Polymeric Dye Research Articles

Charge-by-Charge Ion Pairing Preserves Fluorescence Emission

In this issue of Chem, Flood and co-workers demonstrate spatially and electronically isolated cationic dyes in crystalline charge-by-charge ion-pairing systems based on sandwiched [2 + 1]-type anion complexes of a π-electronic cyanostar macrocycle; these dyes exhibit fluorescent colors and intensities similar to those in solution.

Ion-selective reversing aggregation-caused quenching - Maximizing optodes signal stability

An alternative optical signal transduction mechanism for ion-selective optodes is proposed. The nanostructural sensors benefit from ion-selective reversing aggregation caused quenching yielding turn-on, bright and highly stable optical signals. Selective incorporation of analyte results in transformation of the polymer dye from aggregate to a micelle structure, affecting spatial arrangement of chromophore groups in the nanostructure. Formation of micelles, induced by ion-selective interactions, is coupled with pronounced increase of emission due to decrease of aggregation caused quenching, characteristic for dispersed phase formation. The formed micelles are highly stable in solution, offering constant in time (days scale) emission signal. The important difference from other known systems is that the analyte binding induced change does not affect the chromophore group, but occurs in distant, terminal position of the side chain of the polymer.As a model system calcium selective optodes have been prepared. Thus obtained probes were characterized with broad analyte concentration range (from 10−7 to 10−3 M) emission signal increase. The turn-on response was observed within broad range of pH (6.3–8.9), with no sign of optical signal deterioration during 5 days contact with the analyte or more than two weeks storage.

Synthesis and Properties of Polyurethane - Dispersed Diazo Black GNN Polymer Dye

Polyurethane - Dispersed Diazo Black GNN Polymer dye (PU-DDB GNN) was synthesized by incorporation of DDB GNN into polyurethane chains. The expected structure of polyurethane-dispersed diazo black GNN polymer dye was confirmed by FT-IR and UV-vis spectra. The photochromic phenomenon of polyurethane-dispersed diazo-black GNN dyes was investigated. And through the thermogravimetric analysis and differential calorimetry analysis, it is confirmed to be an amorphous structure with good thermal stability. Through the test of its mechanical properties, the results show that the elongation at break is quite high.

Standardized Approach for Monitoring Plasma Cell Disorders

Abstract Multi-color flow cytometry using consensus surface markers (CD138, CD38, CD19, CD45, CD27, CD56, CD81, and CD117), intracellular kappa and lambda, as well as other auxiliary markers is routinely used for the identification and characterization of plasma cells. Here, we describe the development of a modular 10-color plasma cell panel for immunophenotyping of the plasma cell compartment. The panel was developed as an 8-color dried backbone, manufactured in a single test-per-tube, ready to use format. The dried backbone can be supplemented with liquid (drop in) reagents, which provides the flexibility of using intracellular kappa and lambda to examine clonality or using CD38-multi-epitope and/or anti-p63 (VS38c) reagent(s). The single test-per-tube format is ideally suited for MRD applications, where sample size is limited and acquisition of millions of events is needed for data analysis. In addition, the dried reagent tubes have a long shelf life (12 months at 20–25°C vs. 24 hours for liquid cocktails with multiple BV dyes in BSB buffer at 2–8°C). Furthermore, utilization of multiple high-performing polymer dyes in the panel affords high resolution of the relevant cell populations. The dried plasma cell tube(s) were tested on bone marrow samples from healthy and diseased subjects in conjunction with intracellular staining for kappa and lambda. Our results demonstrate that the 10-color plasma cell panel can be used for identification of the plasma cell compartment (based CD38 and CD138 expression), assessment of aberrant marker expression (CD19, CD27, CD81, CD117, CD45, and CD56) for the identification of normal and abnormal plasma cells, and examining clonality in multiple patient samples (Kappa and Lambda).

