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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2022 · IF 3.898

Application of functionalized magnetic silica nanoparticles for selective induction of three coumarin metastable polymorphs

Yiqing Chen,Xin Huang,Suping Ding,Yaoguang Feng,Na Wang,Hongxun Hao

The precise control of active pharmaceutical ingredient (API) crystal nucleation and polymorphism is a key consideration in pharmaceutical manufacturing. In this study, tunable nanoparticles were developed to regulate the nucleation process of coumarin . Magnetic silica nanoparticles with four different functional groups ( NH 2 , COOH, SH, NCO) were prepared and coated on the substrate for inducing the crystallization of coumarin. Confined melt crystallization and microspacing sublimation crystallization methods were used to investigate the regulation mechanism. The results indicated that three metastable forms of coumarin can be obtained as pure components based on the combined influence of crystallization methods and functionalized nanoparticles. Form II could be selectively obtained by microspacing sublimation crystallization on Fe 3 O 4 @SiO 2 SH substrates, and Form IV could be obtained by confined melt crystallization on Fe 3 O 4 @SiO 2 NCO substrates. Form III could be obtained by further heating Form IV crystals to 52 °C on Fe 3 O 4 @SiO 2 NCO substrates. Moreover, the polarized light microscopy results also indicated that the introduction of nanoparticles could also increase the stability of the metastable crystalline forms of coumarin. Finally, the diffusion and surface dynamics during nanoparticle induced crystallization were comparatively investigated and the corresponding polymorphic selectivity mechanism was proposed.

CAS / MDL: 10025-77-1
研究领域: 药学 · 材料科学 · 纳米技术 · 化学
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Analytical Methods · 2023 · IF 3.1

A rhodamine coumarin-derived fluorescence probe that selectively detects Fe3+ and measures radiation doses

Danni Qin,Yaqi Han,Hao Jiang,Liang Hu

We synthesized a fluorescence ratiometric probe by combining coumarin and rhodamine B with ethylenediamine to sense Fe3+ and measure ionizing radiation doses. The presence of Fe3+ caused rhodamine to transition from a closed helical structure to an open-ring structure. Additionally, fluorescence resonance energy transfer (FRET) occurred between coumarin and rhodamine B. As a result, the fluorescence intensity at 405 nm (I405) due to coumarin was decreased, whereas that at 585 nm (I585) derived from open-ring structure rhodamine B was increased. The ratio of I585 and I405 (I585/I405) linearly increased as the Fe3+ concentration increased. The probe sensed Fe3+ in a 0–110 μM range, with a lower limit of detection (LOD) of 0.226 μM. Inspired by Fricke dosimeters, we extended the probe to measure X-ray doses using the fluorescence methodology. The probe measured X-ray doses in a 0–30 Gy range with a lower LOD of 0.5 Gy. Additionally, the dosing capability was independent of the dosing rates. Our probe showed potential for detecting Fe3+ and measuring ionizing radiation doses.

研究领域: 分析化学 · 放射生物学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

Hydroxylation-Driven Microbial and Metabolic Reshaping: Coumarin Derivatives as Novel Prebiotics for Aging Gut Health

Qile Zhang,Zhengming Zhou,Yiu Ming Cheung,Hoi Wa Yeung,Minghui Li,Chufeng He,Xiao Yu Tian,Cheng Li,Wing Tak Wong

This study aimed to investigate the therapeutic potential of three naturally occurring coumarin derivatives─coumarin, umbelliferone, and esculetin, which exhibit distinct hydroxylation patterns in mitigating age-related gut dysbiosis through in vitro colonic fermentation models. By integrating antioxidant profiling, short-chain fatty acid (SCFA) profiling, 16S rRNA sequencing, and metabolomics, we assessed their structural specificity in modulating microbial ecology and metabolic pathways. Results demonstrated a hydroxylation-dependent hierarchy in antioxidant capacity and differential regulation of SCFA production. Coumarin partially enriched g__Turicimonas but showed limited SCFA induction, whereas umbelliferone selectively enhanced butyrate synthesis and enriched g__Bacteroides. Esculetin exhibited the broadest impact, characterized by both increased acetate and propionate levels and the concurrent enrichment of g__Ileibacterium and g__Enterococcus. Metabolomic profiling further revealed that three coumarins released antioxidant metabolites, correlating with microbiota-driven detoxification. These findings highlight hydroxylated coumarins as promising prebiotics that counter age-related dysbiosis via multitarget microbiota–metabolite modulation, providing a mechanistic basis for antiaging strategies.

