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. 2024 Apr 3;14(16):10842-10857.
doi: 10.1039/d4ra00629a.

Fe3O4@SiO2 core/shell functionalized by gallic acid: a novel, robust, and water-compatible heterogeneous magnetic nanocatalyst for environmentally friendly synthesis of acridine-1,8-diones

Zahra Firoozi  1 , Dariush Khalili  1 , Ali Reza Sardarian  1
Affiliations

Fe3O4@SiO2 core/shell functionalized by gallic acid: a novel, robust, and water-compatible heterogeneous magnetic nanocatalyst for environmentally friendly synthesis of acridine-1,8-diones

Zahra Firoozi et al. RSC Adv. .

Abstract

In this study, we conveniently prepared a novel robust heterogeneous magnetic nanocatalyst using a Fe3O4@SiO2 core/shell stabilized by gallic acid. The catalyst was completely characterized by various physicochemical techniques, including infrared spectroscopy (FT-IR), X-ray diffraction (XRD), dynamic light scattering (DLS), transmission electron microscopy (TEM), field emission scanning electron microscopy (FE-SEM), thermogravimetric analysis (TGA), potentiometric titration, energy dispersive X-ray microanalysis (EDX), vibrating sample magnetometer (VSM), zeta potential analysis, and BET. The potential ability of the newly developed sulfonated nanocatalyst was then exploited in the multicomponent synthesis of acridine-1,8-dione derivatives by considering the green chemistry matrix and under mild conditions. Various aldehydes and amines were smoothly reacted with dimedone, affording the desired products in good to excellent yields. The introduction of sulfonic groups using gallic acid allowed the development of a water-compatible and highly recyclable catalytic system for reactions in an aqueous environment. The prepared catalyst can be readily magnetically separated and reused eight times without significant loss of activity. High synthetic efficiency, using a recyclable and eco-sustainable catalyst under mild conditions, and easy product isolation are salient features of this catalytic system, which makes this protocol compatible with the demands of green chemistry.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Concise procedure for the preparation of the Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs.
Fig. 1
Fig. 1. FT-IR spectra of: (a) Fe3O4, (b) Fe3O4@SiO2, (c) Fe3O4@SiO2-NH2, (d) Fe3O4@SiO2-NH-GA, and (e) Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs.
Fig. 2
Fig. 2. XRD patterns of (a) Fe3O4, (b) Fe3O4@SiO2, and (c) Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs.
Fig. 3
Fig. 3. (a) FE-SEM image, (b) TEM image, and (c) the particle distributions of Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs.
Fig. 4
Fig. 4. EDX spectrum of (a) Fe3O4@SiO2-NH2, (b) Fe3O4@SiO2-NH-GA, (c) Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs.
Fig. 5
Fig. 5. Graph of thermal gravimetric analysis of Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs.
Fig. 6
Fig. 6. (a) The VSM curves for Fe3O4 nanoparticles (⋯) and Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 (⋯) (b) the ability of the catalyst to be effectively recovered at the end of the reactions by an external magnetic field.
Fig. 7
Fig. 7. Zeta potential values vs. pH for Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs.
Fig. 8
Fig. 8. (a) Pore size distributions and (b) N2 adsorption–desorption isotherms of Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 NPs.
Fig. 9
Fig. 9. Recyclability of Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 nanocatalyst in the synthesis of acridine-1,8-dione.
Fig. 10
Fig. 10. (a) FT-IR and (b) XRD diagram of Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs after eight reaction cycles.
Fig. 11
Fig. 11. (a) FE-SEM, (b) TEM image and (c) DLS of Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs after eight reaction cycles.
Scheme 2
Scheme 2. Plausible mechanistic pathway for the construction of acridine-1,8-diones catalyzed by the Fe3O4@SiO2-NH-GA-[(CH2)4-SO3H]3 MNPs.
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