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A series of naphthalimide dyes (TRNATR, MOTNAMOT, MPNAMP, TYNATY, PNAP and IZNAIZ) were designed and synthesized by altering the side chains of the naphthalimide. Without the need for ER-targeting groups, the first five dyes were found to specifically target the ER, likely due to their well-suited lipophilic properties. Furthermore, TRNATR and TYNATY were proven effective for studying ER stress, showing promise in tracking ER autophagy in living cells triggered by tunicamycin and nutritional starvation. [ABSTRACT FROM AUTHOR]

Taking advantage of the excellent host–guest complexation ability between an auxochrome (adamantane group) and CB[7], the fluorescence emission performance of dyes in water was effectively improved with the addition of two equivalents of CB[7], which provided an efficient method for increasing fluorescence intensity in aqueous environments. Furthermore, these dyes with the host were successfully used in cell imaging. [ABSTRACT FROM AUTHOR]

Structurally symmetric dyes using functionalized fluorenes and benzotriazole as the main building moieties have been synthesized and found to exhibit efficient dual-state emission (DSE) and interesting two-wavelength or dual amplified spontaneous emission (dual-ASE) behaviors in the solution phase, which may benefit the development of organic gain materials with dual-wavelength amplification. [ABSTRACT FROM AUTHOR]

Among other photovoltaic techniques including perovskite solar cells and organic solar cells, dye-sensitized solar cells (DSSCs) are considered to be a potential alternative to conventional silicon solar cells. Porphyrins are promising dyes with the properties of easy modification and superior light-harvesting capability. However, porphyrin dyes still suffer from a number of unfavorable aspects, which need to be addressed in order to improve the photovoltaic performance. This feature article briefly summarizes the recent progress in improving the Voc and Jsc of porphyrin-based DSSCs in terms of molecular engineering by modifying the porphyrin macrocycle, donor and acceptor moieties of the porphyrin dyes, coadsorption of the porphrin dyes with bulky coadsorbents like chenodeoxycholic acid (CDCA), and cosensitization of the porphyrin dyes with metal-free organic dyes. Notably, concerted companion (CC) dyes are described in detail, which have been constructed by linking a porphyrin dye subunit and a metal-free organic dye subunit with flexible alkoxy chains to achieve panchromatic absorption and concerted enhancement of Voc and Jsc. In one sentence, this article is expected to provide further insights into the development of high performance DSSCs through the design and syntheses of efficient porphyrin dyes and CC dyes in combination with device optimization to achieve simultaneously elevated Voc and Jsc, which may inspire and promote further progress in the commercialization of the DSSCs. [ABSTRACT FROM AUTHOR]

Dual thermo- and light-responsive water-soluble copolymers that respond to exclusively non-invasive triggers are obtained by functionalising poly(N,N-dimethylacrylamide) with arylazopyrazole side chains. The light-induced E–Z (trans–Z) photo isomerisation of these dyes provides an exceptionally effective photo-switch, which can reversibly shift the LCST-type phase transition temperatures by almost 25 K. [ABSTRACT FROM AUTHOR]

Cyanation has attracted considerable attention in organic synthesis because nitriles are key structural motifs in numerous important dyes, agrochemicals, natural products and drug molecules. As the fourth generation of cyanating reagents, isocyanides occupy a prominent place in the synthesis of nitriles due to their favorable stability, easy operability and high reactivity. In recent years, three types of cyanation with isocyanides have been established: the cleavage of the C–NC bond of tertiary alkyl isocyanides (Type I), the rearrangement of aryl isocyanides with azides (Type II), and the reductive cyanation of ketones with α-acidic isocyanides (Type III). This review focuses on advances in cyanation with isocyanides with an emphasis on reaction scope, limitations and mechanisms, which could reveal their remarkable value and superiority for accessing various nitriles. In addition, the future development prospects of this specific field are also introduced. We believe that this feature article will serve as a comprehensive tool to navigate cyanation with isocyanides across the vast area of synthetic chemistry. [ABSTRACT FROM AUTHOR]

