Dyes and Pigments最新文献

Recent developments in the bioimaging and chemosensing applications of rhodamine derivatives for metal ions detection: A review

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-28 DOI: 10.1016/j.dyepig.2024.112568

Alaa Shafie , Amal Adnan Ashour

Rhodamine derivatives have garnered extensive attention in recent years due to their significant sensing properties and structural adaptability, making them indispensable tools in sensing applications for the detection of different analytes. The ability to selectively interact with target species, coupled with their high sensitivity and rapid response, has positioned rhodamine derivatives as key components in the development of novel chemosensors for various applications in biomedical diagnostics, pharmaceutical analysis, and environmental monitoring. In addition, rhodamine derivatives have garnered significant interest in recent years due to their remarkable fluorescence properties and structural versatility, making them invaluable tools in visualizing cellular structures and processes. In this study, we review the advancements in rhodamine-based chemosensors for metal ion detection such as Cu²⁺, Cd²⁺, Co²⁺, Ag⁺, Mn²⁺, Cd²⁺, Cr³⁺, Fe²⁺, Ni²⁺, Hg²⁺, Pb²⁺, Zn²⁺, Fe³⁺, etc. and their applications in bioimaging, focusing on developments from 2021 to 2024. Also examines the sensing mechanisms of rhodamine derivatives toward the these metal ions. Additionally, the versatility of rhodamine derivatives in designing chemosensors for bioimaging applications of these cations in various live cells such as MCF7, HeLa, HEK293T, HepG2, L929, U-87, MIA PaCa-2, SiHa, HCT -116, A549, L6, MC3T3 and plant root tissues as well as in lampfishes, zebrafishes, drosophila, caenorhabditis elegans and adult mice are discussed.

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引用次数: 0

In search for a new lead white: Understanding the historical production processes for industrial-age lead white pigments (1740–1940)

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-28 DOI: 10.1016/j.dyepig.2024.112566

Iryn Bijker , Nina Deleu , Yvan Darcis , Koen Janssens , Geert Van der Snickt

In heritage science, lead white pigments are of great significance due to their omnipresence in historical polychrome and finishing layers. However, although lead white dominated the artist's palette from Antiquity until the early 20th century, modern production processes have remained largely unstudied. This paper explores the manufacturing methods from 1740 to 1940, as these differ fundamentally from the traditional ‘Dutch Stack Method’. Moreover, the technological breakthroughs of the industrial-age initiated an intensive search for improved production pathways, as attested by the 185 process descriptions found during this survey of historical textual sources. A thorough understanding of these innovative processes and their ensuing end-products is particularly relevant for the conservation field as recent studies demonstrated that the production method influences the resulting lead white subtype and its painting properties. Drawing on process descriptions in patents, technical manuals and treatises, a classification is proposed based on the underlying chemical methodology; the main categories are methods based on corrosion, precipitation, electrolysis and volatilisation. In addition, the real-life, commercial prevalence of these categories was assessed by studying literature and archival information on large-scale trade and industry. Surprisingly, these findings indicate that, despite the many innovative chemical pathways registered, the lion's share of lead white manufacturers across Europe and North America continued to employ the corrosion methods, which remain the most indebted to the traditional stack method. Nevertheless, a significant number of factories adopted the novel pathways (i.e. precipitation methods), even though the ensuing products were often considered as of lesser quality in contemporary literature.

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引用次数: 0

Intermolecular C–H⋯O hydrogen bond–induced H-aggregates for rapid, real-time detection of cyanide

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-27 DOI: 10.1016/j.dyepig.2024.112567

Sachin D. Padghan , Jiun-Wei Hu , Li-Ching Wang, Yin-Hsuan Hsu, Kew-Yu Chen

A specialized chemodosimeter, H1, incorporates a solid red fluorophore formed using a nearly planar dimethylaniline–indanedione conjugate, leveraging an intramolecular charge transfer (ICT) mechanism engineered for cyanide detection. Chemodosimeter H1 exhibits strong ICT-induced emission in polar organic solvents, although its fluorescence diminishes in the solid state. Compared with the J-aggregated solid red fluorophore J1, which has a similar dimethylaniline–indanedione conjugate structure, chemodosimeter H1, with an extended vinyl conjugation, displays a relatively weak and blue-shifted red emission in the solid state because of formation of H-aggregates induced by intermolecular C–H⋯O hydrogen bonds. Binding between cyanide and chemodosimeter H1 results in color and emission changes for the latter, resulting in formation of a highly twisted structure, denoted as H1–CN, which subsequently impedes ICT. Furthermore, test strips employing the H-aggregated red fluorophore H1 present a promising approach for quantitative and rapid detection of cyanide (CN⁻). These results provide a new approach to designing solid red fluorophores based on H-aggregation for CN⁻ detection.