Novel colored polyurethane nanoparticle for recyclable dyeing polyester fabric

Colored wastewater has to be treated before its discharge, which is a great challenge for the protection of the ecological environment. A novel polymeric dye with nanoparticle morphology has been handily designed to dye polyester fabrics and can be fully recycled to avoid a large number of dyes discharge. It solves the colored wastewater pollution problem in the dyeing process from the source. The colored polyurethane nanoparticles with an average size of 500 nm are prepared via emulsion polymerization. The average content of the colorant monomer on nanoparticle is 2.77%. The colored nanoparticle demonstrates no thermal degradation at 110 °C and no damage under 20 MPa, which means good adaptability for the high-temperature dyeing process. The color depth of dyed polyester fabric can be easily adjusted by changing the concentration of colored nanoparticles in dyebath. The colored nanoparticles in the residual dyebath can be collected by extraction filtration leading to the concentration decreases from 11 mg mL−1 to 0.000025 mg mL−1 after filtered. Both the colored polyurethane nanoparticles and filtered water are fully reused for the next dyeing process to achieve the purpose of avoiding water consumption and residue dyes discharged. This work can promote the development of green and clean dyeing processes in the textile industry.

Ultrasensitive determination of mercury ions using a glassy carbon electrode modified with nanocomposites consisting of conductive polymer and amino-functionalized graphene quantum dots.

A one-pot method based on cyclic voltammetric scan was used to fabricate a glassy carbon electrode modified with nanocomposites consisting of poly(thionine) and amino-functionalized graphene quantum dots (afGQDs). Under near-neutral conditions, the dye polymer was effectively oxidized by hydroxyl radicals (·OH) that were derived from the copper-catalyzed Fenton-like reaction, and the cathodic peak current on the modified electrode greatly increased. The reaction of Cu2+ with thiourea (TU) and the generation of a complex, CuTU2+, led to the decrease of Cu2+/Cu+ species, which inhibited the Fenton-like reaction and reduced the electrochemical response change. Due to a displacement reaction, the addition of Hg2+ into the H2O2-Cu2+-TU system resulted in the release of cuprous ions that benefited the Fenton-like reaction. Under the following optimal conditions: 6mgmL-1 afGQDs and the 25-cycle potential cycling for the fabrication of the modified electrode, pH 6.5, and the [Formula: see text] ratio of 1.0, the increasing extent of the cathodic peak current exhibited a good linear response to the logarithm of the Hg2+ concentration in the range of 1pM-1μM with a detection limit of 0.6pM. Mercury ions in a water sample were determined with good recovery, ranging from 97 to 103%. The investigation on the uptake of Hg2+ into human vascular endothelial cells, HUVEC, shows that the cells incubated in the high-concentration glucose medium absorbed more mercury ions than HUVEC incubated in the normal medium. As a result, Hg2+ could lead to the greater damage to the former. Graphical abstract.

Application of double click to prepare near-infrared absorbing dye for photo-thermal tuning of cholesteric liquid crystal

Cholesteric liquid crystal (CLC) exhibits selective reflection, making it a great application in the field of light control. Here, a near-infrared light (NIR) was used to drive the self-organizing spiral superstructure of the cholesteric liquid crystal to adjust the reflection notch. The polymer dye M2 with near-infrared absorption properties was synthesized by thiol-ene click polymerization and [2 + 2] click reaction; and has good solubility in the CLC system. M2 absorbs near-infrared light to increase the temperature of the system and the temperature-sensitive chiral dopant CD can realize the photothermal tuning of CLC system by the spiral twisting force of CLC with the change of temperature. The use of near-infrared light is beneficial compared to ultraviolet (UV) and visible light because of its invisibility, high penetration and ease of remote control. The entire CLC system has good near-infrared absorption, fast light response and a wide adjustable range.

Synthesis of Polyaniline/Scarlet 3R as a Conductive Polymer.

