Dyes and Pigments最新文献

{"title":"Benzylidenemalononitrile bridged long-wavelength emission luminogens with “washing-free” properties for monitoring the dynamics of LDs","authors":"Qiusi Shi ,&nbsp;Wenhao Zhao ,&nbsp;Jiale Ou,&nbsp;Longmei Yang,&nbsp;Man Chen,&nbsp;Yan Feng,&nbsp;Xiangming Meng,&nbsp;Jiaxiang Yang,&nbsp;Chengyuan Wang","doi":"10.1016/j.dyepig.2024.112459","DOIUrl":"10.1016/j.dyepig.2024.112459","url":null,"abstract":"<div><p>Understanding the physiological functions and monitoring the dynamics of lipid droplets (LDs) in living cells are crucial, because they play important roles in energy reservoir and as sources of lipid molecules, and can be potentially used as biomarkers in cancer diagnose. Organic small-molecule based luminogens with long-wavelength emission are advantageous imaging tools for visualizing the dynamics of LDs, as the long wavelength fluorescence has lower scattering and absorption by biomolecules, deeper penetration ability into tissues, and reduced interference effect. In this work, we report the design, synthesis and LDs imaging properties of two long-wavelength emitting organic luminogens (OLs) <strong>APBM</strong> and <strong>PyBM</strong>. The two materials have typical donor-acceptor-donor (D-A-D) structure with a benzylidenemalononitrile moiety as the acceptor, bridging different electron donors, i.e., <em>N</em>,<em>N</em>-dimethylamino phenyl for <strong>APBM</strong>, and pyrene for <strong>PyBM</strong>, respectively. The strong electron-withdrawing benzylidenemalononitrile moiety inducing intense intramolecular charge transfer effect, which endows the emissions of <strong>APBM</strong> and <strong>PyBM</strong> as far as 668 nm and 605 nm in the solid state, and on the other hand, creates their twisted molecular conformation. As a result, the OLs exhibit aggregation-induced-emission behaviors, due to the restriction of intramolecular motions, evolving the “washing-free” properties of the materials in bioimaging. <strong>APBM</strong> and <strong>PyBM</strong> both have low cytotoxicity and good photostability, and are able to light up HepG2 cells efficiently. In addition, <strong>APBM</strong> shows excellent LDs targeting ability, and it is successfully used to discriminate normal cells and cancer cells, and monitor the dynamics of LDs under different nutritional conditions, and the interactions with mitochondria.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112459"},"PeriodicalIF":4.1,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142243011","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}

{"title":"Highly fluorescent, water-soluble tetrapodal perylene diimides insulated by cationic pendants for live-cell imaging","authors":"Xiangkun Cui ,&nbsp;Bojun Shi ,&nbsp;Zixuan Qiu ,&nbsp;Fei Yang ,&nbsp;Xiuteng Wang ,&nbsp;Yanqing Xu ,&nbsp;Wei Wei","doi":"10.1016/j.dyepig.2024.112460","DOIUrl":"10.1016/j.dyepig.2024.112460","url":null,"abstract":"<div><p>Perylene diimides (PDIs), particularly the parent core-unsubstituted PDI chromophores, exhibit a pronounced tendency to aggregate in water, resulting in significant fluorescence quenching. Herein we present a new class of highly fluorescent, water-soluble tetrapodal PDI dyes PDI-4Py-n, with the chromophore core surrounded by four pyridinium pendants, which have been fully characterized by several techniques including X-ray crystallography. Due to the spatial isolation and charge repulsion from four cationic pendants, PDI-4Py-n can effectively suppress the chromophore aggregation in relatively concentrated aqueous solutions, thereby preserving the characteristic PDI fluorescence with high photoluminescence quantum yield. Owing to the outstanding fluorescence properties and good biocompatibility, one of <strong>PDI-4Py-n</strong> has been successfully employed as a lysosome-targetable fluorescent probe for live-cell imaging. This work presents a straightforward synthetic strategy to water-soluble non-aggregating organic dyes and highlights their potential for biomedical applications.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112460"},"PeriodicalIF":4.1,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142243012","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}