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引用次数: 0

Fluorescent sensing for boronic acid derivatives: Design, synthesis, mechanism, application and perspective in Boron Neutron Capture Therapy (BNCT)

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-26 DOI: 10.1016/j.dyepig.2024.112561

Yuanfeng Qi , Wenwen Sun , Le Wang , Xiao Zhang , Xuetao Wu , Yingbo Li , Junfeng Wang

Boron is ubiquitous in nature, and drugs based on boronic acid and esters are now widely developed and used. Boron Neutron Capture Therapy (BNCT), with its high selectivity in targeting cancer cells while minimizing damage to healthy tissues, is currently an innovative cancer treatment technology being explored worldwide. The treatment process of BNCT primarily involves delivering targeted ¹⁰B drugs to the tumor site. After neutron irradiation, the ¹⁰B drugs will absorb neutrons and undergo nuclear transformation into ¹¹B which subsequently decays to produce ⁷Li and alpha particles, thereby damaging DNA and killing cancer cells. The concentration and location of the ¹⁰B drugs delivered to tumor cells are critical determinants of the therapeutic effect of BNCT, making the sensing of boronic acid drugs particularly important. In this review, the design and synthesis of various boronic acid sensors with different chelating ligands were discussed, as well as the applications in BNCT. Finally, we analyze the current limitations and propose future perspectives for these sensors to improve their utility in biomedical applications.

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引用次数: 0

Benzobisthiazole and rhodanine based low energy level small molecule donors for organic solar cells 基于苯并二噻唑和罗丹宁的有机太阳能电池低能级小分子供体

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-22 DOI: 10.1016/j.dyepig.2024.112564

Dong Han , Shuguang Wen , Kai Song , Jing Lv , Chunming Yang , Tao Zhuang , Aziz Saparbaev , Mingliang Sun , Xichang Bao

At present, high-performance small molecule donors for organic solar cells (OSCs) are almost entirely composed of the electron donating core benzodithiophene (BDT), which has resulted in a lack of material diversity and further improvement. In this article, we constructed an A-π-A′-π-A conjugated structure using electron withdrawing group benzobisthiazole (BBT) core and rhodanine end group, and synthesized two small molecule donors BBTSM-3 and BBTSM-4. Under the dual electron withdrawing effects of BBT and rhodanine, the HOMO energy levels of BBTSM-3 and BBTSM-4 reached extremely low levels (−5.60 eV and −5.64 eV), but still matched well with the acceptor Y6. In addition, through reasonable side chain regulation, BBTSM-3 exhibited stronger crystallinity and weaker aggregation at the same time. This provides a reference point for the use of the electron withdrawing core and the regulation of side chains among small molecule donors.

目前，用于有机太阳能电池（OSC）的高性能小分子供体几乎全部由电子供体核心苯并二噻吩（BDT）组成，这导致材料缺乏多样性和进一步改进。本文利用电子汲取基团苯并二噻唑（BBT）核心和罗丹宁末端基团构建了 A-π-A′-π-A 共轭结构，并合成了两种小分子供体 BBTSM-3 和 BBTSM-4。在BBT和罗丹宁的双重退电子作用下，BBTSM-3和BBTSM-4的HOMO能级达到了极低的水平（-5.60 eV和-5.64 eV），但仍能与受体Y6很好地匹配。此外，通过合理的侧链调节，BBTSM-3 同时表现出更强的结晶性和更弱的聚集性。这为小分子供体中电子撤回核的使用和侧链的调节提供了参考。

引用次数: 0

Fabrication of 3D TPU microfiber structures with embedded dye probes for cyanide ion sensing via charge-reversed electro jet writing 通过电荷反向电动喷射写入技术，制备内嵌染料探针的三维热塑性聚氨酯微纤维结构，用于氰化物离子传感