Polyaniline (PANI) was prepared in the presence of the acidic dye scarlet 3R. Color tuning was performed on PANI through doping–dedoping processes and by changing the solvent used during the optical absorption spectroscopic measurements. The chemical structure of the resulting polymer–dye composite was analyzed using infrared absorption spectroscopy, and it showed the occurrence of secondary doping in m-cresol. The shape of the UV–Vis optical absorption spectra for the composite solution is dependent on the types of organic solvents used during the analysis, which was influenced by the conformation of PANI and the ionic interactions between PANI and scarlet 3R.

Capture and light-induced release of antibiotics by an azo dye polymer

The isomerisation of azo dyes can induce conformational changes which have potential applications in medicine and environmental protection. We developed an agar diffusion assay to test the capture and release of biologically active molecules from an azo electro-optic polymer, Poly (Disperse Red 1 methacrylate) (DR1/PMMA). The assay monitors the growth of bacteria placed in soft agar under a glass coverslip. Antibiotics can then be applied on the coverslip resulting in the clearance of the area under the coverslip due to growth inhibition. This assay demonstrates that DR1/PMMA is able to capture either tetracycline or ampicillin and the relative amount of DR1/PMMA required for capture was determined. Finally, the active antibiotics can be released from DR1/PMMA by exposure to green laser light. Exposure to white light from a torch or to heat does not release the antibiotic.

Scalable Route to Electroactive and Light Active Perylene Diimide Dye Polymer Binder for Lithium-Ion Batteries.

Developing multifunctional polymeric binders is key to the design of energy storage technologies with value-added features. We report that a multigram-scale synthesis of perylene diimide polymer (PPDI), from a single batch via polymer analogous reaction route, yields high molecular weight polymers with suitable thermal stability and minimized solubility in electrolytes, potentially leading to improved binding affinity toward electrode particles. Further, it develops strategies for designing copolymers with virtually any desired composition via a subsequent grafting, leading to purpose-built binders. PPDI dye as both binder and electroactive additive in lithium half-cells using lithium iron phosphate exhibits good electrochemical performance.

Natural ink production and printability studies for smart food packaging

AbstractVersatile smart packages provide information on the freshness of the content and help protect the content from microorganisms. In this sense, in this study both natural antimicrobial properties and pH sensitive natural dyes were obtained from red beet. Inks were prepared and printed using this dye and their suitability for smart packaging was investigated. For this purpose, red beet was cut into small sizes and mixed separately in ethanol and water (1:2) at 200 rpm. The betaine dye was taken up in solvent. These solvents were removed with evaporator and precipitated with centrifugation and dried in a vacuum oven. The chemical structure of the obtained dye was illuminated by Attenuated Total Reflection‐Fourier Transform Infrared Spectroscopy (ATR‐FTIR). The color character was determined by UV spectroscopy. Pink colored natural ink was produced by using ink varnish with carboxymethyl cellulose polymer and solid dye. Screen printing was made with this ink and the color, gloss, and lightfastness characters of prints were examined. Antimicrobial effects of the obtained prints were measured against Staphylococcus aureus and Escherichia coli. Mordanting studies were performed with (KAl[SO4]2.12H2O) and change in color character was measured. The prints produced using the red beet extract have a yellow‐orange color in the basic state; in acid cases it was determined to have a pink‐purple color. In addition, it has been found that the ink prints obtained from red beet have antimicrobial properties against bacteria. Results prove that produced samples have good antimicrobial, pH indicator, and printability properties. This colorant can be used in smart food packaging.

Oligomeric Ruthenium Polypyridyl Dye for Improved Stability of Aqueous Photoelectrochemical Cells

Water-splitting dye-sensitized photoelectrochemical cells rely on molecular sensitizers to harvest light energy and drive the catalytic reactions necessary to generate hydrogen and oxygen from water. The desorption of sensitizer molecules from the semiconductor–aqueous electrolyte interface is a significant barrier to the practical implementation of these cells. To address this problem, we synthesized an oligomeric ruthenium dye ([RuP]n) that has dramatically improved stability as a photosensitizer for TiO2 electrodes over the pH range of interest (4–7.8) for DSPECs. Additionally, the efficiency of photoelectrochemical charge separation is known to depend on the rate of cross-surface hole diffusion between dye molecules. The oligomeric dye ([RuP]n) shows an order of magnitude faster cross-surface hole diffusion than the commonly used monomeric [Ru(bpy)2(4,4-PO3H2)2bpy]2+ (RuP) sensitizer. The enhanced stability of the polymeric dye also enables the use of intensity-modulated photovoltage spectroscopy to measure the recombination rate of photogenerated electrons and holes as a function of electrolyte pH.

