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Dyes and Pigments
Elsevier Applied Science Publishers Ltd.
Dyes and Pigments

Elsevier Applied Science Publishers Ltd.

0143-7208

Dyes and Pigments/Journal Dyes and PigmentsSCICCRISTPEIAHCI
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    Near-infrared fluorescence probe with a large Stokes shift for selectively imaging of hydrogen peroxide in living cells and in vivo

    Meng-Jiao GaoYun HuaJia-Qi Xu
    8页
    查看更多>>摘要：In this work, we have designed and synthesized a large stokes shift and near-infrared (NIR) probe DCM-HNU for visualization of H2O2 in both living HeLa cells and zebra fish. The probe DCM-HNU was structured based on phenylborate pincinol ester as the recognition group connecting DCM-OH via nucleophilic substitution reaction. The probe possessed large stokes shift (205 run), near-infrared (NIR) emission (658 nm). 0.17 |jM detection Limit, 10,550 L-mol cm~(-1) molar extinction coefficient, 2.06 x 10~(-3) S~(-1) reaction rate constant, and excellent selectivity proved the condition for practical application. There was a good linear relationship between fluorescence intensity and H2O2 concentration from 0 to 200 uM (R2 = 0.9955) to facilitate quantitative analysis of H2O2. More importantly, the probe is able to visualize exogenous and endogenous H2O2 in living HeLa cells and zebra fish. The superior properties of the probe provide potential for exploring the function and participation of H2O2 in biological systems.
      原文链接:
    • NSTL

    Synthesis and evaluation of new fluorinated pyropheophorbide-a derivatives for photodynamic therapy

    Feng WangYinghua GaoJiahui Zhang
    9页
    查看更多>>摘要：The discovery of new photosensitizers with excellent photodynamic anti-tumor effects remains a challenge for photodynamic therapy and diagnosis. Here a series of chlorophyll derivatives containing fluorine-substituted alkyl side chain were designed and synthesized. These compounds exhibited strong absorption at 660-665 nm with excellent molar extinction coefficients. Their singlet oxygen generation ability was also proved to be excellent. Upon excitation with a 411 nm laser, strong fluorescence emission around 660-670 nm was observed. They also showed obvious photodynamic antitumor activity to A549 cell in vitro and to tumor-bearing mice in vivo. Their photodynamic anti-proliferative abilities were confirmed in vivo with histotomy. Flow cytometry test showed that new compounds could induce late period cell apoptosis or necrosis. Sub-organelle localization test indicated that they primarily localized in the endoplasmic reticulum. Among them, compound F-C4-Ppa possesses the most outstanding anti-tumor effect and therefore, it is a promising anti-tumor drug candidate in photodynamic therapy and photo-imaging diagnosis.
      原文链接:
    • NSTL

    Using fullerene as the third component to boosting the photovoltaic performances of pyran acceptor

    Miao LiMingyue YuLisi Yang
    7页
    查看更多>>摘要：Ternary blend strategy has been proved to be an effective method to improve the photovoltaic performance for organic solar cells (OSCs). In this work, efficient ternary OSCs are fabricated with one donor PBDB-T and two acceptors Ph-DTDP-TIC and PC71BM. Ternary components can form a cascade energy level alignment when PC71BM as the third component to enhance charge transfer between the non-fullerene acceptor Pft-DTDP-TIC and PC71BM, achieving improved charge separation and collection in the ternary OSCs. Meanwhile, it demonstrated that PC71BM as the third component can also improve the morphology of the active layer and form suitable phase separation scale. As a results, two binary devices (PBDB-T:Ph-DTDP-TIC and PBDB-T:PC_(71)BM) exhibit moderate power conversion efficiencies (PCEs) of 8.80% and 6.74%, respectively. While, the optimized PBDB-T:Ph-DTDP-TIC:PC_(71)BM ternary device can produce an enhanced PCE of 11.07% through adding 40 wt% PC71BM in acceptors, originating from simultaneously improved J_(sc) of 17.57 mA/cm2 and FF of 70.90%. Our work demonstrated the ternary strategy with PC71BM as the third component can promote charge transfer and transport to improve photovoltaic performance for OSCs.
      原文链接:
    • NSTL

