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coumarin-3-carboxylic acid
LANGMUIR · 2015 · IF 4.457

Manipulating the Surface Chemistry of Quantum Dots for Sensitive Ratiometric Fluorescence Detection of Sulfur Dioxide

Huihui Li,Houjuan Zhu,Mingtai Sun,Yehan Yan,Kui Zhang,Dejian Huang,Suhua Wang

Herein, we report a novel approach to the rapid visual detection of gaseous sulfur dioxide (SO2) by manipulating the surface chemistry of 3-aminopropyltriethoxysilane (APTS)-modified quantum dots (QDs) using fluorescent coumarin-3-carboxylic acid (CCA) for specific reaction with SO2. The CCA molecules are attached to the surface amino groups of the QDs through electrostatic attraction, thus the fluorescence of CCA is greatly suppressed because of the formation of an ion-pair complex between the ATPS-modified QDs and CCA. Such an interaction is vulnerable to SO2 because SO2 can readily react with surface amino groups to form strong charge-transfer complexes and subsequently release the strongly fluorescent CCA molecules. The mechanism has been carefully verified through a series of control experiments. Upon exposure to different amounts of SO2, the fluorescent color of the nanoparticle-based sensor displays continuously changes from red to blue. Most importantly, the approach owns high selectivity for SO2 and a tolerance of interference, which enables the sensor to detect SO2 in a practical application. Using this fluorescence-based sensing method, we have achieved a visual detection limit of 6 ppb for gaseous SO2.

研究领域: 分析化学 · 环境科学
✓ 已验证 DOI PubMed 高影响因子
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

7-(Diethylamino) coumarin-3-carboxylic acid as a novel antibrowning agent: Activity and mechanism

Weiming Chai,Xia Yu,Yan Lin,Qiu-Han Bai,Yi-Feng Wu,Wen-Jing Wu,Hui-Ying Ou-Yang,Qiu-Xia Pan,Hui-Lin Shu

Browning caused by polyphenol oxidase (PPO) and microorganisms significantly impacts the nutritional quality of fruits and vegetables. This study identified 7-(Diethylamino) coumarin-3-carboxylic acid (7-DCCA) as an effective inhibitor of both PPO and bacteria. Enzyme assays revealed that 7-DCCA competitively inhibits PPO activity with an IC 50 value of 0.275 ± 0.002 mM. Fluorescence and molecular simulation methods demonstrated that 7-DCCA forms a complex with PPO through hydrogen bonding and hydrophobic interactions, altering the enzyme's structure and reducing its activity. Thermogravimetric and differential scanning calorimetry (DSC) assays showed that 7-DCCA stabilizes PPO, delaying its thermal decomposition. Antibacterial tests proved that 7-DCCA inhibits Staphylococcus aureus and Escherichia coli by disrupting cell membranes. Additionally, 7-DCCA suppressed PPO and peroxidase activities, delaying phenolic oxidation and preventing browning in fruits and vegetables. Cytotoxicity assays confirmed its safety, with over 85 % cell viability at concentrations up to 0.1 mM. Stability experiments verified that 7-DCCA had greatly light and thermal stability. This study highlighted 7-DCCA as a promising antibrowning agent with potential application in food preservation.

研究领域: 食品科学 · 生物化学 · 微生物学
✓ 已验证 DOI PubMed 高影响因子
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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
✓ 已验证 产品关联 DOI PubMed 高影响因子
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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.

✓ 已验证 DOI 高影响因子
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2021 · IF 4.098

Luminescent detection of pesticides by color changeable flexible coumarin-3-carboxylic acid/GdF3:Sm3+ composite film

Ziyu Chen,Zejia Zhao,Jiaxin Yang,Xiaoli Gao,Xu Sang,Adnan Khan,Rui Xu,Ming Feng,Lisa Liu,Qixin Liu,Feng Song