{"title":"Synthesis, characterization and application of quinoxaline-based organic dyes as anodic sensitizers in photoelectrochemical cells","authors":"Xheila Yzeiri ,&nbsp;Nicola Sangiorgi ,&nbsp;Francesca Gambassi ,&nbsp;Andrea Barbieri ,&nbsp;Massimo Calamante ,&nbsp;Daniele Franchi ,&nbsp;Carmen Coppola ,&nbsp;Adalgisa Sinicropi ,&nbsp;Barbara Ventura ,&nbsp;Alessandro Mordini ,&nbsp;Alessandra Sanson ,&nbsp;Lorenzo Zani","doi":"10.1016/j.dyepig.2024.112455","DOIUrl":"10.1016/j.dyepig.2024.112455","url":null,"abstract":"<div><p>Three new D-A-π-A organic dyes (<strong>1a-c</strong>) containing a 2,3-diphenylquinoxaline core as the main chromophore were designed to act as sensitizers for the TiO₂-based photoanode of dye-sensitized photoelectrochemical cells (DS-PEC) for water splitting. The dyes structures featured a cyanoacrylic acid group as the terminal acceptor/anchoring moiety and three different donor groups of moderate strength, namely mono- and dialkoxy-substituted benzenes, which were introduced to modulate the energies of the respective HOMO levels and enable the electron transfer from a Ru-based molecular water oxidation catalyst (WOC). Dyes <strong>1a-c</strong> were synthesized following a C–H activation strategy and fully characterized. In addition, the previously known catalyst <strong>Ru(bda)(PyP)</strong>_{<strong>2</strong>} (bda = 2,2′-bipyridine-6,6′-dicarboxylate; PyP = pyridin-4-methyl phosphonic acid) was also prepared by modification of a reported procedure. The dynamics of charge transfer processes involving the dyes adsorbed on nanocrystalline TiO₂ films were investigated by means of transient absorption spectroscopy. Photo-electrochemical experiments carried out on photoanodes functionalized with <strong>1a-c</strong> and <strong>Ru(bda)(PyP)</strong>_{<strong>2</strong>} in 0.1 M aq. Na₂SO₄ electrolyte showed the production of photocurrents up to ca. 0.15 mA cm⁻² at + 0.5 V <em>vs.</em> NHE, and highlighted how modifications of the TiO₂ staining procedure can lead to significant differences in cell performances.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112455"},"PeriodicalIF":4.1,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0143720824005217/pdfft?md5=c3dfa80b6c1a23043c665cfcc7e6e7fe&pid=1-s2.0-S0143720824005217-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142243015","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}

{"title":"Tetralactam macrocycle based aggregation-induced emission dots for selective detection of Fe3+ in water and drugs","authors":"Jian Qin ,&nbsp;Peng-Xiang Yuan ,&nbsp;Ze-Ping Xiao ,&nbsp;Rong Hu ,&nbsp;Liu-Pan Yang ,&nbsp;Huan Yao ,&nbsp;Li-Li Wang","doi":"10.1016/j.dyepig.2024.112456","DOIUrl":"10.1016/j.dyepig.2024.112456","url":null,"abstract":"<div><p>Iron ion (Fe³⁺) is crucial for both biological organisms and the environment, and iron dyshomeostasis can lead to a variety of diseases and environmental issues. Therefore, the detection of Fe³⁺ is of significant importance across various fields. For this purpose, through the co-assembly of water-soluble tetralactam macrocycle <strong>H</strong> and 1,1,2,2-tetraphenylethylene (<strong>TPE</strong>), we prepared a new type of tetralactam macrocycle based aggregation-induced emission dots (AIE-dots), namely <strong>TPE@H</strong>. <strong>TPE@H</strong> exhibitted good water-solubility and allowed the water-insoluble <strong>TPE</strong> to aggregate and exhibit strong fluorescence emission in water. Furthermore, the fluorescence of <strong>TPE@H</strong> could be quenched by Fe³⁺ through the inner filter effect, making <strong>TPE@H</strong> a potential “turn-off” fluorescent probe for Fe³⁺ detection. <strong>TPE@H</strong> exhibited a limit of detection as low as 1 μM with high selectivity, and also retained good detection performance in domestic water, human serum, and even drugs, indicating its great potential for biological and environmental monitoring of Fe³⁺. This study not only provides a green and efficient method for detecting Fe³⁺, but also expands the approach for application of water-insoluble dyes in the aqueous environment.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112456"},"PeriodicalIF":4.1,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142232655","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}