CAS / MDL: 64-19-7
研究领域: 微生物学 · 营养科学 · 代谢组学 · 肠道微生物组 · 衰老研究 · 植物化学
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HETEROCYCLIC COMMUNICATIONS · 2014 ·Vol. 20 ·期 5 ·289-292 · IF 0.727

Selective fluorescence sensor for Cu2+ with a novel triazole Schiff-base derivative with coumarin units

Wei Wang,Wen-Jing Yuan,Qing-Lei Liu,Ya-Nan Lei,Shuai Qi,Yan Gao

Novel triazole Schiff-base derivative 3 bearing a coumarin unit was synthesized by the reaction of 4-formylbenzocoumarin ( 1 ) with 3,5-diphenyl-4-amino-1,2,4-triazole ( 2 ). The structure of the product was characterized by means of IR, MS, 1 H NMR, 13 C NMR, and elemental analysis. The UV-vis absorption and fluorescence emission spectra of compound 3 exhibit blue-shifted absorption and fluorescent enhancement upon chelation to cupric ion. Fluorometric titration revealed a 2:1 ligand to metal ratio in the complex and the binding constant of 4.62×10 6 m -1 .

研究领域: 分析化学 · 材料科学
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ACS Nano · 2019 · IF 13.903

Inversion of Circularly Polarized Luminescence of Nanofibrous Hydrogels through Co-assembly with Achiral Coumarin Derivatives

Fang Wang,Wei Ji,Peng Yang,Chuan-Liang Feng

Control over the handedness of circularly polarized luminescence (CPL) in supramolecular gels is of special significance in biology and optoelectronics; however, it still remains a great challenge to precisely and efficiently regulate the chirality of CPL. Herein, a chiral phenylalanine-derived hydrogelator and achiral coumarin derivatives can co-assemble into nanofibrous hydrogels with controllable chirality, and the handedness of CPL of these hydrogels can be efficiently inverted by coumarin derivatives through noncovalent interactions, which can be further tuned at will by incorporating metal ions into the co-assembly. The hydrogen bonds, coordination interactions, and steric hindrance are proved to be the crucial factors for the CPL inversion. This study provides feasible strategies to efficiently regulate the handedness of CPL through co-assembly, and these CPL materials may have potential applications in the fields of photoelectric devices, smart chiroptical materials, and biological systems.

研究领域: 材料科学 · 光学 · 生物学
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MOLECULES · 2025 ·Vol. 31 ·期 1 ·76 · IF 4.6

Solvent-Mediated Control of Twisted Intramolecular Charge Transfer in 7-(Diethylamino)coumarin-3-carboxylic Acid

Xilin Bai,Jing Xiao,Bingqi Du,Duidui Liu,Yanzhuo Wang,Shujing Shi,Jing Ge

Understanding the influence of solvent environments on the excited-state charge transfer process remains a fundamental question in molecular photophysics and photochemistry. While twisted intramolecular charge transfer (TICT) is crucial in determining fluorescence efficiency and photostability, the combined effects of solvent polarity and hydrogen bonding interactions are still elusive. Here, we employ steady-state and femtosecond transient absorption (fs-TA) spectroscopy with density functional theory (DFT) calculations to investigate the excited-state dynamics of 7-(diethylamino)coumarin-3-carboxylic acid (7-DCCA) in different solvents. Our findings reveal that in highly polar solvents with strong hydrogen-donating and hydrogen-accepting capabilities, 7-DCCA undergoes significant TICT formation, resulting in fluorescence quenching. Conversely, in environments with low polarity or weak hydrogen-bonding interactions, this transformation is largely suppressed. Quantitative correlation analysis utilizing the Kamlet–Taft and Catalán four-parameter models further elucidates the synergistic role of solvent polarity and specific hydrogen-bonding parameters in modulating the steady-state spectral behavior of 7-DCCA. This study provides microscopic insights into solvent–charge transfer interactions and establishes a general framework for enhancing the luminescence efficiency and structural robustness of organic optoelectronic materials through strategic solvent engineering.

