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5′-Substituted Indoline Spiropyrans: Synthesis and Applications 5 ' -取代吲哚类螺吡喃的合成与应用
Pub Date : 2023-06-05 DOI: 10.3390/colorants2020017
A. Khodonov, N. Belikov, A. Lukin, A. Laptev, V. A. Barachevsky, S. Varfolomeev, O. Demina
Methods for preparation of 5′-substituted spiropyrans, their chemical properties, and the effects of various factors on the relative stabilities of the spiropyrans and their isomeric merocyanine forms are examined, reviewed, and discussed.
对5′取代螺吡喃的制备方法、化学性质以及各种因素对螺吡喃及其异构体merocyanine形式的相对稳定性的影响进行了考察、评述和讨论。
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引用次数: 0
Diphenyl-Furanones and Diphenyl-Oxopyrrole Derivatives: From Analytical Reagents for Amino Groups to New Fluorochromes for Cytochemical Staining of Chromatin DNA and Chromosomes: Proposal for Intercalative Binding and Fluorescence Mechanism 二苯基呋喃酮和二苯基氧吡咯衍生物:从氨基分析试剂到用于染色质DNA和染色体细胞化学染色的新型荧光染料:插层结合和荧光机制的建议
Pub Date : 2023-05-15 DOI: 10.3390/colorants2020016
J. Stockert, Silvina A. Romero, M. N. FELIX-POZZI, A. Blázquez-Castro
Diaryl-furanones are specific analytical reagents for the biochemical detection of primary amines by fluorescence techniques. Well-known reagents are fluorescamine (Fluram) and 2-methoxy-2,4-diphenyl-3(2H)-furanone (MDPF), yielding fluorescent products with λem at 480–490 nm. Although the reaction products claim to be pyrrolinones, recent studies show that they are really 3-oxopyrrole (pyrrolone) derivatives. Both reagents have been used for the cytochemical demonstration of primary amines. In this work, we have applied the fluorescent products of MDPF with amines (n-butylamine, BA; glucosamine, GA; and spermine, Sp), which showed interesting fluorescence reactions with chromatin DNA. 2,4-diphenyl-3-oxopyrrole products (diPOPy) can be easily synthesized according to well-known procedures, by mixing solutions of MDPF in acetone with water at pH 9 containing the amino compounds. DiPOPy derivatives of BA, GA, and Sp were used for spectroscopic, microscopic, and molecular modeling studies, showing a bright and selective blue–green fluorescence on DNA substrates, mainly chromatin, kinetoplast DNA, and stretched chromatin fibers. The cationic diPOPy fluorophore is planar, with a high partial positive charge in the N atom, and suitable for intercalative binding to DNA. A mechanism of fluorescamine fluorescence due to an inner-salt isomeric form is proposed, and an astonishing correlation between adenine–thymine-rich centromeric heterochromatin in mouse metaphase chromosomes after reaction of the fluorescamine reagent with protein amino groups is also discussed.
二芳基呋喃酮是荧光技术用于伯胺生化检测的特异分析试剂。荧光胺(Fluram)和2-甲氧基-2,4-二苯基-3(2H)-呋喃酮(mmdf)是著名的荧光试剂,在480-490 nm范围内产生λem的荧光产物。虽然反应产物声称是吡咯啉酮,但最近的研究表明,它们实际上是3-氧吡咯(吡咯酮)衍生物。这两种试剂已用于伯胺的细胞化学演示。在本工作中,我们将mpf的荧光产物与胺(正丁胺,BA;葡萄糖胺,遗传算法;和精胺(Sp),它们与染色质DNA表现出有趣的荧光反应。2,4-二苯基-3-氧吡咯产品(diPOPy)可以很容易地合成,根据众所周知的程序,混合的MDPF溶液在丙酮和水在pH 9含氨基化合物。BA、GA和Sp的双聚y衍生物被用于光谱、微观和分子建模研究,在DNA底物上显示出明亮的选择性蓝绿色荧光,主要是染色质、着丝体DNA和拉伸的染色质纤维。阳离子双聚荧光团是平面的,在N原子上具有高的部分正电荷,适合与DNA插入结合。本文提出了荧光胺因盐内异构体形式而产生荧光的机制,并讨论了荧光胺试剂与蛋白质氨基反应后小鼠中期染色体中富含腺嘌呤-胸腺嘧啶的着丝点异染色质之间的惊人相关性。
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引用次数: 0
Dragon Fruit (Hylocereus polyrhizus): A Green Colorant for Cotton Fabric 火龙果(Hylocereus polyrhizus):棉织物绿色着色剂
Pub Date : 2023-05-11 DOI: 10.3390/colorants2020015
Md. Himel Mahmud, Md. Tanvir Raihan, Md. Tarik Zaman Shakhik, Fauzia Tasnim Khan, M. T. Islam