{"title":"Analyte regeneration near-infrared fluorescent probe for endogenous formaldehyde detection in living cells and in vivo","authors":"Jin-Yan Li ,&nbsp;Jing-Yan Kang ,&nbsp;Xiao-Bo Zhao ,&nbsp;Yan-Ping Shi","doi":"10.1016/j.dyepig.2024.112457","DOIUrl":"10.1016/j.dyepig.2024.112457","url":null,"abstract":"<div><p>Reaction-based fluorescent probes have proved to be promising tools for endogenous formaldehyde (FA) analysis. Among them, analyte regeneration fluorescent probes have attracted much attention due to their ability to maintain FA homeostasis in imaging analysis, but remain to be explored. Herein, we proposed a novel analyte regeneration near-infrared fluorescent probe Cy-MB for endogenous FA detection. Cy-MB was developed on the basis of hemicyanine-based NIR probe CyOH via connecting a 2-(methylamino)benzoate acid. The 2-(methylamino)benzoate in Cy-MB act not only as a fluorescence quenching group, but also a FA regeneration substrate. Such an analyte regeneration NIR probe can be specifically activated by endogenous FA, resulting in a significant fluorescence signal turn on and accompanied by FA regeneration. Probe Cy-MB possesses good analytical performance such as high selectivity and sensitivity toward FA with a detection limit at 0.67 μM. Furthermore, Cy-MB was successfully applied to image endogenous FA in cancer cells and tumor-bearing mice. Additionally, mass spectrometry imaging (MSI) was further performed to qualitatively identified the spatial distribution of the FA activation products of Cy-MB on molecules level in tumor and major organs of mice. We envision that Cy-MB will provide a widespread application in precise imaging of endogenous FA in biosystems.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112457"},"PeriodicalIF":4.1,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142243013","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}

{"title":"Expanding the horizons of photodynamic therapy: Indium metalated pyridinyl-based trans-A2B2 porphyrin as novel anti-biofilm agents","authors":"James Oyim ,&nbsp;Aviwe Magadla ,&nbsp;John Mack ,&nbsp;Edith Amuhaya ,&nbsp;Tebello Nyokong","doi":"10.1016/j.dyepig.2024.112448","DOIUrl":"10.1016/j.dyepig.2024.112448","url":null,"abstract":"<div><p>Modern medicine is exploring new approaches to combat bacterial infections associated with antibiotic-resistant bacteria and biofilms. Among these, antimicrobial photodynamic therapy (aPDT) stands out for its ability to target pathogenic microbes effectively. In this study, we investigated the antimicrobial potential of the newly synthesized indium metalated pyridinyl-based <em>trans</em>-A₂B₂ porphyrin complexes, <strong>1a,b</strong> and <strong>2a</strong>,<strong>b</strong>. The dicationic porphyrins, <strong>1b</strong> and <strong>2b,</strong> exhibited remarkable aPDT efficacy against both <em>S. aureus</em> and <em>E. coli</em> planktonic forms. Further investigation into the antimicrobial effects of the cationic porphyrins against <em>E. coli</em> and <em>S. aureus</em> biofilms revealed that both complexes (<strong>1b</strong> and <strong>2b</strong>) exhibited high efficacy in aPDT attributed to <em>tert</em>-butyl and thiophene groups that enhance photo-physicochemical properties and bacterial membrane accumulation. Scanning electron microscopy (SEM) showed disruption of cell membranes following light exposure. Our work highlights the potential of aPDT as an effective strategy for managing biofilms. By harnessing the power of these innovative compounds, we contribute to the ongoing battle against microbial threats.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112448"},"PeriodicalIF":4.1,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142243016","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}

{"title":"Multi-component synthesis and enhanced photophysical study of novel azolo[1,5-a]pyrimidine based dyes","authors":"Semen V. Aminov ,&nbsp;Victor V. Fedotov ,&nbsp;Konstantin V. Savateev ,&nbsp;Evgeny N. Ulomsky ,&nbsp;Grigory A. Kim ,&nbsp;Alexander S. Novikov ,&nbsp;Albert F. Khasanov ,&nbsp;Olga S. Taniya ,&nbsp;Ekaterina S. Starnovskaya ,&nbsp;Vasily A. Medvedev ,&nbsp;Alexey A. Kalinichev ,&nbsp;Artem S. Minin ,&nbsp;Grigory V. Zyryanov ,&nbsp;Vladimir L. Rusinov","doi":"10.1016/j.dyepig.2024.112447","DOIUrl":"10.1016/j.dyepig.2024.112447","url":null,"abstract":"<div><p>A series of novel fluorophores were obtained based on azolo[1,5-<em>a</em>]pyrimidines (APs) through multicomponent and oxidation reactions, starting from aminoazoles, morpholineacrylonitrile, and 4-(dimethylamino)benzaldehyde. Photophysical studies, as well as DFT calculations have been performed for the obtained APs. Aggregation-induced emission (AIE) phenomenon was demonstrated for fluorophores containing an aromatic substituent at the C-2 position of the azolo[1,5-<em>a</em>]pyrimidine core. It was observed that fluorophore <strong>6d</strong> exhibited reversible mechanochromic luminescence. Two-photon absorption cross-section was measured for all obtained APs. In addition, cell staining resulted in identical intracellular distribution under excitation at 405 nm, 488 nm and 561 nm.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112447"},"PeriodicalIF":4.1,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142230056","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}