研究领域: 光物理 · 光化学 · 物理化学 · 有机光电子材料 · 光谱学 · 分子动力学
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Polymer Chemistry · 2020 ·Vol. 11 ·期 37 ·6066-6072 · IF 5.342

A novel coumarin-chitosan fluorescent hydrogel for the selective identification of Fe2+ in aqueous systems

Shuangyu Xiong,Lian Duan,Xinjian Cheng

Some new chitosan-based fluorescent hydrogels have been successfully prepared by grafting coumarin derivatives onto chitosan via a Schiff base forming reaction or acid amine condensation reaction. It is worth noting that hydrogels synthesized by the Schiff base forming reaction can be used as a good fluorescent sensor for the selective recognition, detection and adsorption of Fe2+ ions in aqueous solution. Among them, the adsorption efficiency of 1 g of a fluorescent hydrogel to Fe2+ ions can reach 63.2 mg. In addition, after being further modified, hydrogels still retain the ability to identify and adsorb Fe2+. Therefore, this probe optimizes the synthetic route to chitosan-based fluorescent sensors and expands the practical application value of fluorescent hydrogels.

研究领域: 材料科学 · 环境科学 · 分析化学
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COLLOID AND POLYMER SCIENCE · 2013 ·Vol. 292 ·期 1 ·85-95 · IF 2.161

Photoinduced shape fixity and thermal-induced shape recovery properties based on polyvinyl alcohol bearing coumarin

Zhao Xiaohai,Dang Yun,Deng Jianguo,Zhang Junhua

In this paper, polyvinyl alcohol (PVA) bearing coumarin with different degrees of substitution (DS) are synthesized by esterifying hydroxyl of PVA with 7-carboxylmethoxycoumarin. The grafted polymer has photosensitive property and presents photocrosslinking due to the photodimerization between pendant coumarin groups, which affords PVA–coumarin sample photoinduced shape fixity properties. PVA–coumarin can be cross-linked after being illuminated under UV light of 360 nm; this provides the possibility that the sample has shape memory properties only if the cross-linking extent is suitable. The shape memory properties were induced by thermal as most shape memory polymer do. In fact, the shape fixity and recovery has strong relationship with DS, irradiation time, and thickness of sample. The effect of DS on the grafted polymer structure and properties has been studied by differential scanning calorimetry, thermogravimetric analysis, and UV spectra.

研究领域: 高分子科学 · 智能材料 · 光响应材料 · 形状记忆聚合物
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Journal of Analytical Science and Technology · 2021 ·Vol. 12 ·期 1 ·1-12 · IF 2.769

A multi-responsive coumarin–benzothiazole fluorescent probe for selective detection of biological thiols and hydrazine

Chen Kangni,Li Yanbo,Shang Jinyan,Li Heping

Biothiols play important roles in various physiological and biological processes, which closely related to many diseases. Hydrazine is widely used in the chemical industry, but it is harmful to humans and animals. Therefore, it is very important to develop a fluorescent probe that can simultaneously detect biological thiols and hydrazine. In this work, a new fluorescent probe (2E,4Z)-2-(benzo[d]thiazol-2-yl)-5-chloro-5-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)penta-2,4-dienenitrile (BCD) was synthesized by integrating coumarin and benzothiazole acetonitrile. Featured with four binding sites and different bonding mechanism between probe with biothiols and hydrazine, this probe exhibited fluorescent turn-on for distinguishing Cys, Hcy, GSH and hydrazine with 760-, 8-, 6- and 637-fold fluorescent intensity increase at 502, 479, 476 and 458 nm, respectively, through different excitation wavelengths. Research on the effect of pH on the fluorescent performance of BCD shows that the probe exhibits superior stability in a weakly alkaline to weakly acidic environment, which will facilitate the detection of biological thiols or hydrazine hydrate by BCD. Selectivity studies have shown that the probe has high specificity to biological thiols and hydrazine, which is of great significance to the application of BCD.