Development of two-dimensional materials and exploration of their functionalities are significant challenges due to their potential. In this study, we successfully fabricated a supramolecular nanosheet composed of amphiphilic Rose Bengal dyes in an aqueous medium. Furthermore, we elucidated a distinct change in the photosensitisation mechanism induced by nanosheet formation. [ABSTRACT FROM AUTHOR]

Here, we present a new route to dyes of the BODIPY family. We first built up a N-Boc-protected dipyrromethene scaffold via an aminopalladation cascade. Subsequentially, the pyrrole moiety was deprotected and the BF2 unit inserted. Depending on the terminating reaction, BODIPYs with either aryl or alkynyl moieties were accessible. [ABSTRACT FROM AUTHOR]

Traditional water-soluble organic macrocyclic receptors generally lack photofunctionality, thus monitoring the drug delivery and the phototheranostic applications of these host–guest macrocyclic systems has been greatly restricted. To address this issue, incorporating π-conjugated dye chromophores as building blocks into macrocyclic molecules is a straightforward and promising strategy. This approach not only imparts intrinsic optical features to the macrocycles themselves but also enhances the host–guest binding ability due to the large planar structures of the dyes. In this feature article, we focus on recent advances in water-soluble macrocyclic compounds based on organic dye chromophores, such as naphthalimide (NDI), perylene diimides (PDI), azobenzene (azo), tetraphenylethylene (TPE) and anthracene, and provide an overview of their various applications including molecular recognition, drug release, biological imaging, photothermal therapy, etc. We hope that this article could be helpful and instructive for the design of water-soluble dye-based macrocycles and the further development of their biomedical applications, particularly in combination with drug therapy and phototheranostics. [ABSTRACT FROM AUTHOR]

Removal of dyes from various industrial effluents is a great challenge, and cost-effective methods and materials with high dye removal efficacy are in high demand. Adsorption, nanofiltration and photocatalytic degradation are three major techniques that have been investigated for dye removal. PIMs are promising materials for use in these three methods based on their attributes, such as microporosity, solution processibility, high chemical stability and tunability through facile synthesis and easy postmodification. Although the number of reports on dye removal employing PIMs are limited, some of the materials have been shown to exhibit good dye separation properties, which are comparable to those of the state-of-the-art material activated carbon. In this highlight, we make an account of progress in PIMs and PIM-based composite materials in different dye removal processes over the last decade. Furthermore, we discuss the existing challenges of PIM-based materials and aim to analyze the key parameters for improving their dye removal properties. [ABSTRACT FROM AUTHOR]

Layer-by-layer assembly of strong polyelectrolytes was successfully implemented on hydrophobic particles in degassed saline water thanks to de-gassing-reduced hydrophobic interactions and salinity-reduced hydration. The resulting polyelectrolyte multilayer coated particles were readily converted to hydrophobic yolk/hydrophilic shell particles for the removal of organic dyes from water via both electrostatic and hydrophobic interactions. [ABSTRACT FROM AUTHOR]

Anionic hydrogen bonded frameworks were synthesised from di or tetra-amidinium hydrogen bond donor components and a charge "mis-matched" tecton possessing a 5− charge but only four hydrogen bond accepting groups. The net negative charge on the framework skeletons necessitates the presence of a cation in the framework channel. In one of the frameworks, the initially incorporated organic cation was rapidly displaced by smaller inorganic cations, or the cationic dye methylene blue. This facilitated the effective and selective removal of this dye from water. [ABSTRACT FROM AUTHOR]

Local pH changes were produced upon electrochemical reactions. Cyclic application of reductive and oxidative potentials resulted in the formation of pH waves in the form of distinct solution layers. Multiple layers with basic and acidic pH values were visualized with a fluorescence confocal microscope following fluorescence of pH-dependent dyes. [ABSTRACT FROM AUTHOR]

We report J-aggregates of a boron dipyrromethene derivative (BDP-Nit) as an H2S-activatable nano-photosensitizer. The closely packed BDP-Nit in J-aggregates exhibits high selectivity to H2S over biothiols to produce an active photosensitizer. [ABSTRACT FROM AUTHOR]

