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Keywords = phenol-ene coupling

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17 pages, 3957 KB  
Article
High-Strength, Stable, and Energy-Efficient Bacterial Nanocellulose Composite Films for Building-Integrated Photovoltaics Facade System
by Chenguang Wang, Libin Deng and Yanjie Zhou
Coatings 2025, 15(9), 1063; https://doi.org/10.3390/coatings15091063 - 10 Sep 2025
Viewed by 437
Abstract
Bacterial nanocellulose (BNC) composite films have emerged as promising candidates for sustainable building materials, yet their practical application in building-integrated photovoltaics (BIPV) facade systems is hindered by insufficient mechanical strength, poor environmental stability, and limited energy efficiency. Here, we developed bacterial nanocellulose/zinc oxide–phenolic [...] Read more.
Bacterial nanocellulose (BNC) composite films have emerged as promising candidates for sustainable building materials, yet their practical application in building-integrated photovoltaics (BIPV) facade systems is hindered by insufficient mechanical strength, poor environmental stability, and limited energy efficiency. Here, we developed bacterial nanocellulose/zinc oxide–phenolic resin (BNC/ZnO–PF) composite films with high-strength, stability, and energy efficiency for BIPV facade system through a simple strategy. Specifically, we first prepared BNC films, then in-situ grew ZnO nanoparticles on BNC films via ultrasound assistance, and finally hot-pressed the BNC/ZnO films with PF resin. The BNC/–PF composite films exhibit high mechanical strength (tensile strength of 93.8 MPa), exceptional sturdiness (wet strength of 92.3 MPa), and thermal properties, demonstrating their durability for long-term outdoor applications. Furthermore, the BNC/ZnO–PF composite films show high transparency (86.47%) and haze (82.02%) in the visible light range, enabling effective light propagation and scattering, as well as soft, uniform, and large-area light distribution. Meanwhile, a low thermal conductivity of 21.7 mW·m−1·K−1 can effectively impede the transfer of high outdoor temperatures into the room, significantly reducing the energy consumption demands of heating and cooling systems. Coupled with its ability to en-hance the photovoltaic conversion efficiency of solar cells by 12.9%, this material can serve as the core encapsulation layer for BIPV facades. While enabling build-ing-integrated photovoltaic power generation, through the synergistic effect of light management and thermal insulation, it is expected to reduce comprehensive building energy consumption, providing a new solution for building energy efficiency under carbon neutrality goals. Full article
(This article belongs to the Section Thin Films)
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12 pages, 705 KB  
Article
Scaptotrigona mexicana Propolis from Totonacapan Region: Chemical Composition, Antioxidant and Antibacterial Activities
by Blanca E. Rivero-Cruz, Maria Ema Rojas-Brandao, Adriana Correa-Benítez, Ingeborg Becker, Aurora Xolalpa-Aroche, José Delgado-Dominguez and J. Fausto Rivero-Cruz
Molecules 2025, 30(6), 1370; https://doi.org/10.3390/molecules30061370 - 19 Mar 2025
Viewed by 940
Abstract
The propolis produced by stingless bees is a complex mixture of natural sticky components mixed with soil or clay. Global research on propolis has focused on studying the biological and pharmacological properties and chemical composition of stingless bee propolis from Brazil, Indonesia, and [...] Read more.
