首页 > 最新文献

Dyes and Pigments最新文献

英文 中文
The unexpected and important role of alcohol stabilizer in thermal cis-trans isomerization of push-pull dyes in chloroform solution 醇稳定剂在氯仿溶液中推挽染料热顺反异构化过程中的意外重要作用
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-19 DOI: 10.1016/j.dyepig.2024.112503
Anna Sobolewska , Marcin Kozak , Jolanta Konieczkowska , Ewa Schab-Balcerzak , Stanislaw Bartkiewicz
The study demonstrates the influence of ethanol as a stabilizer in chloroform on the thermal cis-trans isomerization kinetics of photochromic compounds based on azobenzene and azopyridine derivatives. The significance of the addition of ethanol as a stabilizer in chloroform-based solutions on the isomerization reaction of the hydroxy- and the 6-hydroxylalkoxy-substituted azo compounds was investigated. The results have revealed that the presence of a polar stabilizer in a solvent can significantly reduce the reaction rate constant of the dark cis-trans isomerization due to the formation of hydrogen bonds at both ends of the azo-chromophore, thereby inhibiting the isomerization. Furthermore, a stabilizer can facilitate the reversion of azo-hydrazone tautomers of azophenols to their azobenzene form, resulting in a decrease in the reaction rate constant. The research presented in this paper can be essential for scientists who study the kinetics of the trans-cis and the cis-trans isomerization reactions of azo-chromophores. The results show that the use of solvents with polar stabilizers should be rather avoided, as their usage without information about stabilizers can lead to different experimental data. The authors should ensure that detailed information about stabilizers used in unstable solvents is included in the experimental section of their works (a detail currently often omitted in the literature).
该研究证明了乙醇作为氯仿中的稳定剂对基于偶氮苯和偶氮吡啶衍生物的光致变色化合物的热顺反异构动力学的影响。研究了在氯仿溶液中加入乙醇作为稳定剂对羟基和 6-羟基烷氧基取代偶氮化合物异构化反应的影响。研究结果表明,溶剂中极性稳定剂的存在可显著降低暗顺反异构反应的反应速率常数,这是由于偶氮色素团两端形成氢键,从而抑制了异构化反应。此外,稳定剂还能促进偶氮苯酚的偶氮腙同系物还原为偶氮苯形式,从而降低反应速率常数。对于研究偶氮色酚反式-顺式和顺式-反式异构化反应动力学的科学家来说,本文所介绍的研究非常重要。研究结果表明,应尽量避免使用带有极性稳定剂的溶剂,因为在不了解稳定剂信息的情况下使用这些溶剂会导致不同的实验数据。作者应确保在其作品的实验部分详细介绍不稳定溶剂中使用的稳定剂(目前文献中经常忽略这一细节)。
{"title":"The unexpected and important role of alcohol stabilizer in thermal cis-trans isomerization of push-pull dyes in chloroform solution","authors":"Anna Sobolewska ,&nbsp;Marcin Kozak ,&nbsp;Jolanta Konieczkowska ,&nbsp;Ewa Schab-Balcerzak ,&nbsp;Stanislaw Bartkiewicz","doi":"10.1016/j.dyepig.2024.112503","DOIUrl":"10.1016/j.dyepig.2024.112503","url":null,"abstract":"<div><div>The study demonstrates the influence of ethanol as a stabilizer in chloroform on the thermal <em>cis-trans</em> isomerization kinetics of photochromic compounds based on azobenzene and azopyridine derivatives. The significance of the addition of ethanol as a stabilizer in chloroform-based solutions on the isomerization reaction of the hydroxy- and the 6-hydroxylalkoxy-substituted azo compounds was investigated. The results have revealed that the presence of a polar stabilizer in a solvent can significantly reduce the reaction rate constant of the dark <em>cis-trans</em> isomerization due to the formation of hydrogen bonds at both ends of the azo-chromophore, thereby inhibiting the isomerization. Furthermore, a stabilizer can facilitate the reversion of azo-hydrazone tautomers of azophenols to their azobenzene form, resulting in a decrease in the reaction rate constant. The research presented in this paper can be essential for scientists who study the kinetics of the <em>trans-cis</em> and the <em>cis-trans</em> isomerization reactions of azo-chromophores. The results show that the use of solvents with polar stabilizers should be rather avoided, as their usage without information about stabilizers can lead to different experimental data. The authors should ensure that detailed information about stabilizers used in unstable solvents is included in the experimental section of their works (a detail currently often omitted in the literature).</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112503"},"PeriodicalIF":4.1,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142534827","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Orientation-dependent solvatochromism in ferrocenyl pyrimidinium conjugates: Comparative analysis and theoretical insights 二茂铁嘧啶共轭物中的定向溶色作用:比较分析和理论见解
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-19 DOI: 10.1016/j.dyepig.2024.112489
Ignacio Aburto, Matías Vidal, Sebastián Yáñez, Carolina Aliaga, Moisés Domínguez
New ferrocenyl-2-pyrimidinium solvatochromic conjugates were synthesized and their solvatochromic inverted behavior was compared to that of ferrocenyl-4-pyrimidinium dyes. These results were rationalized using EPR spectroscopy, multiparametric studies, density functional theory (DFT) calculations, and Monte Carlo simulations. The present work illustrates how a change in the orientation of the donor/acceptor pair in ferrocene-based dyes controls the solvatochromic shift ranges and inversion points, providing a new tool for the future design of ferrocenyl push-pull dyes with controlled polarity-sensing capabilities
合成了新的二茂铁基-2-嘧啶溶色共轭物,并将其溶色倒置行为与二茂铁基-4-嘧啶染料的溶色倒置行为进行了比较。利用 EPR 光谱、多参数研究、密度泛函理论 (DFT) 计算和蒙特卡罗模拟对这些结果进行了合理的解释。本研究说明了改变二茂铁基染料中供体/受体对的取向如何控制溶解变色位移范围和反转点,为将来设计具有可控极性感应能力的二茂铁基推挽染料提供了新的工具。
{"title":"Orientation-dependent solvatochromism in ferrocenyl pyrimidinium conjugates: Comparative analysis and theoretical insights","authors":"Ignacio Aburto,&nbsp;Matías Vidal,&nbsp;Sebastián Yáñez,&nbsp;Carolina Aliaga,&nbsp;Moisés Domínguez","doi":"10.1016/j.dyepig.2024.112489","DOIUrl":"10.1016/j.dyepig.2024.112489","url":null,"abstract":"<div><div>New ferrocenyl-2-pyrimidinium solvatochromic conjugates were synthesized and their solvatochromic inverted behavior was compared to that of ferrocenyl-4-pyrimidinium dyes. These results were rationalized using EPR spectroscopy, multiparametric studies, density functional theory (DFT) calculations, and Monte Carlo simulations. The present work illustrates how a change in the orientation of the donor/acceptor pair in ferrocene-based dyes controls the solvatochromic shift ranges and inversion points, providing a new tool for the future design of ferrocenyl push-pull dyes with controlled polarity-sensing capabilities</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112489"},"PeriodicalIF":4.1,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142532040","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Study of substituents-regulated dyeing properties in non-aqueous media systems based on MD simulation and DFT 基于 MD 模拟和 DFT 的非水介质体系中取代基调节染色性能的研究