2-Thiobarbituric acid-functionalized naphthalene dye selectively self-assembles into crystalline fibers to show material properties that are different from those of a previously reported oxo-barbituric acid derivative affording curved supramolecular polymers via the formation of hydrogen-bonded rosettes. Detailed studies using 1H-NMR, DFT calculation and X-ray diffraction revealed that the crystalline fiber is formed through a tape-like hydrogen-bonding pattern due to the weaker hydrogen-bond-acceptor ability of the thiocarbonyl group. [ABSTRACT FROM AUTHOR]

The kinetic assembly pathways of a newly synthesized amphiphilic aza-BODIPY dye 1 were tuned by using H2O as a co-solvent in MeOH. Accordingly, the biphasic aggregation pathways resulting in kinetically-trapped and thermodynamically stable aggregates of 1 were established and the multiple cyclic seeded living supramolecular polymerization of this dye was realized. [ABSTRACT FROM AUTHOR]

BINOL moieties of different electronic demand are useful blocks for enabling the photo-production and modulation of triplet excited states in readily-accesible BINOL-based O-BODIPY dyes from standard F-BODIPY precursors. The rapid and rational development of smarter triplet-enabling BODIPY dyes on the basis of this strategy (e.g., TADF biomarker 4a or room temperature phosphor 4g) paves the way for advancing photonic applications based on organic triplet photosensitizers. [ABSTRACT FROM AUTHOR]

Fluorene-based analogues of fluorescein, rhodol, and rhodamine exhibit absorption and fluorescence beyond 800–900 nm in water, 300–400 nm red-shifted compared to the original oxygen-bridged xanthene dyes, giving potential access to low molecular weight fluorescent markers for the second biological window (NIR-II, ca. 1000–1350 nm). [ABSTRACT FROM AUTHOR]

The microfluidic production of Janus/Hecate polymer microfibers with well-defined interfaces from miscible phases is reported. The process offers tunability of the width and composition of each part of the fibers by controlling the flow rate and nature of the monomers in a single step. The enhanced performances of the fibers are outlined for the simultaneous removal of dyes of opposite charges using amphoteric Janus fibers. [ABSTRACT FROM AUTHOR]

Here, we report the installation of 1,8-naphthalimide dyes in live cell imaging of plants. We developed a series of 1,8-naphthalimide-based probes that illuminate different subcellular compartments by altering their spectral characteristics. Simple infiltration of the probes into leaves rapidly visualized the structure of chloroplasts or the vacuole. We further demonstrated that these probes are applicable to monitor the organelle behaviors in an autophagy pathway. [ABSTRACT FROM AUTHOR]

New amphiphilic carbazole-based dyes assemble in water into deep-blue-emitting, highly fluorescent helical aggregates as observed by transmission electron microscopy and atomic force microscopy. Single crystal X-ray diffraction and NMR spectroscopy reveal that self-complementary, antiparallel H-bonding and π–π stacking interactions are the driving forces for the formation of these dye aggregates. [ABSTRACT FROM AUTHOR]

The host–guest binding between a chiral macrocycle and an achiral dye could suppress the twisted intramolecular charge transfer (TICT) process, leading to enhanced emission and bright circularly polarized luminescence (CPL) from the originally achiral TICT-dye. [ABSTRACT FROM AUTHOR]

A supramolecular dye-capture system comprising anionic amidosquaraine guest and macrocyclic tetralactam host exhibits nanomolar affinity and "turn on" visible fluorescence. Utility is demonstrated with a new fluorescent assay for liposome leakage induced by the biomedically important enzyme phospholipase A2. [ABSTRACT FROM AUTHOR]

Protein misfolding and aggregation processes involve local polarity and viscosity fluctuation. Herein we modulated the polarity and viscosity sensitivities of merocyanine dyes to detect protein aggregation. We demonstrated how structural modulation balanced these two fluorescence sensitivities and affected the detection of misfolded and aggregated proteins. [ABSTRACT FROM AUTHOR]

We herein developed a novel method for alkaline phosphatase (ALP) assay based on the target-induced transcription of a light-up RNA aptamer, consequently producing a highly enhanced fluorescence signal upon specifically binding to the corresponding dye. Using this strategy, we successfully determined the ALP activity down to 0.018 U L−1 (dynamic linear range of 0.04–4 U L−1) with excellent selectivity. [ABSTRACT FROM AUTHOR]