The propolis produced by stingless bees is a complex mixture of natural sticky components mixed with soil or clay. Global research on propolis has focused on studying the biological and pharmacological properties and chemical composition of stingless bee propolis from Brazil, Indonesia, and other regions. However, studies of stingless bee propolis produced in Mexico are scarce. This study aimed to determine the chemical composition of the geopropolis of Scaptotrigona mexicana collected in the Totonacapan region and to evaluate its antioxidant and antibacterial activities. The phenolic contents of the ethanolic extract of the collected propolis ranged from 2.45 ± 0.03 mg GAE/g to 3.48 ± 0.56 mg GAE/g of dry extract. The total flavonoid content ranged from 0.69 ± 0.03 mg QE/g to 0.84 ± 0.009 mg QE/g of dry extract. The antioxidant activity of the ethanolic extracts was assessed via DPPH, ABTS, and FRAP assays. The minimum inhibitory concentration values exhibited by the ethanolic extract (>512 g/mL) for Gram-negative bacteria (Pseudomonas aerugunosa and Phorphyromonas gingivalis) were higher than those of Gram-positive bacteria. The stingless bee propolis extract showed the highest antibacterial activity against Streptococcus mutans (256 g/mL). Five known compounds, taraxeryl acetate (1), lupeol (3), cicloart-23-en-3β,25-diol (5), mangiferoic acid (6), and 5-(11’Z-heptadecenyl)-resorcinol (7), and two irresoluble mixtures of 3-O-acetyl-α-(2a) and 3-O-acetyl-β-amyrins (2b), and α- (4a) and -amyrins (4b), were identified by nuclear magnetic resonance spectroscopy and mass spectrometry. Additionally, 39 volatile compounds were identified via headspace-solid phase microextraction using the hyphenated gas chromatography coupled to mass spectrometry time-of-flight. The main volatile compounds detected include trans-α-bergamotene (8.15%), hexanal (7.17%), 2-heptanone (7.60%), and α-copaene (7.09%). Full article
(This article belongs to the Section Natural Products Chemistry)
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17 pages, 2183 KB  
Article
New Antibacterial and Antioxidant Chitin Derivatives: Ultrasonic Preparation and Biological Effects
by Anton R. Egorov, Omar M. Khubiev, Roman A. Golubev, Daria I. Semenkova, Andrey A. Nikolaev, Abel M. Maharramov, Gunay Z. Mammadova, Wanjun Liu, Alexander G. Tskhovrebov and Andreii S. Kritchenkov
Polymers 2024, 16(17), 2509; https://doi.org/10.3390/polym16172509 - 3 Sep 2024
Cited by 1 | Viewed by 1803
Abstract
This work focuses on the first use of ultrasonic phenol-ene coupling as a polymer analogous transformation. The ultrasonic reaction was introduced into chitin chemistry, resulting in the fast and convenient preparation of new water-soluble cationic chitin derivatives. Since water-soluble derivatives of fully deacetylated [...] Read more.
This work focuses on the first use of ultrasonic phenol-ene coupling as a polymer analogous transformation. The ultrasonic reaction was introduced into chitin chemistry, resulting in the fast and convenient preparation of new water-soluble cationic chitin derivatives. Since water-soluble derivatives of fully deacetylated chitin are poorly described in the literature, the synthesis of each new type of these derivatives is a significant event in polysaccharide chemistry. Polycations, or cationic polymers, are of particular interest as antibacterial agents. Consequently, the resulting polymers were tested for their antibacterial activity and toxicity. We found that the highly substituted polymer of medium molecular weight exhibited the most pronounced in vitro antibacterial effect. We prepared nanoparticles using the ionic gelation technique. The most effective in vitro antibacterial chitin-based systems were tested in vivo in rats. These tests demonstrated outstanding antibacterial effects combined with an absence of toxicity. Additionally, we found that the resulting polymers, unlike their nanoparticle counterparts, also exhibited strong antioxidant effects. In summary, we demonstrated the effectiveness of ultrasound in polymer chemistry and highlighted the importance of the sonochemical approach in the chemical modification of polysaccharides. This approach enables the synthesis of derivatives with improved physicochemical and biological properties. Full article
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16 pages, 2751 KB  
Article
Morphoanatomical, Histochemical, and Essential Oil Composition of the Plectranthus ornatus Codd. (Lamiaceae)
by Luiz Renan Ramos da Silva, Zelina Ataíde Correia, Ely Simone Cajueiro Gurgel, Olívia Ribeiro, Sebastião Gomes Silva, Oberdan Oliveira Ferreira, Eloisa Helena de Aguiar Andrade and Mozaniel Santana de Oliveira
Molecules 2023, 28(18), 6482; https://doi.org/10.3390/molecules28186482 - 7 Sep 2023
Cited by 3 | Viewed by 3005
Abstract
Plectranthus ornatus is a medicinal and aromatic plant used in traditional and alternative medicine. In this study, leaves of P. ornatus were collected in two cities of the state of Pará, “Quatipuru” and “Barcarena”, and were used with the objective of analyzing, through [...] Read more.