The utilization and residue of pesticides exist multifaceted non-restrictive effects on food safety and ecological protection. Exploitation of rapid and sensitive pesticide detection technology is imperative and will be helpful to better control the detriment of pesticides. Here, a novel flexible film has been prepared based on organic-inorganic composite materials (coumarin-3-carboxylic acid and GdF 3 :Sm 3+ ), which exhibits good optical performance and can well realize the timely and maneuverable detection for different pesticides. The spectra and luminescence properties of each composition in the composite have been analyzed systematically, and the coordinated fluorescence emission of Sm 3+ and coumarin-3-carboxylic acid is revealed at an excitation wavelength of 373 nm. Besides, the energy transfer mechanism is also researched by both experiment and theoretical calculation. The actual detection of different pesticides reveals differential fluorescence influence degree. Meanwhile, the flexible film still possesses sensitive recognition in the presence of micro concentration of pesticides. Results indicate that the flexible film with good optical performance can produce visual detection ability and provide a promising strategy for wider detection applications.

研究领域: 分析化学 · 环境科学 · 材料科学
✓ 已验证 DOI 高影响因子
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2022 · IF 8.025

Chitosan grafting coumarin-3-carboxylic acid fluorescent fiber with enhanced strength prepared by in-situ wet-spinning

Yongchun Zhou,Da Bao,Shengnan Sun,Chen Cheng,Sen Zhang,Minlin Qing,Miao Zhao,Jing Guo

Chitosan grafting coumarin-3-carboxylic acid (CS-g-CCA) fiber with fluorescent function and enhanced tensile strength was successfully prepared by in-situ wet-spinning. FTIR and NMR results demonstrate that CCA is successfully grafted onto the CS molecule chains. As the grafting rate increases from 4.2 to 15.8 %, the spinning solution viscosity increases from 22 to 54 Pa·s. SEM observations show that the CS and CS-g-CCA fiber surfaces and cross-sections exhibit homogeneity and smoothness. Likewise, as the drawing ratio increases from 1.0 to 1.4, 2D WAXS patterns illustrate the molecular chain oriented significantly along the drawing direction. The CS-g-CCA fiber (the grafting rate of 15.8 %) exhibits a maximum breaking strength of 1.06 cn/dtex, increasing by 20 % more than the CS fiber. Meanwhile, it has a peak fluorescence intensity of around 480 nm. In addition, the continuous preparation process simplifies the technological route and improves the preparation efficiency of CS-g-CCA fiber. As-prepared CS-g-CCA fiber with enhanced tensile strength and elevated fluorescence efficiency lays the foundation for potential application in fluorescent probes , anti-counterfeiting, and biomedicine fields.

CAS / MDL: 531-81-7
研究领域: 材料科学 · 生物医学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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TALANTA · 2019 · IF 4.916

7-(Diethylamino)coumarin-3-carboxylic acid as derivatization reagent for 405 nm laser-induced fluorescence detection: A case study for the analysis of sulfonamides by capillary electrophoresis

Chengxin Wu,Yuanyuan Sun,Yuanhang Wang,Wenzhen Duan,Jiangyue Hu,Lei Zhou,Qiaosheng Pu

Diode lasers, especially 405 nm diode laser, as excitation sources offer new opportunities for laser-induced fluorescence (LIF) detection, but the lack of available derivatization reagents limits their widespread applications. Herein, a commercial fluorescent dye , 7-(diethylamino)coumarin-3-carboxylic acid (DEAC-C) was introduced as derivatization reagent and corresponding derivatization strategy for DEAC-C labeling sulfonamides was developed for 405 nm LIF detection. After systematic optimization, three sulfonamides including hydrochlorothiazide (HCTZ), chlorothiazide (CTZ) and chlortalidone (CTD) could be efficiently labeled by DEAC-C in the presence of cyanuric chloride and triethylamine (1.5%) in acetonitrile at 50 °C for 180 min. Based on the laboratory-built capillary electrophoresis-LIF system, a robust method was then proposed for the separation of DEAC-C labeled sulfonamides by micellar electrokinetic chromatography (MEKC) using the classic borax-SDS system. Under the optimized conditions, a baseline separation of three sulfonamides was achieved within 15 min, and the detection limits were determined to be 0.24, 0.29, and 0.23 nM for HCTZ, CTZ, and CTD, respectively. Furthermore, the developed MEKC-LIF method was validated using sulfonamide standards and spiked human urine sample and successfully applied for the analysis of three sulfonamides in complex pharmaceutical and physiological samples.

研究领域: 分析化学 · 药学
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