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-22 DOI: 10.1016/j.dyepig.2024.112563

Palanisamy Jayasudha , Ramalingam Manivannan , Jaeyu Lee , Kyung Jin Lee , Young-A Son

An extremely organized sensing system that indicates the prompt indication of the cyanide ion in water was synthesized. The design of the sensing probe comprises the phenothiazine fluorophore system as an electron donor and tetramethyl-3H-indol-1-ium as an electron acceptor unit. A notable color change in daylight and UV light was observed in the probe when it comes in contact with the solution of cyanide ion. The probe interaction with the cyanide ion results in color change from purple to colorless and these changes occurs in the probe with the disconnection in the ICT process. The detection limit (LOD) 1.3 μM (UV–visible method) and 25 nM (Fluorescence method), denotes that the probe preferentially reacts with cyanide, which is less than the tolerable level of 1.9 μM. The probe reacts with cyanide ions via nucleophilic addition reaction mechanism and it is confirmed through the ¹H NMR data. Furthermore, the HRMS value also confirms the same. For practical application of the probe a 3D structure composed of TPU microfiber containing probe molecule was fabricated by charge reversed electro jet writing (CREW) method by 3D printer has been efficiently sense cyanide ion. Also, for cyanide ion sensing probe successfully determines real resources, including cyanide containing various water samples. Besides, the developed PBI-encapsulated Polysulfone (PSF) capsule kit effectively sense cyanide ion in water. Moreover, the test strips, was also employed to detect the cyanide ion in presence of competing anions. Therefore, the synthesized probe displays an outstanding sensing ability towards the cyanide ion.

我们合成了一种非常有组织的传感系统，它能迅速显示水中的氰离子。该传感探针的设计包括作为电子供体的吩噻嗪荧光团系统和作为电子受体单元的四甲基-3H-吲哚-1-鎓。当探针与氰离子溶液接触时，在日光和紫外光下可观察到明显的颜色变化。探针与氰离子的相互作用导致颜色从紫色变为无色，这些变化是探针在信息和通信技术过程中断开连接时发生的。检测限（LOD）为 1.3 μM（紫外可见光法）和 25 nM（荧光法），表明探针优先与氰化物发生反应，低于 1.9 μM 的可容忍水平。探针通过亲核加成反应机理与氰离子反应，这一点通过 1H NMR 数据得到了证实。此外，HRMS 值也证实了这一点。为了探针的实际应用，利用三维打印机通过电荷反向电喷射写入（CREW）方法制作了含有探针分子的 TPU 超细纤维三维结构，该结构可有效感应氰化物离子。此外，氰化物离子感应探针还成功测定了实际资源，包括含氰化物的各种水样。此外，所开发的 PBI 封装聚砜（PSF）胶囊试剂盒可有效感测水中的氰离子。此外，该试纸还能在存在竞争阴离子的情况下检测氰离子。因此，合成的探针对氰离子具有出色的感应能力。

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引用次数: 0

Unravelling the intricacies of fluorescence enhancement in heptamethine cyanine dyes induced by heavy halogen atoms 揭示重卤素原子诱导七甲烷氰基染料荧光增强的复杂性

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-21 DOI: 10.1016/j.dyepig.2024.112548

Dmytro Kobzev, Olesia Kulyk, Olga Semenova, Valeriia Ananieva, Oleg Zhikol, Iryna Omelchenko, Anatoliy Tatarets

The classic heavy-atom effect refers to the photophysical phenomenon observed in fluorophores, where the interaction with heavy atoms quenches fluorescence emission. Many fluorophores containing heavy halogen atoms, such as xanthenes, BODIPYs, porphyrins, and anthracenes, adhere to this effect, while the photophysical behavior of others, e.g. halogenated heptamethine cyanine dyes, is poorly studied having contradicting results. In this study, we explored for the first time unexpected fluorescence enhancement induced by heavy halogen atoms in heptamethine dyes, contrasting the classic heavy-atom effect. To this end, a series of novel heptamethine cyanine dyes were synthesized and their photophysical properties were experimentally and theoretically investigated. Heavy halogen atoms were found to significantly affect the fluorescence behaviour of heptamethine dyes depending on the number and position of the attached halogens. Thus, the introduction of bromine and iodine atoms at the non-conjugated positions to the chromophore moieties led to an increase in the fluorescence quantum yields, which contradicts the classic principle and could be explained by heavy halogen-induced vibration restrictions. The value of halogen atom-promoted singlet oxygen generation quantum yield Φ_Δ is also not straightforward and depends on the number, position and weight of the halogen atom. The breaking of the classic heavy-atom effect in halogenated heptamethine dyes provides an effective strategy to substantially increase the fluorescence intensity of long-wavelength cyanine dyes, providing new functional advantages for fluorescence imaging, diagnostics, and photodynamic therapy, among other applications.