The textile industry has been exploring sustainable chemicals and natural alternatives to replace harmful and carcinogenic substances used in different stages of textile production for dyeing textiles. Natural dyes are gaining popularity, as they are environmentally friendly and less harmful. Betacyanin, a type of pigment obtained from red pitahaya, commonly known as red dragon fruit (Hylocereus polyrhizus), has peels that are available as agricultural waste and can be used to meet the demand for natural dye production. This study aimed to explore and utilize dragon fruit’s peel as a natural colorant for dyeing 100% cotton knit fabric (scoured and bleached single jersey plain knit) of 170 g/m2, which could transform a low-value material into a valuable product. However, cotton’s phenolic nature and oxidation process result in negative charges on its surface, making natural dyeing challenging. Cationization with cationic agents (ForCat NCH, a mixture of cationic polyamine and 1,3,dichlori-2-propanol) and mordanting (potassium alum or potassium aluminum sulfate) were carried to improve dye exhaustion and enhance colorfastness properties. Spectrophotometer 800 was used to measure color strength (K/S), and several fastness tests, including wash, perspiration, and rubbing were conducted to assess the final product’s performance. The process parameters, such as temperatures, times, pH levels, and dye concentrations were varied to understand better the optimum conditions.
纺织工业一直在探索可持续化学品和天然替代品,以取代在纺织生产的不同阶段用于染色纺织品的有害和致癌物质。天然染料越来越受欢迎,因为它们对环境友好,危害小。Betacyanin是一种从红火龙果(俗称红火龙果)中提取的色素,其果皮可作为农业废物使用,可用于满足天然染料生产的需求。本研究旨在探索和利用火龙果皮作为天然着色剂,对170 g/m2的100%纯棉针织物(水洗平纹针织单品)进行染色,将低价值材料转化为高价值产品。然而,棉花的酚性和氧化过程导致其表面带负电荷,使自然染色具有挑战性。用阳离子剂(ForCat NCH,阳离子多胺与1,3,二氯-2-丙醇的混合物)和媒染剂(明矾钾或硫酸铝钾)进行阳离子化,以改善染料的耗尽性和提高色牢度。使用分光光度计800测量颜色强度(K/S),并进行若干牢度测试,包括洗涤、排汗和摩擦,以评估最终产品的性能。改变工艺参数,如温度、时间、pH值和染料浓度,以更好地了解最佳条件。
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引用次数: 1
Effective Removal of Methyl Orange Dyes Using an Adsorbent Prepared from Porous Starch Aerogel and Organoclay 多孔淀粉气凝胶和有机粘土制备的吸附剂对甲基橙染料的有效去除
Pub Date : 2023-05-01 DOI: 10.3390/colorants2020014
Rihem Jemai, M. Djebbi, S. Boubakri, H. B. Rhaiem, A. Ben Haj Amara
Intending to provide efficient and compact wastewater remediation, the present work is exploiting and introducing a novel composite prepared from porous starch aerogel (PSA) and organically modified Ca-montmorillonite (OMMT) for the removal of dyes from aqueous samples. First, potato starch components were used as a hydrolysis precursor to obtain PSA. The organoclay samples were prepared by co-intercalation of octadecylamine (ODA) into Ca-MMT using a low-temperature melting procedure. Composites with different starch-to-organoclay ratios of 10:1, 1:1, and 1:10 were then prepared by a blending process in distilled water and used for methyl orange (MO) uptake. The removal of methyl orange dyes increased with the amount of organoclay in the PSA matrix. Characterization revealed that organoclay synergy improved the PSA surface chemistry, while an important improvement in textural properties and thermal stability was also observed. The composite’s efficiency was demonstrated by high removal capabilities towards MO in most experimental runs, with a maximum adsorption capacity beyond 344.7 mg/g. The fitting result showed that MO adsorption follows a monolayer adsorption model, and chemisorption was the rate-controlling step. Nonetheless, this study proved the great potential of PSA/OMMT in dyeing wastewater treatment. Furthermore, starch modification is proven as an effective approach to enhancing the performance of starch-derived adsorbents.