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-19 DOI: 10.1016/j.dyepig.2024.112501
Hongjuan Zhang , Huiqiang Wang , Lei Ding , Bingyu Dai , Yanliang Zhang , Zhengkai Wang
To investigate the relationship between N-acetoxyethyl group and dyeing properties of disperse dyes in D5 non-aqueous medium dyeing system, the adsorption and diffusion behaviors of three disperse dyes with different structures were studied by molecular dynamics (MD). The diffusion coefficients, the planar distribution densities of dyes in different directions, and the intermolecular interaction energies were calculated. Molecular dynamics simulation (MD) was used to calculate molecules polarity index (MPI). Meanwhile, the practical dyeing experiments also were investigated to compare with simulated results. The results showed that the adsorption and diffusion behavior of disperse dyes with different structures were significantly different. Compared with dye B257, D-1 and D-2 are more easily adsorbed and diffused into the interior of the fiber because of the introduction of polar acetoxyethyl group. Moreover, the diffusion coefficient of D-2 in the fiber was relatively low, indicating that the combination between dye and polyester fiber was stable. XY plane distribution density and MPI revealed that the introduction of acetoxyethyl was beneficial to increase the adsorption amount of dye on the fiber, which was mainly related to the high binding energy between dye molecule and polyester fiber. The results of dyeing experiments showed that the decreased solubility of disperse dyes in the D5 medium was conducive to improving the dyeing rate of disperse dyes. This was consistent with the simulated interaction between dyes and D5. This study will provide a basis for further rapid and accurate development and selection of disperse dyes with high dyeing rate in non-aqueous medium systems.
为研究分散染料在D5非水介质染色体系中N-乙酰氧乙基与染色性能的关系,采用分子动力学方法研究了三种不同结构分散染料的吸附和扩散行为。计算了扩散系数、染料在不同方向上的平面分布密度以及分子间的相互作用能。利用分子动力学模拟(MD)计算了分子极性指数(MPI)。同时,还进行了实际染色实验,以与模拟结果进行比较。结果表明,不同结构的分散染料的吸附和扩散行为存在显著差异。与染料 B257 相比,D-1 和 D-2 由于引入了极性乙酰氧乙基,更容易吸附和扩散到纤维内部。此外,D-2 在纤维中的扩散系数相对较低,表明染料与聚酯纤维的结合是稳定的。XY 平面分布密度和 MPI 显示,乙酰氧乙基的引入有利于增加染料在纤维上的吸附量,这主要与染料分子与涤纶纤维之间的高结合能有关。染色实验结果表明,分散染料在 D5 介质中的溶解度降低有利于提高分散染料的上染率。这与模拟的染料与 D5 之间的相互作用相一致。这项研究将为进一步快速准确地开发和选择在非水介质体系中具有高染色率的分散染料提供依据。
{"title":"Study of substituents-regulated dyeing properties in non-aqueous media systems based on MD simulation and DFT","authors":"Hongjuan Zhang ,&nbsp;Huiqiang Wang ,&nbsp;Lei Ding ,&nbsp;Bingyu Dai ,&nbsp;Yanliang Zhang ,&nbsp;Zhengkai Wang","doi":"10.1016/j.dyepig.2024.112501","DOIUrl":"10.1016/j.dyepig.2024.112501","url":null,"abstract":"<div><div>To investigate the relationship between N-acetoxyethyl group and dyeing properties of disperse dyes in D5 non-aqueous medium dyeing system, the adsorption and diffusion behaviors of three disperse dyes with different structures were studied by molecular dynamics (MD). The diffusion coefficients, the planar distribution densities of dyes in different directions, and the intermolecular interaction energies were calculated. Molecular dynamics simulation (MD) was used to calculate molecules polarity index (MPI). Meanwhile, the practical dyeing experiments also were investigated to compare with simulated results. The results showed that the adsorption and diffusion behavior of disperse dyes with different structures were significantly different. Compared with dye B257, D-1 and D-2 are more easily adsorbed and diffused into the interior of the fiber because of the introduction of polar acetoxyethyl group. Moreover, the diffusion coefficient of D-2 in the fiber was relatively low, indicating that the combination between dye and polyester fiber was stable. XY plane distribution density and MPI revealed that the introduction of acetoxyethyl was beneficial to increase the adsorption amount of dye on the fiber, which was mainly related to the high binding energy between dye molecule and polyester fiber. The results of dyeing experiments showed that the decreased solubility of disperse dyes in the D5 medium was conducive to improving the dyeing rate of disperse dyes. This was consistent with the simulated interaction between dyes and D5. This study will provide a basis for further rapid and accurate development and selection of disperse dyes with high dyeing rate in non-aqueous medium systems.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112501"},"PeriodicalIF":4.1,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142534258","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Triad photosensitizers based on iodo-aza-Bodipy and naphthalenediimides (NDI) with broadband absorption: Study of resonance energy transfer and electron transfer 基于碘-氮-波地平和具有宽带吸收的萘二亚胺(NDI)的三元光敏剂:共振能量转移和电子转移研究
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-19 DOI: 10.1016/j.dyepig.2024.112499
Jie Ma , Fangming Zhao , Yanbing Yin , Yingying Li , Di Wu , Guangming Yin , Xiaohui Gao
Two organic photosensitizers based on resonance energy transfer (A-1 and A-2) are prepared. Naphthalenediimides was used as intramolecular energy donor and iodo-aza-Bodipy was used as intramolecular energy acceptor/spin converter. A-1 (ε = 42,800 at 618 nm and ε = 59,600 at 674 nm) and A-2 (ε = 33,300 at 514 nm and ε = 68,300 at 674 nm) give the two strong absorption band and both of them show broadband absorption in visible region. The photophysical properties of the compounds were studied with steady state and time-resolved spectroscopy in detail. With steady state and time-resolved spectroscopy, we found that photoexcitation into the energy donor was followed by singlet energy transfer, then via the intersystem crossing (ISC) of the energy acceptor. By nanosecond time-resolved transient absorption spectroscopy and DFT calculation, triplet excited state is localized on the iodo-aza-Bodipy moiety. Quantum yield of singlet oxygen of A-1 and A-2 is 39.7 % and 40.9 %, respectively. Based on fluorescence lifetime quenching, the efficiency of intramolecular energy transfer is estimated to be 15.9 % and 27.7 % for A-1 and A-2. And PET is responsible for the relatively low efficiency, which is identified by the calculation of kcs/kFRET and the Gibbs free energy change (△G0cs). A-1 and A-2 were used for singlet oxygen (1O2) mediated photooxidation of 1,5-dihydroxylnaphthalene and the photosensitizing ability are more efficient than the triplet photosensitizers with the mono-chromophore photosensitizer.
