Dyes and Pigments最新文献

{"title":"Synthesis, crystal structure, and sensing properties for Fe3+, Al3+, Cu2+, MnO4−, Cr2O72− and p-nitroaniline based on a 2D Cd coordination polymer","authors":"Zan Sun ,&nbsp;Yinong Liang ,&nbsp;Yarong Xu ,&nbsp;Kaixin Zhang","doi":"10.1016/j.dyepig.2025.112764","DOIUrl":"10.1016/j.dyepig.2025.112764","url":null,"abstract":"<div><div>A two dimension Cd coordination polymer, namely [Cd(CPPCA) (H₂O)₂]_n (<strong>Cd-CPPCA</strong>, H₂CPPCA = 1-(4-carbxoylphenyl)piperidine-4-caboylic acid) has been synthesized under a simple one-step solvothermal process. <strong>Cd-CPPCA</strong> crystallizes in monoclinic crystal system <em>P</em>2₁/<em>c</em> space group with <em>a</em> = 14.1188 (6) Å, <em>b</em> = 7.7599 (4) Å, <em>c</em> = 12.7353 (6) Å and <em>β</em> = 93.505 (4) °. <strong>Cd-CPPCA</strong> adopts a 2-nodal 2D net with a schläfli symbol of {8⁴.12²}{8}₂. The 3D supramolecular structure of <strong>Cd-CPPCA</strong> was constructed <em>via</em> hydrogen bond (O–H⋯O) and π<strong>···</strong>π interaction between adjacent layers. As a promising sensing material, <strong>Cd-CPPCA</strong> exhibit excellent sensing ability for Fe³⁺, Cu²⁺, Al³⁺, MnO₄⁻, Cr₂O₇²⁻, <em>p</em>-nitroaniline (<em>p</em>-NA) with highly sensitivity, excellent recyclability and lower detection limits. The possible sensing mechanism was also discussed.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112764"},"PeriodicalIF":4.1,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644255","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":"ACQ-to-AIE modulation through delicate donor-acceptor switch strategy for multi-functional AIEgens applications","authors":"Weiwei Zhang ,&nbsp;Yu Cheng ,&nbsp;Bing Xu ,&nbsp;Yuejie Luo ,&nbsp;Xuejing Su ,&nbsp;Jingming Zhou ,&nbsp;Xia Wang ,&nbsp;Tong Wu ,&nbsp;Nannan Chen ,&nbsp;Hongqiang Qiu ,&nbsp;Xiaoping Wu ,&nbsp;Lijun Xie","doi":"10.1016/j.dyepig.2025.112750","DOIUrl":"10.1016/j.dyepig.2025.112750","url":null,"abstract":"<div><div>The development of novel aggregation-induced emission luminogens (AIEgens) has been a hot research topic due to their promising applications in biosensors, organic light-emitting diodes (OLEDs) and data storage, etc. In this study, two new rofecoxib derivatives, <strong>QE-DA</strong> and <strong>QE-D</strong> were successfully developed as novel AIEgens by exchanging the donor-acceptor (D-A) position or migrating the position of electron donor (D) group based on the fluorescent aggregation-caused quenching (ACQ) structure of (<em>Z</em>)-5-benzylidene-3-(4-isocyanophenyl)-4-phenylfuran-2(5<em>H</em>)-one (<strong>QE</strong>). Next, single crystal X-ray analysis of <strong>QE, QE-DA</strong> and <strong>QE-D</strong> revealed that their molecular conformations and packing modes were mainly responsible for the AIE or ACQ behavior. Specifically, <strong>QE</strong> exhibits ACQ behavior, while <strong>QE-DA</strong> and <strong>QE-D</strong> display AIE behavior. These differences are determined based on key parameters such as the displacement angle (<em>θ</em>₁) and vertical distance (<em>d</em>). In addition, <strong>QE-DA</strong> and <strong>QE-D</strong> also showed solvatochromic effects as well as acidochromic properties with good reversible multi-stimulus behaviors. Moreover, their potential applications such as pH and water sensors as well as specific probes targeting lipid droplets (R = 0.98) were fully investigated. Taken together, this study provides two new design philosophies for achieving ACQ-to-AIE conversion by migrating the position of the D group or switching the position of D and A groups, and further presents the potential of these targets to be developed as water sensors, security ink and LDs-targeting probes.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112750"},"PeriodicalIF":4.1,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143678414","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":"Dinaphtho[1,2-a:1′,2′-h]anthracene diimides: Synthesis, properties, and visualization of latent fingerprint application","authors":"Caihang Zhang,&nbsp;Hepeng Duan,&nbsp;Bingshan Zhang,&nbsp;Ping Deng,&nbsp;Yan Yu","doi":"10.1016/j.dyepig.2025.112754","DOIUrl":"10.1016/j.dyepig.2025.112754","url":null,"abstract":"<div><div>Imide-functionalized polycyclic aromatic hydrocarbons (PAHs) endow fascinating optoelectronic properties, rendering them suitable for many applications. Developing these new kinds of functional materials is interesting and challenging. Dinaphtho[1,2-a:1′,2′-h]anthracene (DNphA), a non-planar S-shaped double helical helicene within the PAH class, has received relatively little research. In this contribution, a series of solution-processable DNphA diimide derivative dyes (<strong>M1</strong>∼<strong>M5</strong>) were designed and synthesized. The density functional theory calculation, photophysical and electrochemical properties of the new fluorescent dyes have been investigated. Notably, <strong>M5</strong> was used as a fluorescent developer for latent fingerprint visualization, where fingerprints on different substrates displayed clear yellow-green fluorescence. This research provides insights into the efficient design strategy of the imide functionalization of DNphA and the synthesis and application of DNphA diimide-based functional dyes.