{"title":"Strong and pH dependent fluorescence in unprecedented anthra[2,3-d]imidazole derivatives","authors":"Emmanuele Parisi ,&nbsp;Emanuela Santagata ,&nbsp;Alessandro Landi ,&nbsp;Roberto Centore ,&nbsp;Marco Chino ,&nbsp;Antonio Carella","doi":"10.1016/j.dyepig.2024.112440","DOIUrl":"10.1016/j.dyepig.2024.112440","url":null,"abstract":"<div><p>We here report the synthesis and characterization of three new molecules based on an unprecedented anthra [2,3-<em>d</em>]imidazole unit. The new heterocycle was unexpectedly formed while attempting to obtain 2,3-diacetamidoanthracene by reducing the corresponding anthraquinone molecules by sodium borohydride. The same reaction was successfully performed using two further different 2,3-diamidoanthraquinone derivatives, thus confirming its generality. The chemical identity of the novel molecules was also proved by realizing single crystals suitable for XRD diffraction and solving the crystalline structure of one of the prepared systems. All the molecules are strong blue emitters in ethanol, with fluorescence quantum yields around 0.40. Because of the acid-base properties of anthraimidazole ring, the optical response was investigated at different pH values. While slight differences were observed in acidic conditions, in the alkaline pH range we observed a dramatic change of the fluorescence spectra in a narrow pH range (from 11 to 13), with the color of the emission turning from blue to green. This feature makes the new class of derivatives here reported very promising as pH sensors working in strongly alkaline conditions.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112440"},"PeriodicalIF":4.1,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0143720824005060/pdfft?md5=cd850d92dcf01a76f68f9e790d48326b&pid=1-s2.0-S0143720824005060-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142162986","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}

{"title":"NIR fluorescence of phenol-π-malononitrile derivatives achieved by extending π-bridge and unexpected intermolecular deprotonation","authors":"Chunlai Yang ,&nbsp;Ying Zou ,&nbsp;Saihao Ding ,&nbsp;Shuting Fan ,&nbsp;Xinying Xu ,&nbsp;Sunbowen Zhao ,&nbsp;Yifu Huang ,&nbsp;Hefeng Zhang","doi":"10.1016/j.dyepig.2024.112438","DOIUrl":"10.1016/j.dyepig.2024.112438","url":null,"abstract":"<div><p>NIR fluorescent phenol-π-malononitrile derivatives were achieved by extending vinylene π-bridge through Wittig reaction and following Knoevenagel condensation. In addition to regular D-A effect, unexpected intermolecular deprotonation of phenol group triggered by an electron-withdrawing group on phenyl ring pushed emissions to 762 nm with a large Stokes shift up to 323 nm. The extending of π-bridge and unexpected intermolecular deprotonation of phenol group promised a feasible strategy for construction of low-molecular weight NIR fluorophores.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112438"},"PeriodicalIF":4.1,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142173214","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}

{"title":"A novel triphenylamine-based fluorescent probe for high selectivity and sensitivity detection of UO22+ in water samples and living cells","authors":"Yibin Zhang ,&nbsp;Wanxia Gao ,&nbsp;Na Zhao ,&nbsp;Meihui Wu ,&nbsp;Tong Wu ,&nbsp;Xingyu Zhang ,&nbsp;Jingran Wang ,&nbsp;Chen Wang ,&nbsp;Jinting Shang ,&nbsp;Xiji Shu","doi":"10.1016/j.dyepig.2024.112436","DOIUrl":"10.1016/j.dyepig.2024.112436","url":null,"abstract":"<div><p>Here, we report a novel triphenylamine-based fluorescent probe <strong>AIU</strong> for detecting UO₂²⁺. The probe <strong>AIU</strong> exhibited good selectivity, low detection limit (67 nm), and rapid response time(80s). The coordination mechanism of <strong>AIU</strong> toward UO₂²⁺ was investigated through theoretical calculations and other methods such as HPLC-MS. Moreover, <strong>AIU</strong> has demonstrated efficacy in detecting UO₂²⁺ in real water samples and in living cells.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"232 ","pages":"Article 112436"},"PeriodicalIF":4.1,"publicationDate":"2024-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142230057","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}