为了提供高效和紧凑的废水修复,本工作开发和介绍了一种由多孔淀粉气凝胶(PSA)和有机改性钙蒙脱土(OMMT)制备的新型复合材料,用于去除水中样品中的染料。首先,马铃薯淀粉组分作为水解前驱体得到PSA。采用低温熔融法将十八胺(ODA)共插到Ca-MMT中制备有机粘土样品。然后在蒸馏水中混合制备了淀粉与有机粘土比例分别为10:1、1:1和1:10的复合材料,用于甲基橙(MO)的吸收。甲基橙染料的去除率随着有机粘土在PSA基质中的用量的增加而增加。表征表明,有机粘土协同作用改善了PSA的表面化学性质,同时也观察到其结构性能和热稳定性的重要改善。在大多数实验中,该复合材料对MO具有较高的去除能力,最大吸附量超过344.7 mg/g。拟合结果表明,MO的吸附服从单层吸附模型,化学吸附是控制速率的步骤。尽管如此,本研究证明了PSA/OMMT在印染废水处理中的巨大潜力。此外,淀粉改性被证明是提高淀粉类吸附剂性能的有效途径。
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引用次数: 1
Is There an International Klein Pink? 有国际通用的克莱因粉吗?
Pub Date : 2023-04-25 DOI: 10.3390/colorants2020013
Abed Haddad, C. Rogge
Yves Klein (1928–1962) is best known for his intensely blue monochromatic works made with International Klein Blue (IKB), a synthetic ultramarine blue pigment bound in a poly(vinyl acetate) binder. However, he also made monochromes in other colors, including red and pink, the pigments of which have never been elucidated. Analysis of one sculpture, three paintings, and one screenprint by micro-Fourier transform infrared spectroscopy (µ-FTIR), Raman and surface-enhanced Raman (SERS) spectroscopies, portable X-ray fluorescence spectroscopy (p-XRF), and scanning electron microscopy (SEM) coupled with energy dispersive X-ray spectrometry (EDX), revealed that Klein used, knowingly or unknowingly, a variety of pink and red pigments, including Para Red, rhodamine 6G, rhodamine B, eosin Y, and alizarin lakes. The unexpected variety of pigments contrasts with his use of a single blue pigment and suggests he may not have held a singular vision of what constituted an iconic red or pink color.
伊夫·克莱因(1928-1962)最著名的作品是用国际克莱因蓝(IKB)制作的强烈的蓝色单色作品,这是一种合成的深蓝色颜料,结合在聚(醋酸乙烯)粘合剂中。然而,他也制作了其他颜色的单色,包括红色和粉红色,这些颜色的颜料从未被阐明。通过微傅里叶变换红外光谱(µ-FTIR)、拉曼光谱和表面增强拉曼光谱(SERS)、便携式x射线荧光光谱(p-XRF)、扫描电子显微镜(SEM)以及能量色散x射线光谱(EDX)对一件雕塑、三幅画和一幅丝网印刷进行分析,发现Klein有意或无意地使用了多种粉红色和红色颜料,包括对红、罗丹明6G、罗丹明B、伊红Y和茜素湖。出人意料的颜料种类与他使用的单一蓝色颜料形成鲜明对比,表明他可能对构成标志性的红色或粉红色没有单一的看法。
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引用次数: 0
Long-Alkyl Chain Functionalized Imidazo[1,5-a]pyridine Derivatives as Blue Emissive Dyes 长烷基链功能化咪唑[1,5-a]吡啶衍生物作为蓝色染料
Pub Date : 2023-04-10 DOI: 10.3390/colorants2020012
Nadia Barbero and Simone, S. Galliano, Gioele Colombo, Anita Cinco, G. Ardizzoia, S. Brenna
A series of boron difluoride compounds with 2-(imidazo[1,5-a]pyridin-3-yl)phenols bearing alkylic chains at the 1-position has been synthesized and characterized both with 1H and 13C NMR and infrared spectroscopy. This series of compounds displayed blue emission in solution and in thin polymeric films, with interesting features like large Stokes shifts and good fluorescence quantum yields. Time-Dependent Density Functional Theory (TD-DFT) calculations allowed for the identification of the main electronic transitions as intra ligand transitions (1ILT), as corroborated by the Natural Transition Orbitals (NTOs) shapes.