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112754"},"PeriodicalIF":4.1,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143679016","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":"Colorimetric recognition and adsorption of 1,4-benzoquinone using amine-functionalized polyacrylonitrile fibers","authors":"Xuehua Zhang ,&nbsp;Haocheng Sun ,&nbsp;Xiaoting Li ,&nbsp;Jian Cao ,&nbsp;Ning Ma ,&nbsp;Minli Tao ,&nbsp;Wenqin Zhang","doi":"10.1016/j.dyepig.2025.112768","DOIUrl":"10.1016/j.dyepig.2025.112768","url":null,"abstract":"<div><div>Various amine-functionalized polyacrylonitrile fibers (PAN_EF, PAN_PF, PAN_BF, PAN_NPF, and PAN_DNPF) were prepared and employed to detect and adsorb 1,4-benzoquinone. After comparing the different types of amines and different carbon chain lengths, the most evident color change was observed in PAN_NPF. This material possessed a suitable carbon chain length, strong alkalinity, and an adsorption capacity of up to 1.32 mol mol⁻¹. Following its immersion in a 1,4-benzoquinone solution for 30 s, PAN_NPF rapidly changed from yellow to dark brown. This interaction between amine and 1,4-benzoquinone was quick, rendering this approach effective for real-time monitoring. Moreover, PAN_NPF was highly effective in detecting 1,4-benzoquinone in water across a wide pH range (3–10), with a detection limit as low as 0.5 ppm. PAN_NPF maintained its sensitivity and underwent stable color changes even at low temperatures (0 °C), and the presence of ions and compounds in practical applications did not interfere with its discoloration behavior. The kinetic and isotherm curves revealed that the adsorption process was consistent with the Langmuir isothermal adsorption and pseudo-second-order kinetic models, demonstrating the chemical adsorption of 1,4-benzoquinone by PAN_NPF. These findings highlight the superior detection capabilities of PAN_NPF, rendering it an efficient and reliable material for environmental monitoring and water purification.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112768"},"PeriodicalIF":4.1,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644254","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":"Modification of perylene red pigments with graphene oxide","authors":"Dongjun Lv ,&nbsp;Furui Jia ,&nbsp;Xiaolei Zhang ,&nbsp;Chenwei Qu ,&nbsp;Ying Xu ,&nbsp;Qiuya Li ,&nbsp;Yuexing Zhang ,&nbsp;Lingyun Cao","doi":"10.1016/j.dyepig.2025.112758","DOIUrl":"10.1016/j.dyepig.2025.112758","url":null,"abstract":"<div><div>This study employed monolayer graphene oxide to modify the surface of perylene pigments C.I. Pigment Red 179 and C.I. Pigment Red 149 via ball milling in a solvent medium, aiming to improve their performance. The composition and structure of modified pigments were determined and characterized with scanning electron microscopy (SEM), X-ray powder diffraction (XRD), and X-ray photoelectron spectroscopy (XPS), and their fluorescence properties, specific surface area, thermal stability, particle size distribution, color characteristics, water contact angle, and dispersion stability were assessed. In addition, the adsorption structure and electronic properties of graphene oxide on the surface of perylene red pigment molecules, as well as the interaction behavior of perylene red pigment molecules with graphene oxide, were explained by density functional theory (DFT) calculations. Results showed non-covalent interactions between perylene red pigments and monolayer graphene oxide, leading to a more concentrated particle size distribution, enhanced yellow hue, and increased color strength to 104.3 %–117.1 %. The interaction distance between the two components was approximately 3.6 Å.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112758"},"PeriodicalIF":4.