The Application of (+)-Catechin and Polydatin as Functional Additives for Biodegradable Polyesters.

Plant polyphenols are a huge group of compounds with a wide spectrum of applications. Substances from this group have been used in polymer materials such as stabilizers, dyes, indicators, fungicides, and bactericides, especially in new generation packaging materials. The aim of this study is to obtain environmentally friendly materials based on the biodegradable aliphatic polyesters, polylactide (PLA) and polyhydroxyalkanoate (PHA), with plant functional additives, (+)-catechin and polydatin. These natural polyphenols (polydatin and (+)-catechin) have not been used so far in polymer materials (especially in biodegradable polyesters) as stabilizers, dyes, and indicators of aging. The application of polydatin and (+)-catechin as multifunctional additives for biodegradable polymers is a scientific novelty. This paper presents the following analyses of polyester materials: SEM microscopy, wide angle x-ray diffraction, mechanical properties, thermal analysis, surface free energy analysis, and determination of change of color after controlled UV exposure, thermal oxidation and weathering. Both PLA and PHA polyesters were characterized by higher resistance to oxidation and greater resistance to degradation under the influence of UV radiation. In addition, (+)-catechin was used simultaneously as a dye and an indicator of the aging time of polymeric materials. In contrast, polydatin did not dye polymers, but was a very good indicator of their lifetime, changing color under the influence of various external factors. Both polyphenols can be successfully used as natural additives for pro-ecological polyesters.

Tunable polymer dye laser pumped by two 513 nm diodes

We demonstrate a tunable solid-state polymer dye laser with quasi-longitudinal pumping by two green (λ = 513 nm) laser diodes. Tuning curves with a maximum efficiency of 13% were attained, using a plate of crystalline quartz (Lyot filter) for wavelength selection. In a three-mirror cavity with partial compensation of astigmatism, the total tuning range was 62 nm (from 545 nm to 607 nm) for pyrromethene dyes: PM567, PM580 and PM597. The best results were achieved with active elements based on Pyrromethene 580 laser dye in a mixture of polyvinyl butyral or a copolymer of butylmethacrylate and methacrylic acid (ratio 9:1) with the addition of 30% dibutylsebacinate as a plasticizer.

Cu2+ sensing via noncovalent complexes of fluorescent whitening agents and imidazole‐based polymeric dye transfer inhibitors

ABSTRACTFluorescent whitening agents (FWAs) and polymeric dye transfer inhibitors (DTIs) are widely used in detergent formulations to combat garment yellowing, fading, and discoloration. We report a new application for these inexpensive, mass‐produced, laundry additives as sensitive fluorescence “turn‐off” sensors for Cu2+. We show that Cu2+‐sensitive FWA–DTI complexes form spontaneously when aqueous solutions of FWA and imidazole‐based DTI are mixed. We also show that the imidazole groups present in the resulting fluorescent FWA–DTI complex selectively bind Cu2+, a potent fluorescence quencher, to form nonfluorescent FWA–DTI‐Cu2+ complexes. Our Cu2+‐sensing FWA–DTI complexes are completely water‐soluble and have a Cu2+ detection limit of ~ 0.14 μM in water. Our simple approach not only converts the Cu2+‐insensitive FWAs into sensitive fluorescent probes for the metal ion but also significantly enhances the brightness of triazinylaminostilbene FWAs. The present study provides a facile, synthesis‐free strategy for producing inexpensive fluorescent sensors for Cu2+. © 2020 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020, 137, 48915.