合成了一系列1位含2-(咪唑[1,5- A]吡啶-3-基)苯酚的二氟化硼化合物,并用1H、13C NMR和红外光谱对其进行了表征。这一系列化合物在溶液和聚合物薄膜中都显示出蓝色发射,具有有趣的特征,如大的斯托克斯位移和良好的荧光量子产率。时间依赖密度泛函理论(TD-DFT)计算允许识别主要电子跃迁为配体内跃迁(1ILT),并由自然跃迁轨道(NTOs)形状证实。
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引用次数: 2
N-Annulated Perylene Diimide Non-Fullerene Acceptors for Organic Photovoltaics 有机光伏用n-环苝二亚胺非富勒烯受体
Pub Date : 2023-03-21 DOI: 10.3390/colorants2010011
Mahmoud E. Farahat, G. Welch
This work covers the development of non-fullerene acceptors for use in organic photovoltaics built using the N-annulated perylene diimide dye. The classic perylene diimide dye has been extensively used to construct non-fullerene acceptors, leading to device power conversion efficiencies of over 10%. Strong visible light absorption and deep frontier molecular energy levels have made such materials (both molecular and polymeric) near ideal for pairing with narrow-gap conjugated polymers in bulk-heterojunction active layers. The N-annulation of the dye provides an extra site for side-chain engineering and alters the electronic structure of the polycyclic aromatic core. In addition, N-annulation allows for selective bromination of the perylene core, leading to building blocks that are useful for the construction of large molecular frameworks using the atom-economical direct heteroarylation cross-coupling method. Herein, we detail a series of molecules developed by our team that are based on the N-annulated perylene diimide in the form of dimers with different cores (both electron-rich and electron-deficient); dimers with varied side chains; tetramers with varying geometries; and large, asymmetric molecules with internal energy cascades. The use of these molecules as non-fullerene acceptors in organic photovoltaic devices (binary and ternary blends, outdoor and indoor light applications, and spin-coated vs. slot-die-coated photoactive layers) is presented.
这项工作涵盖了非富勒烯受体的发展,用于使用n环苝二亚胺染料构建的有机光伏发电。经典的苝二亚胺染料已被广泛用于构建非富勒烯受体,导致器件功率转换效率超过10%。强可见光吸收和深前沿分子能级使得这种材料(分子和聚合物)在体异质结活性层中与窄间隙共轭聚合物配对接近理想。染料的n环化为侧链工程提供了一个额外的位置,并改变了多环芳烃核的电子结构。此外,n -环化允许对苝核心进行选择性溴化,从而产生可用于使用原子经济型直接杂芳基交叉偶联方法构建大分子框架的构建块。在这里,我们详细介绍了由我们的团队开发的一系列分子,这些分子基于具有不同核(富电子和缺电子)的二聚体形式的n环苝二酰亚胺;具有不同侧链的二聚体;具有不同几何形状的四聚体;还有内能级联的大型不对称分子。介绍了这些分子作为非富勒烯受体在有机光伏器件(二元和三元共混物,室外和室内光应用,以及自旋涂层与槽模涂层光活性层)中的应用。
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引用次数: 1
Acknowledgment to the Reviewers of Colorants in 2022 向2022年着色剂审稿人致谢
Pub Date : 2023-03-17 DOI: 10.3390/colorants2010009
High-quality academic publishing is built on rigorous peer review [...]
高质量的学术出版建立在严格的同行评审的基础上[…]
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引用次数: 0
Alternative Sources of Natural Photosensitizers: Role of Algae in Dye-Sensitized Solar Cell 天然光敏剂的替代来源:藻类在染料敏化太阳能电池中的作用
Pub Date : 2023-03-17 DOI: 10.3390/colorants2010010
E. Armendáriz-Mireles, C. Calles-Arriaga, W. Pech-Rodríguez, Adalberto Castillo-Robles, E. Rocha-Rangel
In this paper, the potential of marine algae to act as sensitizers is systematically studied and presented. We aim to find a feasible financial strategy to enhance the global efficiency of dye-sensitized solar cells (DSSC). Algae are mainly composed of chlorophylls, carotenoids, flavonoids, and Betalains, which are essential pigments that confer unique characteristics that are required in natural sensitizers. Therefore, this review aims to unveil and understand the underlying mechanism between algae pigments and photoelectrodes and to conduct a comprehensive analysis to determine the effect of algae dye on light absorption efficiency and electron transport. The structural, morphological, optical, and electrochemical impedance properties are deeply analyzed, and we show the current opportunities for natural dyes to be used in energy technologies through DSSC. A comparison of several bibliographic sources dealing with DSSC based on algae provided a general overview of the improvements in factors such as the recombination times, the filling factor, and the Voc values. The contributions of this paper relate to the conversion efficiency and future applications in the DSSC field. Finally, this review exemplifies that the nature of the pigment affects the photophysical properties of the cell. Thus, this paper may contribute to future investigations of DSSC when choosing efficient natural dyes according to their optical and electronic properties. Therefore, this work provides the knowledge required to efficiently merge materials and dyes, in which photovoltaic energy systems’ reproducibility and scalability still represent a challenge. Lastly, this document discusses the natural pigments’ stability and the approaches to improve their chemical stability.