Plectranthus ornatus is a medicinal and aromatic plant used in traditional and alternative medicine. In this study, leaves of P. ornatus were collected in two cities of the state of Pará, “Quatipuru” and “Barcarena”, and were used with the objective of analyzing, through morphoanatomical data and histochemical and phytochemical studies of essential oil, the samples present structural differences and differences in their chemical composition. Anatomical and histochemical analyses were performed by transverse, using longitudinal sections of 8 μm to 10 μm to perform epidermal dissociation, diaphonization, and tests to identify classes of secondary metabolites. The essential oils were isolated by hydrodistillation, and the identification of the chemical composition was performed by gas chromatography coupled with mass spectrometry. The anatomical study shows that there is no difference between specimens collected in different locations, and stellate trichomes were identified. The histochemical study detected total lipids and acids, terpenes, polysaccharides, phenolic compounds, tannins, alkaloids, and calcium oxalate. The low essential oil yield may be related to the low density of secretory cells (glandular trichomes), the unidentified compounds in the highest concentration in the essential oil were in relation to the chemical composition of the essential oils, and the major compounds were α-pinene, sabinene, (E)-caryophyllene, caryophyllene oxide, and oct-1-en-3-ol. The results provide new information about the anatomy and histochemistry of P. ornatus. Full article
(This article belongs to the Special Issue Plant Secondary Metabolites in Medicinal and Aromatic Plants)
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19 pages, 4169 KB  
Article
Amphipolar, Amphiphilic 2,4-diarylpyrano[2,3-b]indoles as Turn-ON Luminophores in Acidic and Basic Media
by Tobias Wilcke, Alexandru Postole, Marcel Krüsmann, Matthias Karg and Thomas J. J. Müller
Molecules 2022, 27(7), 2354; https://doi.org/10.3390/molecules27072354 - 6 Apr 2022
Cited by 1 | Viewed by 2940
Abstract
A versatile amphiphilic pyrano[2,3-b]indole for halochromic turn-ON luminescence in acidic or basic media is accessed by an insertion-coupling-cycloisomerization and adjusting solubilizing and phenolic functionalities. While almost non-emissive in neutral solutions, treatment with acids or bases like trifluoroacetic acid (TFA) or 1,8-diazabicyclo[5.4.0]undec-7-ene [...] Read more.
A versatile amphiphilic pyrano[2,3-b]indole for halochromic turn-ON luminescence in acidic or basic media is accessed by an insertion-coupling-cycloisomerization and adjusting solubilizing and phenolic functionalities. While almost non-emissive in neutral solutions, treatment with acids or bases like trifluoroacetic acid (TFA) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) reveals distinct luminescence at wavelengths of 540 nm or 630 nm in propan-2-ol, respectively. Turn-ON emission can be detected at pH values as mild as pH = 5.31 or 8.70. Quantum yields in propan-2-ol are substantial for protonated (Φf = 0.058) and deprotonated (Φf = 0.059) species. Photometrically, pKa1 of 3.5 and pKa2 of 10.5 were determined in propan-2-ol. With lipophilic polyether sidechains and hydrophilic protonation and deprotonation sites the molecule can be regarded as amphipolar, which results in good solubility properties for different organic solvents. In aqueous media, an organic co-solvent like propan-2-ol (35%) or tetrahydrofuran (25%) is needed, and the solution can be diluted with pure water without precipitation of the compound. At higher concentrations of water, a turbid solution is formed, which indicates the formation of micellar structures or clusters. With dynamic light scattering we could show that these clusters increase in size with increasing water content. Full article
(This article belongs to the Special Issue Novel Fluorophores and Their Applications)
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16 pages, 1498 KB  
Article
Tandem Solid-Phase Extraction Columns for Simultaneous Aroma Extraction and Fractionation of Wuliangye and Other Baijiu
by Zhanglan He, Kangzhuo Yang, Zhipeng Liu, Mingzhe An, Zongwei Qiao, Dong Zhao, Jia Zheng and Michael C. Qian
Molecules 2021, 26(19), 6030; https://doi.org/10.3390/molecules26196030 - 4 Oct 2021
Cited by 6 | Viewed by 3427
Abstract
Wuliangye baijiu is one of the most famous baijiu in China, with a rich, harmonic aroma profile highly appreciated by consumers. Thousands of volatiles have been identified for the unique aroma profile. Among them, fatty acid esters have been identified as the main [...] Read more.