制备了两种基于共振能量转移的有机光敏剂(A-1 和 A-2)。萘二甲酰亚胺用作分子内能量供体,碘-氮-联苯胺用作分子内能量受体/自旋转换器。A-1 (ε = 42,800 波长,波长 618 纳米;ε = 59,600 波长,波长 674 纳米)和 A-2(ε = 33,300 波长,波长 514 纳米;ε = 68,300 波长,波长 674 纳米)给出了两个强吸收带,并且都在可见光区域显示出宽带吸收。利用稳态光谱和时间分辨光谱详细研究了这些化合物的光物理特性。通过稳态光谱和时间分辨光谱,我们发现光激发进入能量供体后会发生单线能量转移,然后通过能量受体的系统间交叉(ISC)进行能量转移。通过纳秒时间分辨瞬态吸收光谱和 DFT 计算,三重激发态被定位在碘-氮-联二吡分子上。A-1 和 A-2 的单线态氧量子产率分别为 39.7% 和 40.9%。根据荧光寿命淬灭,估计 A-1 和 A-2 分子内能量转移的效率分别为 15.9% 和 27.7%。通过计算 kcs/kFRET 和吉布斯自由能变化(△G0cs),可以确定 PET 是造成相对较低效率的原因。A-1和A-2用于单线态氧(1O2)介导的1,5-二羟基萘的光氧化,其光敏能力比单色素光敏剂的三重光敏剂更有效。
{"title":"Triad photosensitizers based on iodo-aza-Bodipy and naphthalenediimides (NDI) with broadband absorption: Study of resonance energy transfer and electron transfer","authors":"Jie Ma ,&nbsp;Fangming Zhao ,&nbsp;Yanbing Yin ,&nbsp;Yingying Li ,&nbsp;Di Wu ,&nbsp;Guangming Yin ,&nbsp;Xiaohui Gao","doi":"10.1016/j.dyepig.2024.112499","DOIUrl":"10.1016/j.dyepig.2024.112499","url":null,"abstract":"<div><div>Two organic photosensitizers based on resonance energy transfer (<strong>A-1</strong> and <strong>A-2</strong>) are prepared. Naphthalenediimides was used as intramolecular energy donor and iodo-aza-Bodipy was used as intramolecular energy acceptor/spin converter. <strong>A-1</strong> (<em>ε</em> = 42,800 at 618 nm and <em>ε</em> = 59,600 at 674 nm) and <strong>A-2</strong> (<em>ε</em> = 33,300 at 514 nm and <em>ε</em> = 68,300 at 674 nm) give the two strong absorption band and both of them show broadband absorption in visible region. The photophysical properties of the compounds were studied with steady state and time-resolved spectroscopy in detail. With steady state and time-resolved spectroscopy, we found that photoexcitation into the energy donor was followed by singlet energy transfer, then via the intersystem crossing (ISC) of the energy acceptor. By nanosecond time-resolved transient absorption spectroscopy and DFT calculation, triplet excited state is localized on the iodo-aza-Bodipy moiety. Quantum yield of singlet oxygen of <strong>A-1</strong> and <strong>A-2</strong> is 39.7 % and 40.9 %, respectively. Based on fluorescence lifetime quenching, the efficiency of intramolecular energy transfer is estimated to be 15.9 % and 27.7 % for <strong>A-1</strong> and <strong>A-2</strong>. And PET is responsible for the relatively low efficiency, which is identified by the calculation of <em>k</em><sub>cs</sub>/<em>k</em><sub>FRET</sub> and the Gibbs free energy change (△G<sup>0</sup><sub>cs</sub>). <strong>A-1</strong> and <strong>A-2</strong> were used for singlet oxygen (<sup>1</sup>O<sub>2</sub>) mediated photooxidation of 1,5-dihydroxylnaphthalene and the photosensitizing ability are more efficient than the triplet photosensitizers with the mono-chromophore photosensitizer.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112499"},"PeriodicalIF":4.1,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142532039","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Phosphorescent cyclometalated Ir(III) complexes with fluoranthene unit and their near-infrared (NIR) OLEDs showing NIR% higher than 99 % 具有荧蒽单元的磷光环甲基化铱(III)配合物及其近红外 (NIR) 有机发光二极管(NIR%高于 99
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-19 DOI: 10.1016/j.dyepig.2024.112500
Hongyan Wang, Ruiqin Zhu, Zhao Feng, Daokun Zhong, Ziyi Chen, Bochao Su, Yuanhui Sun, Xiaolong Yang, Guijiang Zhou
With the aim to design and synthesize cyclometalated Ir(III) complexes with near-infrared (NIR) emission, a series of ppy-type ligands with fluoranthene unit have been synthesized bearing different aromatic nitrogen heterocycles of isoquinoline, quinoline, pyridine and benzo [d]thiazole. With these organic ligands, four [Ir (ppy)2 (acac)] complexes are prepared named as IrFTIQ, IrFTQL, IrFTPY and IrFTBZ. In solution, IrFTIQ can emit NIR phosphorescence at 738 nm, while IrFTQL (ca. 692 nm), IrFTPY (ca. 670 nm) and IrFTBZ (ca. 690 nm) are typical deep-red emitters. It should be noted that all these fluoranthene-based cyclometalated Ir(III) complexes show good electrochemical stability indicated by their reversible redox procedures. When doped in the emission layer of OLEDs, IrFTIQ and IrFTBZ can furnish NIR electroluminescence (EL) at 748 nm and 700 nm, respectively, while the devices with IrFTPY as emitter can furnish deep-red EL. Critically, the optimized OLED doped with IrFTIQ can achieve maximum external quantum efficiency (EQE) as high as 5.01 % and a radiance up to 6284 mW Sr−1 m−2. Critically, the NIR OLEDs based on IrFTIQ can furnish EL with NIR component (NIR%) of a total spectrum > 99 %. All these encouraging results definitely demonstrate the effectiveness of our molecular design strategy for the new-type Ir(III) NIR phosphorescent complexes and the great potential of the fluoranthene group in developing high-performance Ir-based NIR phosphors for OLEDs.