本文系统地研究和介绍了海藻作为增敏剂的潜力。我们的目标是找到一个可行的财务策略,以提高染料敏化太阳能电池(DSSC)的全球效率。藻类主要由叶绿素、类胡萝卜素、类黄酮和甜菜素组成,它们是必需的色素,赋予天然增敏剂所需的独特特性。因此,本文旨在揭示和了解藻类色素与光电极之间的潜在机制,并对藻类染料对光吸收效率和电子传递的影响进行全面分析。深入分析了天然染料的结构、形态、光学和电化学阻抗特性,并通过DSSC展示了目前天然染料在能源技术中应用的机会。通过对几种基于藻类的DSSC的文献资料进行比较,可以对重组时间、填充因子和Voc值等因素的改进进行总体概述。本文的贡献关系到转换效率和未来在DSSC领域的应用。最后,本文综述了色素的性质对细胞光物理性质的影响。因此,本文可以为今后根据DSSC的光学和电子性质选择高效天然染料的研究提供参考。因此,这项工作提供了有效地合并材料和染料所需的知识,其中光伏能源系统的可重复性和可扩展性仍然是一个挑战。最后,本文讨论了天然色素的稳定性及提高天然色素化学稳定性的途径。
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引用次数: 0
Photocatalytic Properties of PbMoO4 Nanocrystals against Cationic and Anionic Dyes in Several Experimental Conditions 几种实验条件下PbMoO4纳米晶体对阳离子和阴离子染料的光催化性能
Pub Date : 2023-03-05 DOI: 10.3390/colorants2010008
F. Nobre, Jairo Trindade, Marcus Valério Botelho do Nascimento, G. Souza, O. Mendes, A. Albuquerque, J. Sambrano, P. Couceiro, W. Brito, Y. L. Ruiz, J. D. de Matos
This paper reports easy and fast synthesis of PbMoO4 nanocrystals by microwave-assisted hydrothermal (MH) method at different synthesis times (1, 10, 30 and 60 min) at 100 °C. X-ray diffraction, Rietveld refinement and Raman spectroscopy confirm all characteristics of diffraction peaks and active vibrational modes of the pure scheelite structure (tetragonal, I41/a) for all synthesized PbMoO4 nanocrystals. The optical bandgap calculated directly from the samples is close to 3.5 eV. The images collected by scanning electron microscopy show particles with mean length from 159.90(8) nm to 303.02(3) nm with greater exposure of planes (111), (100), (011) and (110). The photocatalytic activity of PbMoO4 nanocrystals against RhB and RBBR dyes resulted in successful degradation in short time intervals using ultraviolet light, where the best performance was achieved for the PbMoO4-10 sample, which was 29.2 and 51.8 times more effective than photolysis. The contribution of oxidant species was monitored by radical scavengers, which confirms that holes (h+) are the main oxidative species in photodegradation of RhB and RBBR dyes, while reuse of the catalyst against RhB and RBBR dyes confirms high stability of the catalyst, although recycled four times.
本文报道了微波辅助水热法(MH)在不同合成时间(1、10、30和60 min)下,在100℃条件下简便快速地合成PbMoO4纳米晶体。x射线衍射、Rietveld细化和拉曼光谱证实了所有合成的PbMoO4纳米晶体的衍射峰特征和纯白钨矿结构(四边形,I41/a)的主动振动模式。直接从样品中计算出的光学带隙接近3.5 eV。扫描电镜图像显示,颗粒平均长度为159.90(8)nm ~ 303.02(3) nm,在(111)、(100)、(011)、(110)平面曝光较大。PbMoO4纳米晶体对RhB和RBBR染料的光催化活性使其在紫外光下在短时间间隔内成功降解,其中PbMoO4-10样品的性能最佳,其效率是光解的29.2倍和51.8倍。自由基清除剂对氧化物质的贡献进行了监测,证实了空穴(h+)是RhB和RBBR染料光降解的主要氧化物质,而催化剂对RhB和RBBR染料的重复使用证实了催化剂的高稳定性,尽管循环使用了四次。
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引用次数: 0
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Colorants
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