Wuliangye baijiu is one of the most famous baijiu in China, with a rich, harmonic aroma profile highly appreciated by consumers. Thousands of volatiles have been identified for the unique aroma profile. Among them, fatty acid esters have been identified as the main contributors to the aroma profile. In addition, many non-ester minor compounds, many of which are more polar than the esters, have been identified to contribute to the characteristic aroma unique to Wuliangye baijiu. The analysis of these minor compounds has been challenging due to the dominance of esters in the sample. Thus, it is desirable to fractionate the aroma extract into subgroups based on functional group or polarity to simplify the analysis. This study attempts a new approach to achieve simultaneous volatile extraction and fractionation using tandem LiChrolut EN and silica gel solid-phase extraction (SPE) columns. A baijiu sample (10 mL, diluted in 40 mL of water) was first passed through the LiChrolut EN (1.0 g) column. The loaded LiChrolut EN column was then dried with air and coupled with a silica gel (5.0 g) SPE column with anhydrous Na2SO4 (10.0 g) in between. The volatile compounds were eluted from the LiChrolut EN column and simultaneously fractionated on the silica gel column based on polarity. The simultaneous extraction and fractionation technique enabled the fractionations of all fatty acid esters into less polar fractions. Fatty acids, alcohols, pyrazines, furans, phenols, hydroxy esters, and other polar compounds were collected in more polar fractions. This technique was used to study the volatile compounds in Wuliangye, Moutai, and Fengjiu baijiu. In addition to fatty acid esters, many minor polar compounds, including 2,6-dimethylpyrazine, 2-ethyl-6-methylpyrazine, 2-ethyl-3,5-dimethylpyrazine, p-cresol, and 2-acetylpyrrole, were unequivocally identified in the samples. The procedure is fast and straightforward, with low solvent consumption. Full article
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20 pages, 658 KB  
Article
Atypical McMurry Cross-Coupling Reactions Leading to a New Series of Potent Antiproliferative Compounds Bearing the Key [Ferrocenyl-Ene-Phenol] Motif
by Pascal Pigeon, Meral Görmen, Konrad Kowalski, Helge Müller-Bunz, Michael J. McGlinchey, Siden Top and Gérard Jaouen
Molecules 2014, 19(7), 10350-10369; https://doi.org/10.3390/molecules190710350 - 17 Jul 2014
Cited by 21 | Viewed by 10691
Abstract
In the course of the preparation of a series of ferrocenyl derivatives of diethylstilbestrol (DES), in which one of the 4-hydroxyphenyl moieties was replaced by a ferrocenyl group, the McMurry reaction of chloropropionylferrocene with a number of mono-aryl ketones unexpectedly yielded the hydroxylated [...] Read more.
In the course of the preparation of a series of ferrocenyl derivatives of diethylstilbestrol (DES), in which one of the 4-hydroxyphenyl moieties was replaced by a ferrocenyl group, the McMurry reaction of chloropropionylferrocene with a number of mono-aryl ketones unexpectedly yielded the hydroxylated ferrocenyl DES derivatives, 5ac, in poor yields (10%–16%). These compounds showed high activity on the hormone-independent breast cancer cell line MDA-MB-231 with IC50 values ranging from 0.14 to 0.36 µM. Surprisingly, non-hydroxylated ferrocenyl DES, 4, showed only an IC50 value of 1.14 µM, illustrating the importance of the hydroxyethyl function in this promising new series. For comparison, McMurry reactions of the shorter chain analogue chloroacetylferrocene were carried out to see the difference in behaviour with mono-aryl ketones versus a diaryl ketone. The effect of changing the length of the alkyl chain adjacent to the phenolic substituent of the hydroxylated ferrocenyl DES was studied, a mechanistic rationale to account for the unexpected products is proposed, and the antiproliferative activities of all of these compounds on MDA-MB-231 cells lines were measured and compared. X-ray crystal structures of cross-coupled products and of pinacol-pinacolone rearrangements are reported. Full article
(This article belongs to the Special Issue Practical Applications of Metal Complexes)
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