为了设计和合成具有近红外发射的环甲基化 Ir(III) 配合物,我们合成了一系列带有荧蒽单元的PY 型配体,这些配体含有异喹啉、喹啉、吡啶和苯并 [d]噻唑等不同的芳香氮杂环。利用这些有机配体制备了四种[Ir (ppy)2 (acac)] 复合物,分别命名为 IrFTIQ、IrFTQL、IrFTPY 和 IrFTBZ。在溶液中,IrFTIQ 可以发出 738 纳米的近红外磷光,而 IrFTQL(约 692 纳米)、IrFTPY(约 670 纳米)和 IrFTBZ(约 690 纳米)则是典型的深红色发光体。值得注意的是,所有这些基于荧蒽的环金属化 Ir(III) 复合物都具有良好的电化学稳定性,其可逆氧化还原过程表明了这一点。当掺杂到有机发光二极管的发射层时,IrFTIQ 和 IrFTBZ 可分别在 748 纳米和 700 纳米波长处发出近红外电致发光(EL),而以 IrFTPY 作为发射体的器件则可发出深红色 EL。重要的是,掺杂了 IrFTIQ 的优化 OLED 可实现高达 5.01 % 的最大外部量子效率 (EQE),辐射量高达 6284 mW Sr-1 m-2。更重要的是,基于 IrFTIQ 的近红外有机发光二极管可以提供总光谱为 99% 的近红外成分(NIR%)电致发光。所有这些令人鼓舞的结果无疑证明了我们的新型 Ir(III)近红外磷光配合物分子设计策略的有效性,以及荧蒽基团在开发用于 OLED 的高性能 Ir 基近红外荧光粉方面的巨大潜力。
{"title":"Phosphorescent cyclometalated Ir(III) complexes with fluoranthene unit and their near-infrared (NIR) OLEDs showing NIR% higher than 99 %","authors":"Hongyan Wang,&nbsp;Ruiqin Zhu,&nbsp;Zhao Feng,&nbsp;Daokun Zhong,&nbsp;Ziyi Chen,&nbsp;Bochao Su,&nbsp;Yuanhui Sun,&nbsp;Xiaolong Yang,&nbsp;Guijiang Zhou","doi":"10.1016/j.dyepig.2024.112500","DOIUrl":"10.1016/j.dyepig.2024.112500","url":null,"abstract":"<div><div>With the aim to design and synthesize cyclometalated Ir(III) complexes with near-infrared (NIR) emission, a series of ppy-type ligands with fluoranthene unit have been synthesized bearing different aromatic nitrogen heterocycles of isoquinoline, quinoline, pyridine and benzo [<em>d</em>]thiazole. With these organic ligands, four [Ir (ppy)<sub>2</sub> (acac)] complexes are prepared named as <strong>IrFTIQ</strong>, <strong>IrFTQL</strong>, <strong>IrFTPY</strong> and <strong>IrFTBZ</strong>. In solution, <strong>IrFTIQ</strong> can emit NIR phosphorescence at 738 nm, while <strong>IrFTQL</strong> (<em>ca.</em> 692 nm), <strong>IrFTPY</strong> (<em>ca.</em> 670 nm) and <strong>IrFTBZ</strong> (<em>ca.</em> 690 nm) are typical deep-red emitters. It should be noted that all these fluoranthene-based cyclometalated Ir(III) complexes show good electrochemical stability indicated by their reversible redox procedures. When doped in the emission layer of OLEDs, <strong>IrFTIQ</strong> and <strong>IrFTBZ</strong> can furnish NIR electroluminescence (EL) at 748 nm and 700 nm, respectively, while the devices with <strong>IrFTPY</strong> as emitter can furnish deep-red EL. Critically, the optimized OLED doped with <strong>IrFTIQ</strong> can achieve maximum external quantum efficiency (EQE) as high as 5.01 % and a radiance up to 6284 mW Sr<sup>−1</sup> m<sup>−2</sup>. Critically, the NIR OLEDs based on <strong>IrFTIQ</strong> can furnish EL with NIR component (NIR%) of a total spectrum <em>&gt;</em> 99 %. All these encouraging results definitely demonstrate the effectiveness of our molecular design strategy for the new-type Ir(III) NIR phosphorescent complexes and the great potential of the fluoranthene group in developing high-performance Ir-based NIR phosphors for OLEDs.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112500"},"PeriodicalIF":4.1,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142534831","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Unmasking the role of anion-π bonding - A new paradigm for iodide selective organic probes 揭示阴离子-π键的作用--碘化物选择性有机探针的新范例
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-18 DOI: 10.1016/j.dyepig.2024.112498
Gopal Balamurugan , Wei Zhang , Ye Won Choi , Ji Min Park , Sivan Velmathi , Jong S. Park
This review article undiscloses the significance of anion-π bonding in iodide-selective supramolecular chemosensors. Due to their lower basicity and nucleophilicity, iodide-selective chemosensors have received less attention than other halide ions. However, several supramolecular organic sensors have emerged by utilizing the larger size of the iodide anion, allowing it to fit into the receptor's cavity or pseudo-cavity readily. Therein, it was frequently presented that iodide-selective sensors typically involved new charge transfer bands in absorbance spectra and a fluorescence quenching, closely resembling the effects of anion-π non-covalent interactions. This review article meticulously explores the substantial evidence confirming the presence of anion-π bonding between the host and guest molecules. The current discovery has the potential to usher in a new paradigm in designing and exploring supramolecular detectors based on anion-π bonding. It should also be emphasized that an important objective is to create awareness among scientists about the less common anion-π bonding and its versatile applications toward anion recognition, non-covalent organic frameworks, and self-assemblies.