A tri-β-cyclodextrin-armed host compound is synthesized to construct layered supramolecular network co-assembly with a doubly azobenzene-decorated polyoxometalate cluster through host–guest interaction. The porous hybrid assembly displays automatic degradation of selective dyes and the acceleration of the partner dye in both water and dichloromethane in the air. [ABSTRACT FROM AUTHOR]

Light-up DNA aptamers are promising label-free signal-transducers for biosensing applications due to their high chemical stability and low synthetic cost. Herein, we demonstrate that a dapoxyl DNA aptamer DAP-10–42 can be converted into a sensor generating a fluorescence signal at different wavelengths in the range of 500–660 nm depending on the dye that is present. This results from the discovered promiscuity of DAP-10–42 in binding fluorogenic dyes including arylmethane dyes. We have designed a split DAP-10–42 aptasensor for the detection of a katG gene fragment from Mycobacterium tuberculosis with a point mutation causing isoniazid resistance. Efficient interrogation of the gene fragment after nucleic acid sequence-based amplification (NASBA) is achieved directly in a protein-containing NASBA sample. This report lays a foundation for the application of the DAP-10–42 aptamer as a versatile sensing platform. [ABSTRACT FROM AUTHOR]

Two new dyes consisting of an aromatic amine donor and dansyl acceptor were synthesized, where the intramolecular donor and acceptor are connected by Diels–Alder dynamic covalent bonds. These new dyes display a switchable fluorescence resonance energy transfer through reversible formation and cleavage of Diels–Alder bonds. Single crystal X-ray diffraction revealed that Diels–Alder bonds are longer and weaker than normal single bonds. Dynamic covalent properties enable the mutual conversion of the two dyes by maleimide exchanges, where a new higher energy transfer efficiency system can be constructed. [ABSTRACT FROM AUTHOR]

Three new ruthenium(II) complexes containing an N-heterocyclic carbene (NHC) ligand (RuNHC) have been successfully synthesized and proved to be efficient near-infrared (NIR) ECL (electrogenerated chemiluminescence) luminophores. In addition to the advantages of the lower-charge main motif (+1), the much lower oxidation potentials, and the longer metal to ligand charge transfer (MLCT) absorption bands, most importantly, these RuNHC complexes show higher, or at least comparable, ECL efficiency compared with Ru(bpy)32+ under the same experimental conditions; this demonstrates their great potential for applications in the NIR ECL imaging field in the future. [ABSTRACT FROM AUTHOR]

Herein, we introduce the concept of hydrophobic domain flexibility to control the morphology of aqueous assemblies. To this end, we examined two amphiphilic 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes that differ in the flexibility of the hydrophobic residue (tetradecyl vs. cholesterol). This minor structural difference significantly affects the self-assembly behaviour (spherical vs. two-dimensional sheets) by overruling the packing parameters. [ABSTRACT FROM AUTHOR]

A BODIPY dye functionalized with uracil-ethynyl groups at the 2,6-positions supramolecularly polymerized into J-aggregates directed by intermolecular H-bonds and featured intense absorption and resonant fluorescence. The alignment of J-aggregated chromophores in a thin film was achieved by a rubbing method and polarized photoluminescence with a dichroic ratio up to 14.3 was obtained. [ABSTRACT FROM AUTHOR]

The benzocoumarin dyes fluoresce negligibly in aqueous media but very strongly in cells, whereas representative conventional dyes display contrasting behaviour; the distinct emission behaviour of the fluorophores in organic solutions, in aqueous media, and in cell convinces the uniqueness of the cellular environment. The in cellulo superbright benzocoumarins also reveal an environment-insensitive emission behaviour, which is required for the reliable analysis via ratiometric imaging. [ABSTRACT FROM AUTHOR]

A series of water-soluble helicene dyes generating intense electrochemiluminescence (ECL) signal in physiological conditions is reported. Those species were prepared using diaza [4] and [6]helicenes as structural cores modified with sulfonate groups in various positions. Such groups improve their water solubility and can induce a red-shifted emission. Efficient ECL up to the near-infrared is achieved in water, demonstrating a viable strategy for the design of new near-infrared ECL dyes for bioassays and microscopy. [ABSTRACT FROM AUTHOR]