    Excited-state photodynamics of pyrene-containing boronated dyes

    Mateusz UrbanKrzysztof DurkaArtur Kasprzak
    11页
    查看更多>>摘要：Three pyrene-containing boronated dyes have been examined in order to evaluate the effect of pyrene moiety localization on the photophysical properties. (3-Fluorophenyl)-l-pyreneborinic 8-oxyquinolinate was obtained by reacting 1-lithiopyrene with 3-fluorophenylboronic diethyl ester followed by complexation with 8-hydroxy-quinoline. This compound consists of a pyrene unit (Py) directly bonded to a boron-quinolinate moiety (BQ). Two diarylborinic complexes (boranils) with salicylaldimine ligands (SA) bearing a pyrene moiety were obtained by reacting bis(2,6-difluorophenyl)borinic ethyl ester with salicylaldehyde and 1-aminopyrene or N~1-(pyren-l-ylmethyl)benzene-l,4-diamine. The first compound consists of pyrene unit directly bonded to the boron-containing boranil moiety (BA), while the other consists of a pyrene unit connected to the BA moiety via a 1-amino-4-methylenearninophenyl linker. The obtained compounds were characterized by ~1H and ~(13)C NMR spectroscopy and X-ray crystallography. UV-Vis fluorescence measurements showed the strong influence of solvent on the observed emission maximum {X_(max)) and quantum yield of emission. For (3-fluorophenyl)-l-pyr-eneborinic 8-oxyquinolinate the excited pyrene unit lead to dual fluorescence (from Py and BQ) which was modulated by solvent polarity. The possible formation of the open form of this complex via B-N bond breakage influences strongly the photoinduced processes which was supported by the fluorescence lifetimes measurements and quantum mechanical calculations. For two boranils the BA emission was observed upon excitation of pyrene regardless on solvent polarity. In die case of boranil complex containing l-amino-4-methyleneaminophenyl linker a significant increase in quantum yield in the solid state was observed which may be attributed to aggregation-induced emission.
      原文链接:
    • NSTL

    A facile method to identify anthraquinone dyes in textile artworks using galvanic displacement based-SERS substrates

    Jian LiuFeng ZhaoJuan Zhu
    6页
    查看更多>>摘要：We present here a novel strategy for textile sample treatment, using galvanic displacement-based substrates, to identify anthraquinone dyes by surface enhanced Raman spectroscopy (SERS). This global procedure of SERS analysis, using several silver microparticles, in particularly those of dendritic shape, formed by reducing silver nitrate with zinc or copper, can be accomplished within 20 min. Compared to the synthesis of standard Lee-Meisel colloids, the preparation of silver dendrites provides a simple, fast and cost-effective route to produce reliable SERS substrates. The most fascinating feature is that the textile fibers analyzed are almost simultaneously covered with the substrates once the galvanic displacement reaction is triggered. This method was successfully applied to discriminating between alizarin and purpurin in a 6th-9th century samite with bird roundels, and carminic acid and laccaic acid in a 1740s chinoiserie brocade. However, as is the case with other silver substrates, the Raman signals of the insect dyes normally overlapped those of the plant dyes in the SERS profiles.
      原文链接:
    • NSTL

    Preparation and property optimization of bistable electrochromic microcapsules

    Chengcheng WangJiashuang LiLiping Zhang
    8页
    查看更多>>摘要：In the improvement of stability and lifetime of bistable electrochromic (EC) materials, the microcapsule technique was used to protect the EC materials in a polymer shell, which was named bistable EC microcapsules (BEC-Ms). However, the particle size and shell thickness of microcapsules will affect their properties, such as response time, coloration efficiency, and bistable property. In this study, BEC-Ms was prepared via solvent evaporation method filled with PMMA as the shell and the mixture of crystal violet lactone (CVL), tetrabutylammonium perchlorate (TBAP), and phase change material (PCM) as the core. The particle size and shell thickness of microcapsules were adjusted and systematically investigated by controlling the emulsification rate and mass ratio of polymer shell to core. The optimized BEC-Ms with 2 urn size and 22.94 nm thickness showed excellent performance including fast response time (about 1 s), far lower than the safety of human body drive voltage (2 V), coloration efficiency (932 cm~2 C~(-1)), and good bistability (216 h). This approach provides a viable and alternative to flexible energy-efficient wearable display-related devices and smart textiles.
      原文链接:
    • NSTL

    Cationic porphyrazines with morpholinoethyl substituents-Syntheses, optical properties, and photocytotoxicities

    Paulina Skupin-MrugalskaTomasz KoczorowskiWojciech Szczolko
    12页
    查看更多>>摘要：Novel cationic water-soluble magnesium(II) and zinc(II) sulfanyl porphyrazines with peripheral N-methyl-morpholinoethyl iodide moieties in the form of iodide salts were synthesized and characterized with ESI MS, UV-Vis, and NMR. The subsequent logP0/w values were lower for octaiodide salts than those for their neutral precursors and, therefore the macrocycles were considered hydrophilic. After measuring the binding constants Kb, it becomes clear that the obtained cationic porphyrazines, as well as the neutral porphyrazines, were poor liposome binders. The cationic water-soluble magnesium(II) and zinc(II) sulfanyl porphyrazines revealed moderate singlet oxygen generation yields and higher susceptibility to decomposition after light exposition. In the antimicrobial studies, magnesium(II) porphyrazine with peripheral N-methylmorpholinoethyl groups presented a log reduction up to 6.5 against Gram-positive bacteria. In vitro, photocytotoxic activity assessments of mag-nesium(II) and zinc(II) porphyrazines with peripheral N-methylmorpholinoethyl, as well as magnesium(IQ sulfanyl porphyrazine derivative in the form of iodide salt, were performed on two types of oral cancer cells-SCC-25 and CAL-27. Zinc(II) sulfanyl porphyrazine with peripheral N-methylmorpholinoethyl groups decreased the viability of the SCC-25 cell line after light irradiation with IC50 at 6.46 uM in its free form and at 3.61 nM after encapsulation in liposomal formulation. The opposite phenomenon was observed for magnesium(II) sulfanyl porphyrazine with peripheral N-methylmorpholfnoethyl groups. The magnesium(II) sulfanyl porphyrazine derivative in the form of iodide salt did not demonstrate any photocytotoxicity in the studied cell lines.
      原文链接:
    • NSTL