这篇综述文章揭示了阴离子-π键在碘化物选择性超分子化学传感器中的重要作用。与其他卤化离子相比,碘离子选择性化学传感器由于其较低的碱性和亲核性而较少受到关注。不过,一些超分子有机传感器利用了碘阴离子的较大尺寸,使其能够轻易地进入受体的空腔或伪空腔。其中,碘化物选择性传感器通常会在吸光度光谱中产生新的电荷转移带和荧光淬灭,这与阴离子-π非共价相互作用的效果非常相似。这篇综述文章细致地探讨了大量证据,证实宿主分子和客体分子之间存在阴离子-π键。目前的发现有可能为设计和探索基于阴离子-π键的超分子探测器开创一个新范例。还应该强调的是,我们的一个重要目标是让科学家们认识到不太常见的阴离子-π键及其在阴离子识别、非共价有机框架和自组装方面的广泛应用。
{"title":"Unmasking the role of anion-π bonding - A new paradigm for iodide selective organic probes","authors":"Gopal Balamurugan ,&nbsp;Wei Zhang ,&nbsp;Ye Won Choi ,&nbsp;Ji Min Park ,&nbsp;Sivan Velmathi ,&nbsp;Jong S. Park","doi":"10.1016/j.dyepig.2024.112498","DOIUrl":"10.1016/j.dyepig.2024.112498","url":null,"abstract":"<div><div>This review article undiscloses the significance of anion-π bonding in iodide-selective supramolecular chemosensors. Due to their lower basicity and nucleophilicity, iodide-selective chemosensors have received less attention than other halide ions. However, several supramolecular organic sensors have emerged by utilizing the larger size of the iodide anion, allowing it to fit into the receptor's cavity or pseudo-cavity readily. Therein, it was frequently presented that iodide-selective sensors typically involved new charge transfer bands in absorbance spectra and a fluorescence quenching, closely resembling the effects of anion-π non-covalent interactions. This review article meticulously explores the substantial evidence confirming the presence of anion-π bonding between the host and guest molecules. The current discovery has the potential to usher in a new paradigm in designing and exploring supramolecular detectors based on anion-π bonding. It should also be emphasized that an important objective is to create awareness among scientists about the less common anion-π bonding and its versatile applications toward anion recognition, non-covalent organic frameworks, and self-assemblies.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112498"},"PeriodicalIF":4.1,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142534829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photochemical and electrochemical behavior of a molecular probe: Fluorescence on-off-on response to detect multiple ions (Cu2+, ClO− and CN−) with different rate of reaction 分子探针的光化学和电化学行为:检测具有不同反应速率的多种离子(Cu2+、ClO- 和 CN-)的荧光开关响应
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-18 DOI: 10.1016/j.dyepig.2024.112492
Mohammed Kaleem , Ravisen Rai , Rimpi Bhandari , Hirdyesh Mishra , Arvind Misra
A molecular probe 3 containing phenyl substituted imidazolyl unit and diaminomaleonitrile (DAMN) moiety has been synthesized and characterized. Photophysical and electrochemical behavior probe 3 were studied in partial aqueous medium (ACN/H2O, 9.5:0.5 v/v). Probe 3 upon interaction with different class of ions showed sensitivity for Cu2+, ClO and CN ions with different response time and reaction rates due to variation in intramolecular charge transfer (ICT) process. Both Cu2+ and ClO ions displayed enhanced emission due to hydrolysis of imine bond to form compound 2 in the medium whereas, with CN fluorescence quenching was observed due to the deprotonation of –OH/–NH2 functions. The kinetic and optical behavior of the probe suggested that interaction occurred in two steps with Cu2+ (complexation and hydrolysis; absk1,2,3(Cu2+) = 1.17, 0.74 and 0.06 s−1) and ClO (hydrolysis and deprotonation; absk1,2(ClO) = 3.0 and 0.60 s−1) ions while CN (absk1,2(CN) = 2.13 and 1.66 s−1) induces deprotonation in one step. The interaction of probe 3 with ClO was relatively fast than with Cu2+/CN ions. Job's plot analysis between probe 3 and ions revealed a 1:1 (Cu2+/ClO) and 1:2 (CN) ratio stoichiometry with good limit of detection (nM) and binding affinity (LOD, 17; KCu2+ = 3.23 × 106 M−1; LOD, 18.5; KClO = 5.23 × 105 M−1 and LOD, 23.2; KCN = 5.50 × 109 M−2) respectively. Probe 3 displayed a naked–eye sensitive fluorescence response to detect tested ions on test paper strips and good recovery percentage of ions in real water sample analysis.