Secondary electro-optic response induced by VOD875S dye in polymer stabilised liquid crystals

ABSTRACT Polymer stabilised liquid crystal, which has the scattering state and transparent state, is widely used in tunable optic devices. Here, we demonstrate a polymer stabilised liquid crystal device with secondary electro-optic response phenomenon. Doped VOD875S dye into the normal polymer stabilised liquid crystal, the transmittance of the scattering and transparent states is reduced; moreover, the transparent region can be extended beyond the electrode and the transmittance is increased again when the operating voltage is larger than a critical value. The effects of dye concentration, polyimide (PI) layer and surfactant concentration on the secondary electro-optic response phenomenon of PSLC film were studied. It was found that high dye concentration, no PI layer and high surfactant concentration can effectively reduce the critical voltage of the secondary electro-optic response phenomenon. The secondary electro-optic response phenomenon can be used in some smart devices.

The synthesis of polymeric dyes based on waterborne polyurethane: a reaction kinetics study using UV absorption spectroscopy

The preparation of waterborne polyurethane based polymeric dyes (DWPU) with anthraquinone chromophores was monitored by using UV absorption spectroscopy for the first time.

Logic-signal-based multiplex detection of MiRNAs with high tension hybridization and multiple signal amplification.

MicroRNAs (miRNAs) are crucial regulators of gene expression. The abnormal expression of miRNA is often closely related to many diseases. However, the accurate clinical profiling of miRNA expression remains a great challenge due to the high similarity and wide variety of miRNA sequence structures. Here, we report a highly specific and sensitive multiplex miRNA detection scheme with high tension hybridization and dual signal amplification based on the recyclable autocatalytic DNAzyme and a light harvesting conjugated polymer. Multiple signals can be read out simultaneously by single excitation through the efficient multiple fluorescence resonance energy transfer (FRET) between the conjugated polymer and different small molecule dyes. In addition, different types of logic gates can also be operated by observing the emission intensities of the labeling dyes with miRNAs as inputs, thus giving rise to a new way for the specific detection of certain miRNAs according to the logic signals. Furthermore, we successfully applied the strategy for multiple miRNA detection in cell lysates and the results agree well with those of qRT-PCR. Thus, we believe that this platform holds great potential for miRNA detection in biological samples.

A review on biological activities of Schiff base ligand and their metal complexes

Schiff bases and their metal complexes are wide range of biological applications and are synthesized from the condensation reaction of amino compounds with carbonyl compounds. Schiff base and their metal complexes have a wide variety of applications in food and dye industry, agrochemical, polymer, catalysis, analytical chemistry, antifertility, antiinflammatory activity, antiradical activity, and biological system as enzymatic agents. Several have reviewed them of their antimicrobial, antibacterial, antifungal, antitumor, and cytotoxic activities. This review summarized the most promising biological activities of Schiff bases and their metal complexes

Synthesis and application of a phosphorus-containing waterborne polyurethane based polymeric dye with excellent flame retardancy

To endow waterborne polyurethane (WPU) with bright color and improve the flame retardancy, a series of flame-retardant and colorful WPU (DOWPU) was synthesized by incorporating anthraquinone chromophore (DV26) and phosphorus-containing flame-retardant (OP550) into the skeleton simultaneously. The migration property, thermal performance and flame retardancy of DOWPU were systematically characterized by a series of experiments, showing that DOWPU was endowed with bright color and satisfactory flame retardancy. Interestingly, the synergistic effect between DV26 and OP550 made the char yield of DOWPU as high as 25.14 %, which increased the limiting oxygen index by 8.1 %. Furthermore, the migration percentage of DOWPU was only 3.9 %, which was attributed to the strong covalent bonding force between DV26 and polymer chains. Additionally, we coated DOWPU on the polyester fabrics to prove the practicality. The coated fabrics not only had bright colors, but also exhibited excellent color fastness and flame retardancy.