    A corrole-based fluorescent probe for detection of sulfur ion and its application in living cells

    Guifen LuYongjie GaoXiaochun Wang
    8页
    查看更多>>摘要：A dual signaling probe DPC-O-NBD formed through the conjugation of 5,15-bis(phenyl)-10-(4-hydroxylphenyl)-corrole (DPC-OH) with 4-chloro-7-nitrobe-nzo-2-oxa-l,3-diazole (NBD-C1) is explored to detect sulfur ion (S~(2-)). The key design principle is based on the nucleophilicity of S~(2-), which can be used to cleave the bridging ether bond in the probe to obtain both fluorogenic and chromogenic signaling behaviors. Importantly, the probe DPC-O-NBD not only showed a high sensitivity (LOD: 48 nM) and selectivity over other interfering species, but also exhibited a rapid response (—18 s) towards S~(2-). Furthermore, DPC-O-NBD can also be used to detect S~(2-) in both water and live cells, providing a potentially powerful approach for probing S~(2-) chemistry in biological systems.
      原文链接:
    • NSTL

    Origin of indigo colorants revealed by ion mobility spectrometry coupled to mass spectrometry followed by supervised classification

    Volodymyr PaukJana MichalcakovaKlara Jagosova
    12页
    查看更多>>摘要：Identification of colorants is a key theme in art history and restoration. Indigo, the famous blue dye and pigment, was historically produced from four biological sources cultivated in specific parts of the world: woad in Europe, true indigo in Indian region, anil in South and Central America, and Japanese indigo in Eastern Asia. Therefore, identification of the biological source of indigo could reveal the provenance of pigments and dyes used in historical artworks, assist evaluation of their age, and help to trace ancient trade routes. To date, none of the previous reports achieved confident identification of indigo sources. This is the first systematic comprehensive untargeted workflow for discrimination of indigo colorants from different biological sources. Besides die new analytical procedure based on flow injection analysis and high-resolution mass spectrometry coupled to ion mobility spectrometry, the original multi-method screening scheme for feature selection, classification model training, and validation is presented. Reference indigo pigments were analyzed neat or embedded into appropriate binders to simulate oil painting or egg tempera mural. Combinations of eight feature selection methods (information gain, information gain ratio, Gini decrease, ANOVA, Chi squared, ReliefF, fast correlation based filter, and significance analysis of microarrays) and five classification algorithms (k-nearest neighbors, support-vector machines, random forest, neural network, and naive Bayes) were evaluated via double (nested) cross-validation. The best performance was achieved with random forest across all feature selection methods (average classification accuracy 94%, negative ionization mode data). Tentative substance classes were proposed for the most important features based on their mass fragmentation patterns. A methylated flavonoid (diosmetin) and an indole alkaloid (2,2'-biindolyl) were identified in woad and true indigo pigments, respectively, and confirmed by chromatography. Plant sources of colorants were determined in historical samples of oil paintings and textiles.
      原文链接:
    • NSTL

    Efficient and reversible acidofluorochromic features on a solid platform for reusable security writing: A structure-property relationship study on anthracenyl π-conjugates

    Shouvik BhuinPralok K. SamantaManab Chakravarty
    13页
    查看更多>>摘要：Reversible solid-state acidochromic (SSAC) behavior offers facile and handy fluorescence (FL)-based pH detection and secured ink or rewritable platform for anti-counterfeiting applications. The acidochromism based detection primarily depends on the pyridine-based linkers in the solution state but remains ill-defined in the solid-state. This work describes the degree of emission responses, primarily in the solid-state if the N-atom of pyridyl ring alters the position in toluene/thiophene-connected structurally twisted anthracenyl it-conjugates. The role of N-atom at the 4th position is more sensitive against acid fumes, especially in the thiophene-linked analog that displays 108 nm redshift, compared to the toluene analog (85 nm). Changing N-atom's position from 4th to 3rd in the ring, only tolyl-linked analog is significantly responsive with 48 nm redshift. Single-crystal structures of protonated molecules have been judiciously determined and found more planar compared to the originals. The crystal structure and molecular packing analyses dictate that the rotors are significantly twisted with multiple noncovalent interactions, crucially responsible for the admirable solid-state emission. The gained planarity of the molecules upon protonation can elucidate the redshifted emission with quenching. Further, stronger H-bonding and excited state stabilization for a few pyridinium salts may be accountable for reducing the emission intensity and redshifted emission, respectively. High-contrast emission color variation on protonation-deprotonation has been employed as a handy polymer-blended emitting platform for convenient and reusable security writings.
      原文链接:
    • NSTL