Facile Synthesis of Curcumin and Curcuminoid-like Derivatives at Microwaves

Raduly, Florentina Monica; Rădiţoiu, Valentin; Rădiţoiu, Alina; Wagner, Luminiţa Eugenia; Amăriuţei, Viorica; Darvaru, Gabriela Ailiesei

doi:10.37358/rc.18.6.6319

Cited by 8 publications

(20 citation statements)

References 19 publications

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“…These maxima were given by the presence of the dye in the matrix, with a bathofluoric shift due to intermolecular interactions by hydrogen bonds. Pure curcumin derivatives in the polar environment of the silica matrix were characterized by the fluorescent emission peak at 545 nm for curcumin and 530 nm for the CA derivative [ 63 ]. The peak at 420 nm was given by the intermolecular interactions between the dye and the host matrix, as already presented by the authors in another paper [ 53 ].…”

Section: Resultsmentioning

confidence: 99%

“…For hybrids of M2 type, UV-Vis measurements were performed in order to evaluate the optical characteristics regarding the reflectance ( Figure 8 ) and transmittance ( Figure 9 ) of the obtained films. It can be seen that the properties of the coatings in which the two chromophores were present were similar along the visible spectrum, in the absorption range of pure dyes at 424 nm for CC and 419 nm for the CA derivative [ 63 ]. The differences between the two types of M2-CC and M2-CA coatings were mainly due to the intermolecular interactions established between the nanocomposites and the support.…”

Section: Resultsmentioning

confidence: 99%

“…An aqueous solution of acetic acid (10% by weight) was added to the reaction mixture, and the obtained suspension was filtered off and the solid product was washed with cold water then dried. The obtained product was purified by recrystallization from a mixture of ethyl-acetate: methanol = 3:2 ( v / v ) [ 63 ].…”

Section: Methodsmentioning

confidence: 99%

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Modeling the Properties of Curcumin Derivatives in Relation to the Architecture of the Siloxane Host Matrices

Raduly

Rădiţoiu

et al. 2021

Materials

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Research in the field of natural dyes has constantly focused on methods of conditioning curcumin and diversifying their fields of use. In this study, hybrid materials were obtained from modified silica structures, as host matrices, in which curcumin dyes were embedded. The influence of the silica network structure on the optical properties and the antimicrobial activity of the hybrid materials was monitored. By modifying the ratio between phenyltriethoxysilane:diphenyldimethoxysilane (PTES:DPDMES), it was possible to evaluate the influence the organosilane network modifiers had on the morphostructural characteristics of nanocomposites. The nanosols were obtained by the sol–gel method, in acid catalysis. The nanocomposites obtained were deposited as films on a glass support and showed a transmittance value (T measured at 550 nm) of around 90% and reflectance of about 11%, comparable to the properties of the uncovered support. For the coatings deposited on PET (polyethylene terephthalate) films, these properties remained at average values of T550 = 85% and R550 = 11% without significantly modifying the optical properties of the support. The sequestration of the dye in silica networks reduced the antimicrobial activity of the nanocomposites obtained, by comparison to native dyes. Tests performed on Candida albicans fungi showed good results for the two curcumin derivatives embedded in silica networks (11–18 mm) by using the spot inoculation method; in comparison, the alcoholic dye solution has a spot diameter of 20–23 mm. In addition, hybrids with the CA derivative were the most effective (halo diameter of 17–18 mm) in inhibiting the growth of Gram-positive bacteria, compared to the curcumin derivative in alcoholic solution (halo diameter of 21 mm). The results of the study showed that the presence of 20–40% by weight DPDMES in the composition of nanosols is the optimal range for obtaining hybrid films that host curcumin derivatives, with potential uses in the field of optical films or bioactive coatings.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Modeling the Properties of Curcumin Derivatives in Relation to the Architecture of the Siloxane Host Matrices