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143637617","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":"19F NMR-based lithium sensors using 19F-Labeled aza-crown ethers: Regioisomeric and substituent effects","authors":"Donghyeon Lee ,&nbsp;Yanchuan Zhao ,&nbsp;Byungjin Koo","doi":"10.1016/j.dyepig.2025.112762","DOIUrl":"10.1016/j.dyepig.2025.112762","url":null,"abstract":"<div><div>We herein report ¹⁹F NMR-based molecular lithium sensors using ¹⁹F-labeled aza-crown ether derivatives and investigate the regioisomeric and substituent effects on ¹⁹F NMR lithium sensing. Four new fluorinated 1-aza-12-crown-4 derivatives were successfully synthesized via Buchwald-Hartwig amination. Fluorine substitution at the <em>para</em> position relative to the 1-aza-12-crown-4 moiety resulted in a 20-fold increase in chemical shift differences upon exposure to lithium ions, compared to the <em>meta</em> position. We also found that an electron-withdrawing nitro group on the fluorobenzene aza-crown ether prevented any ¹⁹F NMR chemical shifts upon exposure to lithium ions. In contrast, a methyl substituent at the same position as the nitro group induced remarkable (∼20 fold) chemical shifts, similar to the compound without any functional group. In addition, magnesium and calcium, two divalent metal ions prevalent in lithium-containing geothermal brines, were able to bind to <strong>ParaF</strong>, resulting in ¹⁹F NMR chemical shifts. The slow exchange between <strong>ParaF</strong> and magnesium enabled the simultaneous detection of lithium (which undergoes rapid exchange) and magnesium when both ions were present. This work provides a rational design principle for developing highly selective molecular lithium sensors.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112762"},"PeriodicalIF":4.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143627815","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 “building-block” strategy for porphyrin-based two-photon photosensitizers dual-targeting cancer cells and subcellular organelles","authors":"Chaorui Su ,&nbsp;Peipei Xing ,&nbsp;Jinghui Zhang ,&nbsp;Xiaolin Ma ,&nbsp;Chang Sun ,&nbsp;Mengliang Zhu ,&nbsp;Yingxian Li ,&nbsp;Hongwu Du ,&nbsp;Yongzhong Bian","doi":"10.1016/j.dyepig.2025.112759","DOIUrl":"10.1016/j.dyepig.2025.112759","url":null,"abstract":"<div><div>In this paper, by employing a “building-block” strategy, we present the design and synthesis of <strong>ABMP(Zn)</strong>, a novel two-photon and dual-targeted photosensitizer developed for fluorescence imaging and photodynamic therapy (PDT). In this approach, biotin and morpholine groups were incorporated to a porphyrin core to achieve specific targeting of cancer cells and lysosomes, respectively. Furthermore, the two-photon absorption fluorophore AceDAN was introduced to enable two-photon excitation. Upon 740 nm excitation, the efficient Förster Resonance Energy Transfer from AceDAN to the porphyrin core results in red fluorescence emission for imaging and singlet oxygen (¹O₂) for PDT. <strong>ABMP(Zn)</strong> demonstrated effective cancer cell and lysosomal localization, high phototoxicity, low dark toxicity, and the capability to induce and monitor cellular morphological changes under two-photon excitation, which highlight <strong>ABMP(Zn)</strong> as a promising agent for precise cancer theranostics.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112759"},"PeriodicalIF":4.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143679018","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":"Unlocking the secrets of historical violet hues: A spectroscopic and mass spectrometric investigation of logwood ink recipes","authors":"Adele Ferretti ,&nbsp;Eva Vermeersch ,&nbsp;Francesca Sabatini ,&nbsp;Ilaria Degano ,&nbsp;Peter Vandenabeele","doi":"10.1016/j.dyepig.2025.112757","DOIUrl":"10.1016/j.dyepig.2025.112757","url":null,"abstract":"<div><div>The spread of logwood bark (<em>Heamatoxylum campechianum</em> L.) in Europe as a dyestuff dates back to the 16^th century, while its integration into ink formulations only began in the 19^th century (<em>logwood inks</em>). Renowned for their broad spectrum of achievable colours and their non-corrosive impact on paper, logwood inks have been used by many artists, for instance by Impressionists in their drawings. This work investigates the gap in the literature related to the chemical composition of logwood-based inks, specifically focusing on the comprehensive characterisation of dye components and the influence of recipes on the inks molecular profile. Several 19^th-20^th century formulations of logwood inks, differing in inorganic salts, additives and pre-oxidation time, were selected and reproduced according to historical recipes. Colourimetric measurements enabled us to evaluate the chromatic