Vol.:(0123456789) 1 3 Journal of Inorganic and Organometallic Polymers and Materials https://doi.org/10.1007/s10904-019-01156-6 Preparation, and Antibacterial Activity of Chloroacetic Acid Immobilized on Chitosan Coated Iron Oxide Decorated Silver Nanoparticles as an Efcient Catalyst for the Synthesis of Hexahydroquinoline‑3‑Carboxamides Setareh Ghiassi 1  · Masoud Mokhtary 1  · Sajjad Sedaghat 2  · Hassan Kefayati 1 Received: 26 September 2017 / Accepted: 10 April 2019 © Springer Science+Business Media, LLC, part of Springer Nature 2019 Abstract Chloroacetic acid immobilized on chitosan (CS) coated iron oxide decorated by silver nanoparticles (Fe 3 O 4 @CS@Ag@ CH 2 COOH) was synthesized as a biocompatible magnetic material. The Fe 3 O 4 @CS@Ag@CH 2 COOH nanocomposite was characterized using FT-IR, XRD, SEM, EDS, and TGA instruments. The surface morphology and size of Fe 3 O 4 @CS@Ag@ CH 2 COOH nanocomposite were determined through SEM micrographs analysis. Moreover, magnetic characterization of the prepared nanocomposite was determined by VSM. The produced Fe 3 O 4 @CS@Ag and Fe 3 O 4 @CS@Ag@CH 2 COOH nanocomposites were screened for their antibacterial activity against gram-negative Escherichia coli and gram-positive Staphylococcus aureus. The results showed that the Fe 3 O 4 @CS@Ag and Fe 3 O 4 @CS@Ag@CH 2 COOH nanocomposites presented good antibacterial performance toward gram-negative Escherichia coli and gram-positive S. aureus. Furthermore, Fe 3 O 4 @CS@Ag@CH 2 COOH nanoparticles catalyzed one-pot synthesis of hexahydroquinoline-3-carboxamide derivatives by four-component reaction of arylaldehydes, dimedone, acetoacetanilide and ammonium acetate in ethanol at 70 °C. Keywords Chitosan · Nano-Fe 3 O 4  · Magnetic silver nanocomposites · Antibacterial activity · Hexahydroquinoline-3- carboxamide 1 Introduction Magnetic nanoparticles due to easy separation from the reaction mixture using an external magnetic feld have been particular attention in various felds in recent years. How- ever, unsupported nanoparticles are usually less stable, and often coagulation has been inevitable during the catalytic reactions. To produce stable nanoparticles with desirable activity, stabilization of the surface is required. Coating of nanoparticles has been performed by the addition of poly- mers or long-chain alkyl surfactants with polar functional groups that attach to the nanoparticle surface by covalent or electrostatic interactions. Alternatively, nanoparticles have been immobilized or grafted onto inorganic supports to improve their stabilization and recycling ability [1–3]. Chitosan, a partially acetylated glucosamine, which exist in the cell walls of some fungi such as the Mucorales, is a biopolymer with many signifcant biological and chemical properties [4–6]. The advantages of chitosan (CS) are not only its biodegradability, biocompatibility, non-toxicity, and antibacterial activity, but also the hydrophilicity introduced by the addition of the polar –OH and –NH 2 groups that are able to form hydrogen bonds with other polymers [7]. Due to these attractive properties, chitosan has found wide applica- tion as dye adsorbent [8], and in the areas of drug delivery [9, 10], biomedicine, food processing, and metal chelating [11–13]. Among the metal-based nanoparticles, nanosilver is of great interest because of its unique properties such as chemical stability, suitable conductivity, and antibacterial, antiviral, antifungal, and infammatory activities, which can be incorporated into composite fbers, cryogenic supercon- ducting materials, cosmetic products, electronic components and the food industry [14, 15]. Silver nanoparticles have * Masoud Mokhtary mmokhtary@iaurasht.ac.ir 1 Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran 2 Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran, Iran