Raduly

Rădiţoiu

et al. 2021

Materials

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“…To obtain nanosols, without further purification, the following substances were used: organic silane derivatives (Figure 1) from Aldrich, Saint Louis, MO, USA, with purity ≤95%, tetraethylortosilicate, TEOS (Figure 1a), phenyltriethoxysilane, PTES (Figure 1b), 3-glycidoxypropyltriethoxysilane, GPTES (Figure 1c), dimethoxydimethylsilane, DMDMS (Figure 1d), dimethoxydiphenylsilane, DMDPS (Figure 1e), hydrochloric acid (0.1 N, HCl, Chimreactiv, Bucharest, Romania) ethanol (96%, EtOH, Chimreactiv, Bucharest, Romania), N-methylimidazole (99%, NMI, Aldrich, Saint Louis, MO, USA) and tetrahydrofuran (99%, THF, Merck, Kenilworth, NJ, USA). The dye (Figure 1f) with a structure similar to that of natural curcumin, was synthesized in the laboratory in microwaves and purified, by using an already known method [40]. The fabric used was 100% polyester, PES (Figure 1g…”

Section: Methodsmentioning

confidence: 99%

Optical Behavior of Curcuminoid Hybrid Systems as Coatings Deposited on Polyester Fibers

Raduly

Rădiţoiu

et al. 2022

Coatings

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The recent development of the “eco-friendly” current has brought to the attention of researchers natural dyes that are biodegradable, do not cause allergies and generally have anti-UV protection, and antioxidant and antibacterial properties. In this study, we aimed to obtain hybrid materials of the dye–host matrix type, by using the sol–gel process. The silica network was generated by tetraethylorthosilicates and modified with organic siloxane derivatives: phenyltriethoxysilane, 3-glycidoxypropyltriethoxysilane, dimethoxydimethylsilane and dimethoxydiphenylsilane. The nanocomposites obtained by embedding curcumin in siloxane matrices were deposited on polyester fabric and evaluated for their properties, relative to the type of organic network modifier used. Fabrics covered with curcuminoid hybrid systems provide a hydrophobic surface, have fluorescent properties and a UPF +50, and, therefore, they can be used in various fields where it is necessary for textiles to provide signaling, self-cleaning or protection properties against ultraviolet radiation. The coated textile materials have very good resistance properties after several repeated washing cycles, and maintain the original UV protection factor at high values even after washing or during rubbing tests.

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“…The curcumin dye (Figure 1) was synthesized at microwaves and purified using a method already published by our group [39]. Briefly, a mixture of boron trioxide (4 mmol), acetylacetone (8 mmol) and tributyl borate (3.2 mmol) was introduced in a porcelain capsule and was irradiated in a microwave oven at 300 W for 10 min.…”

Section: Curcumin Dyesmentioning

confidence: 99%

Influence of Organic-Modified Inorganic Matrices on the Optical Properties of Palygorskite–Curcumin-Type Hybrid Materials

et al. 2022

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Clays are very important from an economic and application point of view, as they are suitable hosts for organic compounds. In order to diversify the fields of application, they are structurally modified by physical or chemical methods with cationic species, and/or different bifunctional compounds, such as organosilanes. In this study, palygorskite was modified with (3-Aminopropyl) triethoxysilane, which was subsequently modified at the amino group by grafting an acetate residue. By using this strategy, two types of host hybrid materials were obtained on which curcumin derivatives were deposited. The composites obtained were structurally characterized and their photophysical properties were investigated in relation to the structure of the host matrices and interactions with curcumin-type visiting species. The hybrid composites have different colors (orange, yellow, pink), depending on the polarity of the inorganic matrices modulated by different organic groups grafted at the surface. Fluorescence emission in the visible range is characterized by the presence of two emission maxima, one belonging to the chromophore and the other influenced by the physical interactions between auxochromes and host matrices. These hybrid materials, compared to other composite structures, are obtained by a simple adsorption process. They are temperature stable in aggressive environments (acid/base) and render the fluorescent properties of dyes redundant, with improved luminescent performance compared to them.

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Facile Synthesis of Curcumin and Curcuminoid-like Derivatives at Microwaves

Cited by 8 publications

References 19 publications

Modeling the Properties of Curcumin Derivatives in Relation to the Architecture of the Siloxane Host Matrices

Modeling the Properties of Curcumin Derivatives in Relation to the Architecture of the Siloxane Host Matrices

Optical Behavior of Curcuminoid Hybrid Systems as Coatings Deposited on Polyester Fibers

Influence of Organic-Modified Inorganic Matrices on the Optical Properties of Palygorskite–Curcumin-Type Hybrid Materials

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