differences of logwood-based inks produced following historical methods. Instead, the organic component was investigated on reference mock-ups by analytical methods based on micro-Raman spectroscopy and liquid chromatography coupled to diode array detection (HPLC-DAD) and high-resolution tandem mass spectrometry (HPLC-ESI-Q-ToF) after suitable sample treatments. Raman analysis revealed significative shifts in vibrational modes of dyes depending on the inorganic salts used in the recipes, providing a unique fingerprint able of distinguishing alum-, alum/copper-, iron-, and chrome-based logwood inks. Additionally, HPLC-DAD and HPLC-ESI-Q-ToF enabled us to expand the dataset of molecular markers available for logwood inks identification, by tentatively assigning the structure of compounds never or seldom reported in the literature (G-compounds and hematein derivatives). The potential synergy of spectroscopic and chromatographic techniques was also explored, allowing us to achieve valuable insights on the oxidation pathway of <em>hematoxylin</em> to <em>hematein</em> (both C.I. 75290) in relation to the ink recipes. The proposed method is particularly valuable in forensic and heritage science, where the composition of inks can offer crucial insights into the origin and authenticity of documents or artworks.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112757"},"PeriodicalIF":4.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143678400","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":"Extending the conjugation of xanthene through N heteroatoms","authors":"Daniel J. Frazier,&nbsp;Daniel M. Knauss","doi":"10.1016/j.dyepig.2025.112760","DOIUrl":"10.1016/j.dyepig.2025.112760","url":null,"abstract":"<div><div>Polymers with small molecule chromophores incorporated into the conjugated backbone have shown excellent electronic properties for use in organic semiconductor applications. The incorporation of xanthene moieties, the central motif in fluorescein and rhodamine dyes, into a fully conjugated polymer backbone has yet to be fully investigated due to the inherent break in conjugation within the structure. This study reports the syntheses of four different low-molecular weight polymers via Buchwald-Hartwig polyamination composed of xanthene units linked through various amines. The N heteroatom linkage promotes conversion to the quinoidal form, which extends the conjugation through a hypothesized zwitterionic backbone. Evidence of extended conjugation is seen in the reduced optical band gaps of the polymers with the lowest band gap observed at 1.58 eV. Furthermore, air stable unpaired electrons were detected via electron paramagnetic resonance (EPR), suggesting a stabilized equilibrium between ionic and radical forms in the backbone. The design and characteristics inherent in the materials synthesized should provide intrinsic electrical conductivity and magnetic properties of interest.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112760"},"PeriodicalIF":4.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143641958","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 sensitive fluorescence probe for accurate detection of peroxynitrite in mitochondria and imaging inflammation sites","authors":"Xiao-Lei Xue ,&nbsp;Ru-Xing Chen ,&nbsp;Jun-Yu Luan ,&nbsp;Ying-Ying Shan ,&nbsp;Kun-Peng Wang ,&nbsp;Xiao-Zhong Xiang ,&nbsp;Ying Fang ,&nbsp;Shaojin Chen ,&nbsp;Zhi-Qiang Hu","doi":"10.1016/j.dyepig.2025.112756","DOIUrl":"10.1016/j.dyepig.2025.112756","url":null,"abstract":"<div><div>Peroxynitrite (ONOO⁻) plays a pivotal role in various physiological and pathological processes. The sensitive and specific detection of ONOO⁻ is of paramount significance for early diagnosis, treatment, and prognosis of diseases. In this study, a near-infrared (NIR) fluorescent probe was developed for the detection of ONOO⁻ with rapid responsiveness (less than 100 s). As the concentration of ONOO⁻ increases, the ratio of fluorescence intensities exhibited a robust linear relationship with ONOO⁻ concentration. Additionally, the probe demonstrated the ability to selectively detect changes in ONOO⁻ levels, with a limit of detection (LOD) value of 13 nM. Importantly, the probe was successfully employed to detect endogenous ONOO⁻ in living cells and mouse models. In conclusion, the fluorescent probe exhibits significant potential for elucidating disease processes induced by ONOO⁻.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"239 ","pages":"Article 112756"},"PeriodicalIF":4.1,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143637618","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}