一种含有苯基取代咪唑单元和二氨基马来腈(DAMN)分子的分子探针 3 已被合成并表征出来。在部分水介质(ACN/H2O,9.5:0.5 v/v)中对探针 3 的光物理和电化学行为进行了研究。由于分子内电荷转移(ICT)过程的变化,探针 3 与不同种类的离子相互作用时,对 Cu2+、ClO- 和 CN- 离子表现出不同的灵敏度,反应时间和反应速率也不同。Cu2+ 和 ClO- 离子在介质中因水解亚胺键形成化合物 2 而显示出更强的发射,而 CN- 离子则因 -OH/-NH2 功能的去质子化而观察到荧光淬灭。探针的动力学和光学行为表明,与 Cu2+ 离子(络合和水解;absk1,2,3(Cu2+) = 1.17、0.74 和 0.06 s-1)和 ClO- 离子(水解和去质子化;absk1,2(ClO-) = 3.0 和 0.60 s-1)的相互作用分两步进行,而与 CN- 离子(absk1,2(CN-) = 2.13 和 1.66 s-1)的去质子化作用只需一步。探针 3 与 ClO- 的相互作用比与 Cu2+/CN- 离子的相互作用快。探针 3 与离子之间的约伯图分析表明,两者的化学计量比分别为 1:1(Cu2+/ClO-)和 1:2(CN-),具有良好的检测限(nM)和结合亲和力(LOD,17;KCu2+ = 3.23 × 106 M-1;LOD,18.5;KClO- = 5.23 × 105 M-1 和 LOD,23.2;KCN- = 5.50 × 109 M-2)。探针 3 显示出肉眼灵敏的荧光反应,可检测试纸条上的受测离子,并在实际水样分析中显示出良好的离子回收率。
{"title":"Photochemical and electrochemical behavior of a molecular probe: Fluorescence on-off-on response to detect multiple ions (Cu2+, ClO− and CN−) with different rate of reaction","authors":"Mohammed Kaleem ,&nbsp;Ravisen Rai ,&nbsp;Rimpi Bhandari ,&nbsp;Hirdyesh Mishra ,&nbsp;Arvind Misra","doi":"10.1016/j.dyepig.2024.112492","DOIUrl":"10.1016/j.dyepig.2024.112492","url":null,"abstract":"<div><div>A molecular probe <strong>3</strong> containing phenyl substituted imidazolyl unit and diaminomaleonitrile (DAMN) moiety has been synthesized and characterized. Photophysical and electrochemical behavior probe <strong>3</strong> were studied in partial aqueous medium (ACN/H<sub>2</sub>O, 9.5:0.5 v/v). Probe <strong>3</strong> upon interaction with different class of ions showed sensitivity for Cu<sup>2+</sup>, ClO<sup>−</sup> and CN<sup>−</sup> ions with different response time and reaction rates due to variation in intramolecular charge transfer (ICT) process. Both Cu<sup>2+</sup> and ClO<sup>−</sup> ions displayed enhanced emission due to hydrolysis of imine bond to form compound <strong>2</strong> in the medium whereas, with CN<sup>−</sup> fluorescence quenching was observed due to the deprotonation of –OH/–NH<sub>2</sub> functions. The kinetic and optical behavior of the probe suggested that interaction occurred in two steps with Cu<sup>2+</sup> (complexation and hydrolysis; <sup>abs</sup><em>k</em><sub><em>1</em></sub><sub>,</sub><sub><em>2</em></sub><sub>,</sub><sub><em>3</em>(Cu</sub><sup>2+</sup><sub>)</sub> = 1.17, 0.74 and 0.06 s<sup>−1</sup>) and ClO<sup>−</sup> (hydrolysis and deprotonation; <sup>abs</sup><em>k</em><sub><em>1</em></sub><sub>,</sub><sub><em>2</em>(ClO</sub>−<sub>)</sub> = 3.0 and 0.60 s−<sup>1</sup>) ions while CN<sup>−</sup> (<sup>abs</sup><em>k</em><sub><em>1</em></sub><sub>,</sub><sub><em>2</em></sub><sub>(</sub><sub>CN</sub>−<sub>)</sub> = 2.13 and 1.66 s<sup>−1</sup>) induces deprotonation in one step. The interaction of probe <strong>3</strong> with ClO<sup>−</sup> was relatively fast than with Cu<sup>2+</sup>/CN<sup>−</sup> ions. Job's plot analysis between probe <strong>3</strong> and ions revealed a 1:1 (Cu<sup>2+</sup>/ClO<sup>−</sup>) and 1:2 (CN<sup>−</sup>) ratio stoichiometry with good limit of detection (nM) and binding affinity (<em>LOD,</em> 17; <em>K</em><sub>Cu</sub><sup>2+</sup> = 3.23 × 10<sup>6</sup> M<sup>−1</sup>; <em>LOD</em>, 18.5; <em>K</em><sub>ClO</sub><sup>−</sup> = 5.23 × 10<sup>5</sup> M<sup>−1</sup> and <em>LOD</em>, 23.2; <em>K</em><sub>CN</sub><sup>−</sup> = 5.50 × 10<sup>9</sup> M<sup>−2</sup>) respectively. Probe <strong>3</strong> displayed a naked–eye sensitive fluorescence response to detect tested ions on test paper strips and good recovery percentage of ions in real water sample analysis.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112492"},"PeriodicalIF":4.1,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142534259","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Prussian blue-EGCG nanoparticles for synergistic photothermal and chemo anticancer therapy in vitro 用于体外协同光热和化疗抗癌疗法的普鲁士蓝-EGCG 纳米粒子
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-17 DOI: 10.1016/j.dyepig.2024.112487
Bingquan Chen , Manni Wu , Jiayi Qin , Ling Zhang , Xianying Cao , Ke Jiang
Photothermal therapy (PTT) is an innovative cancer treatment that converts light into heat to induce tumor cell death. Compared to traditional therapies, PTT is minimally invasive, has low drug resistance, and targets tumors with high specificity. However, its standalone use is limited due to potential tumor adaptation to heat and the risk of collateral damage to healthy tissues. Combining PTT with chemotherapy could overcome these challenges. Prussian blue (PB) is a promising photothermal agent due to its strong near-infrared absorption and excellent heat conversion properties, but its small pore size restricts the loading of therapeutic agents. This study introduces a novel nanosystem that modifies PB with an Fe-EGCG polyphenol nano-layer to enhance drug delivery capabilities. The system effectively inhibited cancer cell growth in vitro under low-power near-infrared laser exposure, achieving up to 75 % inhibition by combining mild-temperature (44 °C) photothermal therapy with chemotherapy. This approach offers a viable strategy for integrating non-porous materials into synergistic cancer treatments.