研究领域: 分析化学 · 生物化学
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Russian Journal of Physical Chemistry A · 2026 ·Vol. 100 ·期 7 ·1348-1359 · IF 0.7

The Dissolution Behavior and Intermolecular Interactions of Coumarin-3-carboxylic Acid in 12 Mono-solvents

Ren Chaobin,Yaofei Huang,He Zhu,Zhuo Chen,Junlei Shi,Chengxin Shen,Shun Yan,Jingya Peng,Huanxin Li

The solubility properties of coumarin-3-carboxylic acid (CCA) was studied in 12 kinds of alcohol and ester solvents at p = 100 kPa with the temperature range from 278.15 to 318.15 K. It was found that the solubility of CCA increases with the temperature raises. Among the selected solvents, methyl acetate showed the best dissolving ability for CCA, while 2-propanol showed the worst dissolving ability. The obtained data are neatly correlated with four models, including van’t Hoff, λ h , Wilson, and NRTL models, with λ h equation yielding the most accurate predicted results. The dissolving mechanism of CCA was investigated with intermolecular interaction between CCA and solvents by using the COSMO-RS model, and the results indicating that the dissolving process is affected by the intermolecular interaction, molecular polarity, and size of both solvents and CCA. The dissolution thermodynamics analysis shows that the dissolving process of CCA in the twelve solvents is spontaneous, endothermic, and enthalpy driven.

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JOURNAL OF HAZARDOUS MATERIALS · 2020 · IF 9.038

Highly sensitive determination of 4-nitrophenol with coumarin-based fluorescent molecularly imprinted poly (ionic liquid)

Hao Dai,Ziyi Deng,Yanbo Zeng,Jian Zhang,Yiwen Yang,Qinyan Ma,Wenling Hu,Longhua Guo,Lei Li,Shulin Wan,Haiying Liu

A coumarin-based fluorescent molecularly imprinted poly (ionic liquid) (FL-MIPIL) was prepared using a new coumarin-based alkenyl fluorescent ionic liquid (coumarin-FL-IL) as the functional monomer, IL [V 2 C 4 (mim) 2 ][(PF 6 ) 2 ] and ethyleneglycol dimethacrylate as the cross-linkers, and 4-NP as the template molecule. The absolute quantum yields of coumarin-FL-IL and FL-MIPIL were 7.26 % and 30.66 %, respectively. As a result of the electron transfer between coumarin-FL-IL which contains amino groups and 4-NP bearing hydroxyl groups, FL-MIPIL fluorescence was effectively quenched by 4-NP. The prepared FL-MIPIL sensor can rapidly respond to 4-NP within 60 s. The FL-MIPIL sensor had good linear response to 4-NP from 0.001–7.5 μM and low detection limit of 0.5 nM (S/N = 3). The FL-MIPIL sensor exhibited high sensitivity and good selectivity for 4-NP. The outstanding performance of FL-MIPIL could be ascribed to high fluorescence intensity of FL-MIPIL without matrixes and more interactions between FL-MIPIL and 4-NP. The FL-MIPIL sensor has successfully applied to the determination of 4-NP in lake, rain and waste water samples, river sediment, soil and urine samples.

研究领域: 分析化学 · 环境科学
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INORGANIC CHEMISTRY · 2024 · IF 4.3

Superior Circularly Polarized Luminescence Brightness Achieved with Chiral Heteroleptic Nine-Coordinate Coumarin-Based Tb3+ Complexes

Jiaxiang Liu,Wenqi Song,Huizhe Niu,Ying Lu,Haiyan Yang,Wentao Li,Yu-zhen Zhao,Zongcheng Miao

In order to facilitate the practical application of circularly polarized luminescence (CPL) active molecules, the CPL brightness (BCPL) must be optimized. We have applied a binary modular strategy to synthesize two chiral organo-Tb3+ complexes, [Tb(Coum)3(1R,2R-Ph-PyBox)] (2) and [Tb(Coum)3(1S,2S-Ph-PyBox)] (5), combining 3-acetyl-4-hydroxy-coumarin (Coum) and enantiopure 2,6-bis(4-phenyl-2-oxazolin-2-yl) pyridine (1R,2R/1S,2S-Ph-PyBox). The photophysical properties of these novel complexes have been fully characterized. The combined point-chiral induction capability of chiral bis(oxazoline) derivatives and the outstanding photophysical properties of the coumarin-derived ligand have resulted in an intense excited-state chiroptical activity (|glum| = 0.097–0.103) for both Tb3+ enantiomers, with a bright Tb3+-centered high-purity green emission (ΦPL = 74%) and enhanced antenna-centered absorption behavior (ε320 nm = 47820–47940 M–1 cm–1). A superior BCPL (1132.7–1205.8 M–1 cm–1 at 5D4 → 7F5) has been established for complexes 2 and 5. The strategy adopted in this work provides a new route to chiroptical organo-Tb3+ luminophores with outstanding comprehensive performance.

研究领域: 化学 · 材料科学 · 光学
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