经典的重原子效应是指在荧光团中观察到的一种光物理现象，即与重原子的相互作用会淬灭荧光发射。许多含有重卤素原子的荧光团（如呫吨、BODIPYs、卟啉和蒽）都具有这种效应，而对其他荧光团（如卤代七甲氰染料）的光物理行为研究较少，结果相互矛盾。在本研究中，我们首次探索了七甲基染料中重卤原子诱导的意想不到的荧光增强效应，与经典的重原子效应形成鲜明对比。为此，我们合成了一系列新型七甲氧基氰基染料，并对其光物理性质进行了实验和理论研究。研究发现，重卤原子会显著影响七甲基染料的荧光特性，这取决于所附卤素的数量和位置。因此，在发色团分子的非共轭位置引入溴原子和碘原子会导致荧光量子产率增加，这与经典原理相悖，可以用重卤素引起的振动限制来解释。卤素原子促进单线态氧生成的量子产率ΦΔ的值也并不简单，它取决于卤素原子的数量、位置和重量。打破卤代七甲基染料中经典的重原子效应为大幅提高长波长氰基染料的荧光强度提供了有效策略，为荧光成像、诊断和光动力疗法等应用提供了新的功能优势。

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引用次数: 0

Synthesis and photophysical characterization of push-pull azobenzene derivatives featuring different π-bridges for photoresponsive applications 具有不同 π 桥的推挽式偶氮苯衍生物的合成与光物理特性分析，用于光致发光应用

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-20 DOI: 10.1016/j.dyepig.2024.112550

Ismi Simpang Anggia , Dini Hayati , Jongin Hong

This study presents the synthesis, development, and comprehensive evaluation of a series of novel azobenzene derivatives – DMAC, DMAF, and DMAT – engineered with push-pull configuration by varying π-bridge substituents (benzene, furan, and thiophene, respectively). The research employs a combination of computational and experimental methods, including density functional theory (DFT) and time-resolved UV–Vis absorption spectroscopy, to explore the impact of these π-bridge modifications on the electronic, photophysical, and isomerization properties of the derivatives. Interestingly, the findings suggest that the π-bridge structure significantly influences the charge transfer characteristics, with DMAC exhibiting the most effective charge transfer and the highest photoisomerization efficiency. Time-resolved UV–Vis absorption spectroscopy demonstrates that all derivatives exhibit rapid initial E-to-Z isomerization upon light irradiation, followed by a slower approach to the photostationary state (PSS). Thermal Z-to-E isomerization kinetics are consistent with the activation energy barriers predicted by potential energy surface (PES) scans, with DMAC showing the slowest reversion due to its highest activation energy. This study contributes valuable insights into the structural influences on the photochemical dynamics of azobenzene derivatives, with implications for their applications in photoresponsive technologies.

本研究介绍了一系列新型偶氮苯衍生物--DMAC、DMAF 和 DMAT--的合成、开发和综合评估，这些衍生物通过改变π桥取代基（分别为苯、呋喃和噻吩）设计成推拉构型。研究采用了计算和实验相结合的方法，包括密度泛函理论（DFT）和时间分辨紫外可见吸收光谱，以探索这些π桥修饰对衍生物的电子、光物理和异构化特性的影响。有趣的是，研究结果表明，π桥结构对电荷转移特性有显著影响，其中 DMAC 表现出最有效的电荷转移和最高的光异构化效率。时间分辨紫外-可见吸收光谱表明，所有衍生物在光照射下都表现出从 E 到 Z 的快速初始异构化，随后缓慢进入光静止态（PSS）。热Z-E异构化动力学与势能面（PES）扫描预测的活化能势垒一致，其中DMAC因其活化能最高而表现出最慢的还原。这项研究有助于深入了解偶氮苯衍生物的结构对光化学动力学的影响，对它们在光致发光技术中的应用具有重要意义。