光热疗法(PTT)是一种创新的癌症治疗方法,它能将光转化为热,诱导肿瘤细胞死亡。与传统疗法相比,光热疗法创伤小、耐药性低、靶向肿瘤的特异性高。然而,由于肿瘤对热的潜在适应性以及对健康组织造成附带损害的风险,其单独使用受到了限制。将 PTT 与化疗相结合可以克服这些挑战。普鲁士蓝(PB)具有很强的近红外吸收能力和出色的热转换特性,是一种很有前景的光热剂,但其孔径较小,限制了治疗剂的装载。本研究介绍了一种新型纳米系统,该系统用 Fe-EGCG 多酚纳米层对紫外蓝进行改性,以增强药物输送能力。该系统在低功率近红外激光照射下有效抑制了体外癌细胞的生长,通过将低温(44 °C)光热疗法与化疗相结合,达到了高达 75% 的抑制率。这种方法为将无孔材料整合到癌症协同治疗中提供了一种可行的策略。
{"title":"Prussian blue-EGCG nanoparticles for synergistic photothermal and chemo anticancer therapy in vitro","authors":"Bingquan Chen ,&nbsp;Manni Wu ,&nbsp;Jiayi Qin ,&nbsp;Ling Zhang ,&nbsp;Xianying Cao ,&nbsp;Ke Jiang","doi":"10.1016/j.dyepig.2024.112487","DOIUrl":"10.1016/j.dyepig.2024.112487","url":null,"abstract":"<div><div>Photothermal therapy (PTT) is an innovative cancer treatment that converts light into heat to induce tumor cell death. Compared to traditional therapies, PTT is minimally invasive, has low drug resistance, and targets tumors with high specificity. However, its standalone use is limited due to potential tumor adaptation to heat and the risk of collateral damage to healthy tissues. Combining PTT with chemotherapy could overcome these challenges. Prussian blue (PB) is a promising photothermal agent due to its strong near-infrared absorption and excellent heat conversion properties, but its small pore size restricts the loading of therapeutic agents. This study introduces a novel nanosystem that modifies PB with an Fe-EGCG polyphenol nano-layer to enhance drug delivery capabilities. The system effectively inhibited cancer cell growth in vitro under low-power near-infrared laser exposure, achieving up to 75 % inhibition by combining mild-temperature (44 °C) photothermal therapy with chemotherapy. This approach offers a viable strategy for integrating non-porous materials into synergistic cancer treatments.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112487"},"PeriodicalIF":4.1,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142534825","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of novel pyranoflavylium-based dyes as promising photosensitizers for antimicrobial photodynamic inactivation 合成新型吡喃黄基染料,作为抗菌光动力灭活的理想光敏剂
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-17 DOI: 10.1016/j.dyepig.2024.112495
Paula Araújo, Patrícia Correia, Nuno Mateus, Victor de Freitas, Iva Fernandes, Luís Cruz, Joana Oliveira
Amino-substituted dyes have recently been described for their interesting photosensitizing properties in photodynamic therapy against bacterial growth. In the present study, two novel pyranoflavylium-based dyes namely 4′-dimethylamino-10-(4''-(dimethylamino)phenyl)pyranoflavylium (4′,4″N(Me)2PyF) and 6-Bromo-4′-dimethylamino-10-(4''-(dimethylamino)phenyl)pyranoflavylium (6Br4′,4″N(Me)2PyF) were synthesized through the reactions between salicylaldehyde and acetophenone derivatives to improve the photo-properties of 5-hydroxy-4′-dimethylaminoflavylium (5OH4′N(Me)2F), a non-photoactivated flavylium salt previously reported due to the presence of a hydroxyl group in its structure. The presence of a pyranic ring with an additional dimethylaminophenyl group and the insertion of a bromine atom changed the spectroscopic properties of the parent flavylium, causing a red shift of the absorption band, higher molar extinction coefficient, and fluorescence emission. Both pyranoflavylium dyes showed appreciable singlet oxygen production, and phototoxicity studies demonstrated their photoactivable nature, leading to a reduction of >3log in cellular viability of S. aureus ATCC 29213 after 15 min of irradiation (22.5 J/cm2).
In conclusion, this study describes a chemical strategy to extend π-conjugation, converting a non-active flavylium dye into photoactivable ones. This approach could be further explored to develop novel solutions for antimicrobial photodynamic inactivation, potentially addressing issues related to antimicrobial resistance.
