591_CR53","doi-asserted-by":"publisher","first-page":"1562","DOI":"10.1080\/10717544.2021.1955043","volume":"28","author":"SR Obireddy","year":"2021","unstructured":"Obireddy, S. R. & Lai, W. Preparation and characterization of 2-hydroxyethyl starch microparticles for co-delivery of multiple bioactive agents. Drug Deliv. 28(1), 1562\u20131568 (2021).","journal-title":"Drug Deliv."},{"key":"10591_CR54","doi-asserted-by":"publisher","first-page":"125589","DOI":"10.1016\/j.foodchem.2019.125589","volume":"306","author":"Y Yan","year":"2020","unstructured":"Yan, Y., Feng, L., Shi, M., Cui, C. & Liu, Y. Effect of plasma-activated water on the structure and in vitro digestibility of waxy and normal maize starches during heat-moisture treatment. Food Chem. 306, 125589 (2020).","journal-title":"Food Chem."},{"key":"10591_CR55","doi-asserted-by":"publisher","first-page":"130579","DOI":"10.1016\/j.foodchem.2021.130579","volume":"366","author":"X Li","year":"2022","unstructured":"Li, X. et al. Effect of micro- and nano-starch on the gel properties, microstructure and water mobility of myofibrillar protein from grass carp. Food Chem. 366, 130579 (2022).","journal-title":"Food Chem."},{"issue":"1","key":"10591_CR56","doi-asserted-by":"publisher","first-page":"77","DOI":"10.1016\/j.ajps.2020.05.003","volume":"16","author":"W Lai","year":"2021","unstructured":"Lai, W., Huang, E. & Lui, K. Alginate-based complex fibers with the Janus morphology for controlled release of co-delivered drugs. Asian J. Pharm. Sci. 16(1), 77\u201385 (2021).","journal-title":"Asian J. Pharm. Sci."},{"key":"10591_CR57","doi-asserted-by":"publisher","DOI":"10.1007\/s13738-021-02405-7","author":"M Nasrollahzadeh","year":"2021","unstructured":"Nasrollahzadeh, M. & Shafiei, N. Efficient synthesis of novel 3-imino-2-phenylisoindolin-1-one derivatives under ultrasound irradiation. J. Iran. Chem. Soc. https:\/\/doi.org\/10.1007\/s13738-021-02405-7 (2021).","journal-title":"J. Iran. Chem. Soc."}],"container-title":["Scientific Reports"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-10591-4.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-10591-4","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-10591-4.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,11,25]],"date-time":"2022-11-25T01:59:43Z","timestamp":1669341583000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-10591-4"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,25]]},"references-count":57,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2022,12]]}},"alternative-id":["10591"],"URL":"https:\/\/doi.org\/10.1038\/s41598-022-10591-4","relation":{},"ISSN":["2045-2322"],"issn-type":[{"value":"2045-2322","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,4,25]]},"assertion":[{"value":"3 January 2022","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"11 April 2022","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"25 April 2022","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"The authors declare no competing interests.","order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"6724"}}