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引用次数: 0

Rational integration of fluorogenic and quenching activity of dopamine for reversed ratiometric and semi-quantitative visual detection of tyramine 合理整合多巴胺的荧光活性和淬灭活性，实现酪胺的反向比率测量和半定量视觉检测

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-20 DOI: 10.1016/j.dyepig.2024.112559

Mingyue You , Lingling Liu , Yuanmin Gong , Rui Shi , Long Yuan , Jiaqi Chen , Kai Zhou , Xueping Tao , Gaoyi Yi , Zhining Xia , Qifeng Fu

A facile and efficient reversed ratiometric fluorescence (RF) method has been developed for the sensitive and accurate detection of tyramine (Tyr), an essential marker for food spoilage in fermented or aged foods. This method utilizes an “activation-quenching integration” strategy involving the fluorogenic reactivity and quenching capacity of dopamine (DA), the tyrosinase (TYR) catalyzed products of Tyr. Under alkaline conditions, DA reacts with resorcinol to form azamonardine, exhibiting strong blue emission. Additionally, DA is oxidized to o-dopaquinone by TYR, which quenches the red fluorescence of CdTe quantum dots (QDs). Under optimized conditions, a Tyr-specific RF sensor was established, featuring a linear detection range from 0.1 to 6 mg/mL and a detection limit of 8.50 × 10⁻³ mg/L. The fabricated reversed RF sensing system was successfully applied for quantitative analysis of Tyr in real samples and semi-quantitative visual detection of Tyr in fermented food samples upon integration with a pseudo-color-assisted approach.

我们开发了一种简便高效的反向比率荧光（RF）方法，用于灵敏准确地检测发酵或陈化食品中的酪胺（Tyr），酪胺是食品腐败的一个重要标志。该方法采用 "活化-淬灭一体化 "策略，涉及酪氨酸的酪氨酸酶催化产物多巴胺（DA）的荧光反应性和淬灭能力。在碱性条件下，DA 与间苯二酚反应生成氮杂蒙那定，发出强烈的蓝色光。此外，DA 还会被 TYR 氧化成邻多巴醌，从而淬灭碲化镉量子点（QD）的红色荧光。在优化条件下，建立了酪氨酸特异性射频传感器，其线性检测范围为 0.1 至 6 mg/mL，检测限为 8.50 × 10-3 mg/L。制备的反向射频传感系统成功地应用于实际样品中 Tyr 的定量分析，以及与伪彩色辅助方法相结合后发酵食品样品中 Tyr 的半定量视觉检测。

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引用次数: 0

Selective and sensitive detection of glutathione with a novel fluorescein-based probe in fully aqueous media and its application in food samples 利用新型荧光素探针在全水介质中选择性灵敏检测谷胱甘肽及其在食品样品中的应用

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments

Pub Date : 2024-11-20 DOI: 10.1016/j.dyepig.2024.112551

Garen Suna , Sema Topal , Erman Karakuş

We devised a novel fluorescent probe, FL–T, bearing fluorescein and thienyl acrylic acid moiety, which was designed and synthesised to detect glutathione (GSH). Utilising micelle-catalysed cyclisation/elimination reaction, FL–T demonstrated exceptional sensitivity and operability in a fully aqueous solution, with a low limit of detection (LOD = 41.2 nM), and superior selectivity over cysteine (Cys), homocysteine (Hcy), H₂S and other analytes. Furthermore, FL–T successfully detected GSH in fruit and vegetable samples. These findings suggest that FL–T is a promising tool for detecting GSH in various environments.

我们设计并合成了一种新型荧光探针 FL-T，它含有荧光素和噻吩丙烯酸分子，用于检测谷胱甘肽（GSH）。利用胶束催化的环化/消除反应，FL-T 在全水溶液中表现出极高的灵敏度和可操作性，检测限低（LOD = 41.2 nM），对半胱氨酸（Cys）、同型半胱氨酸（Hcy）、H2S 和其他分析物具有极佳的选择性。此外，FL-T 还能成功检测水果和蔬菜样品中的 GSH。这些研究结果表明，FL-T 是检测各种环境中 GSH 的理想工具。

引用次数: 0