最近,有人描述了氨基取代染料在针对细菌生长的光动力疗法中有趣的光敏特性。在本研究中,两种新型吡喃黄基染料,即 4′-二甲基氨基-10-(4''-(二甲基氨基)苯基)吡喃黄基(4′,4″N(Me)2PyF)和 6-溴-4′-二甲基氨基-10-(4''-(二甲基氨基)苯基)吡喃黄基(6Br4′、4″N(Me)2PyF)的光性质。由于吡喃环上多了一个二甲基氨基苯基基团,并插入了一个溴原子,母黄烷的光谱特性发生了变化,导致吸收带红移、摩尔消光系数升高和荧光发射。这两种吡喃黄基染料都显示出明显的单线态氧产生,光毒性研究证明了它们的光活性性质,经过 15 分钟的照射(22.5 J/cm2)后,金黄色葡萄球菌 ATCC 29213 的细胞活力降低了 >3log。可以进一步探索这种方法,为抗菌剂光动力灭活开发新的解决方案,从而有可能解决与抗菌剂耐药性有关的问题。
{"title":"Synthesis of novel pyranoflavylium-based dyes as promising photosensitizers for antimicrobial photodynamic inactivation","authors":"Paula Araújo,&nbsp;Patrícia Correia,&nbsp;Nuno Mateus,&nbsp;Victor de Freitas,&nbsp;Iva Fernandes,&nbsp;Luís Cruz,&nbsp;Joana Oliveira","doi":"10.1016/j.dyepig.2024.112495","DOIUrl":"10.1016/j.dyepig.2024.112495","url":null,"abstract":"<div><div>Amino-substituted dyes have recently been described for their interesting photosensitizing properties in photodynamic therapy against bacterial growth. In the present study, two novel pyranoflavylium-based dyes namely 4′-dimethylamino-10-(4''-(dimethylamino)phenyl)pyranoflavylium (4′,4″N(Me)<sub>2</sub>PyF) and 6-Bromo-4′-dimethylamino-10-(4''-(dimethylamino)phenyl)pyranoflavylium (6Br4′,4″N(Me)<sub>2</sub>PyF) were synthesized through the reactions between salicylaldehyde and acetophenone derivatives to improve the photo-properties of 5-hydroxy-4′-dimethylaminoflavylium (5OH4′N(Me)<sub>2</sub>F), a non-photoactivated flavylium salt previously reported due to the presence of a hydroxyl group in its structure. The presence of a pyranic ring with an additional dimethylaminophenyl group and the insertion of a bromine atom changed the spectroscopic properties of the parent flavylium, causing a red shift of the absorption band, higher molar extinction coefficient, and fluorescence emission. Both pyranoflavylium dyes showed appreciable singlet oxygen production, and phototoxicity studies demonstrated their photoactivable nature, leading to a reduction of &gt;3log in cellular viability of <em>S. aureus</em> ATCC 29213 after 15 min of irradiation (22.5 J/cm<sup>2</sup>).</div><div>In conclusion, this study describes a chemical strategy to extend π-conjugation, converting a non-active flavylium dye into photoactivable ones. This approach could be further explored to develop novel solutions for antimicrobial photodynamic inactivation, potentially addressing issues related to antimicrobial resistance.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"233 ","pages":"Article 112495"},"PeriodicalIF":4.1,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142571362","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A novel fluorescent probe based on indole-fused 1,8-naphthalimide derivative for rapid discrimination of H2S, Cys, and Hcy/GSH and its multi-functional applications 一种基于吲哚融合 1,8萘二甲酰亚胺衍生物的新型荧光探针,用于快速鉴别 H2S、Cys 和 Hcy/GSH 及其多功能应用
IF 4.1 3区 工程技术 Q2 CHEMISTRY, APPLIED Pub Date : 2024-10-16 DOI: 10.1016/j.dyepig.2024.112494
Guifen Lu , Sihan Ding , Yaohui Wang , Suci Meng , Yiming Zhang
In view of the vital roles in biological systems, it is significant and challenging to construct a fluorescent probe that can simultaneously detect and discriminate the most important four reactive sulfur species (H2S, Cys, Hcy/GSH). Herein, a smart fluorescent probe Indole-NI-NBD based on indole-fused 1,8-naphthalimide derivative has been rationally designed and synthesized. This probe displayed fast, selective and sensitive responses for these four reactive sulfur species with distinct fluorescent turn-on signal changes at 595 nm. Moreover, the unique absorbance enhancement at 575 nm and the distinct color change achieved “naked eye” detection of H2S. The distinctive fluorescence enhancement at 560 nm only for Cys achieved its discrimination from H2S, and Hcy/GSH. More importantly, using Indole-NI-NBD-loaded test strips and RGB experiment, a smartphone sensing platform was constructed and realized the convenient, reliable, and on-site detection of H2S and Cys. Finally, Indole-NI-NBD was applied to image H2S, Cys, Hcy/GSH and distinguish Cys from them in living cells and zebrafish via different fluorescence signals at a single excitation wavelength.
鉴于硫在生物系统中的重要作用,构建一种能同时检测和鉴别最重要的四种活性硫(H2S、Cys、Hcy/GSH)的荧光探针具有重要意义和挑战性。在此,我们合理地设计并合成了一种基于吲哚融合 1,8萘二甲酰亚胺衍生物的智能荧光探针 Indole-NI-NBD。该探针对这四种活性硫具有快速、选择性和灵敏的反应,在 595 纳米波长处具有明显的荧光开启信号变化。此外,575 纳米波长处独特的吸光度增强和明显的颜色变化实现了对 H2S 的 "肉眼 "检测。Cys 在 560 纳米波长处的独特荧光增强实现了与 H2S 和 Hcy/GSH 的区分。更重要的是,利用加载了 Indole-NI-NBD 的试纸和 RGB 实验,构建了一个智能手机传感平台,实现了对 H2S 和 Cys 便捷、可靠的现场检测。最后,应用 Indole-NI-NBD 对活细胞和斑马鱼中的 H2S、Cys、Hcy/GSH 进行成像,并通过单一激发波长下的不同荧光信号区分 Cys。
{"title":"A novel fluorescent probe based on indole-fused 1,8-naphthalimide derivative for rapid discrimination of H2S, Cys, and Hcy/GSH and its multi-functional applications","authors":"Guifen Lu ,&nbsp;Sihan Ding ,&nbsp;Yaohui Wang ,&nbsp;Suci Meng ,&nbsp;Yiming Zhang","doi":"10.1016/j.dyepig.2024.112494","DOIUrl":"10.1016/j.dyepig.2024.112494","url":null,"abstract":"<div><div>In view of the vital roles in biological systems, it is significant and challenging to construct a fluorescent probe that can simultaneously detect and discriminate the most important four reactive sulfur species (H<sub>2</sub>S, Cys, Hcy/GSH). Herein, a smart fluorescent probe <strong>Indole-NI-NBD</strong> based on indole-fused 1,8-naphthalimide derivative has been rationally designed and synthesized. This probe displayed fast, selective and sensitive responses for these four reactive sulfur species with distinct fluorescent turn-on signal changes at 595 nm. Moreover, the unique absorbance enhancement at 575 nm and the distinct color change achieved “naked eye” detection of H<sub>2</sub>S. The distinctive fluorescence enhancement at 560 nm only for Cys achieved its discrimination from H<sub>2</sub>S, and Hcy/GSH. More importantly, using <strong>Indole-NI-NBD</strong>-loaded test strips and RGB experiment, a smartphone sensing platform was constructed and realized the convenient, reliable, and on-site detection of H<sub>2</sub>S and Cys. Finally, <strong>Indole-NI-NBD</strong> was applied to image H<sub>2</sub>S, Cys, Hcy/GSH and distinguish Cys from them in living cells and zebrafish <em>via</em> different fluorescence signals at a single excitation wavelength.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112494"},"PeriodicalIF":4.1,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142534684","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
期刊
Dyes and Pigments
全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1