As environmental problems increase, there is an urgent demand for new eco-friendly materials. Natural rubber latex (NRL) is a natural material extracted from rubber trees. But its dyeing process with chemical dyes might result in contamination and environmental degradation. Here, NRL is composited with a photonic crystal (PhC) structure by spin coating for the first time. The polymethyl methacrylate (PMMA) photonic nanostructure has been embedded into NRL to give it colors and provide it with optical functionalities. Colors of the composite could be designed and controlled by the sizes of the nanocolloids from 180 nm to 295 nm. The colors have strong stability under external stretching. The 3D natural rubber latex photonic crystal (NRLPC) is used as a responsive material to detect volatile organic compounds (VOCs) including formaldehyde, acetone, toluene, xylene and styrene. With its visual color appearance, biocompatibility and flexibility, NRLPC has promising potential in various sensing applications. [ABSTRACT FROM AUTHOR]

A tetralactam macrocycle acts as a novel supramolecular adjuvant to capture a released resorufin dye and create a higher contrasting yellow/blue color change for enhanced naked eye interpretation of a colorimetric indicator assay. [ABSTRACT FROM AUTHOR]

In this article, we report the synthesis and use of iminosydnone-based profluorophores as bioorthogonal cleavable linkers for imaging applications. These linkers react with cycloalkynes via subsequent [3+2] cycloaddition and retro Diels–Alder reactions, allowing simultaneous release of two dyes in biological media. [ABSTRACT FROM AUTHOR]

Four water-soluble macrocycles were chosen to explore the photodecomposition behaviours of quaternized 9-alkoxy-substituted anthracene (AnQA). Significantly, a highly charged macrocyclic skeleton leads to extremely close packing among the anthryl rings, providing a favourable hydrophobic environment for singlet oxygen, leading to rapid oxidation to produce the photoproducts under sunlight irradiation. [ABSTRACT FROM AUTHOR]

Methods to red-shift fluorophores have garnered considerable interest due to the broad utility of low energy light. The incorporation of silicon into xanthene and coumarin scaffolds has resulted in an array of visible and near-infrared fluorophores. Here, we extend this approach to polymethine dyes, another popular fluorophore class, performing experimental and computational analyses. We found that when oxygen was replaced with SiMe2, bathochromic shifts of up to 121 nm and fluorophores with emission above 900 nm were achieved. [ABSTRACT FROM AUTHOR]

We demonstrate the possibility to detect selectively the two single enantiomers of a model [Ru(bpy)3]2+-based dye by circularly polarized-electrochemiluminescence (CP-ECL). This new aspect of the ECL emission combines the chiral information intrinsic to CPL methods with an electrogeneration of the excited state. Thus, it opens the possibility to perform ECL-based bioassays or microscopy with efficient chiral dyes. [ABSTRACT FROM AUTHOR]

New easily functionalisable and highly fluorescent BOPAHY chromophores are synthesised via a one-pot two-step reaction starting from commercially available pyrrole-2-carbaldehydes and respective acyl hydrazides in the presence of BF3·OEt2. Most importantly, all BOPAHY dyes show excellent photophysical properties with quantum yields up to 0.92. Steady-state spectroscopy and quantum chemical calculations provide a first insight into these promising properties. [ABSTRACT FROM AUTHOR]

A novel spiro-fused terrylene dimer (SDT) was designed and synthesized by a dissymmetric spiro-fusion strategy. The spiro-conjugation effect caused a distinct red-shift and enhancement of the absorption spectrum. Two chiral enantiomers of SDT have been absolutely resolved and identified in combination with theoretical calculations. Circularly polarized luminescence (CPL) measurement revealed its potential as a near-infrared chiral luminescent material. [ABSTRACT FROM AUTHOR]

A new synthetic methodology based on the self-condensation of 1,2,3-benzodithiazolyl diradicals (Herz radicals) produces unprecedented 5-6-6-6-5 and 5-6-7-6-5 pentacyclic sulfur-nitrogen near-IR dyes featuring up to five multiple long-lived and differently coloured redox-states. [ABSTRACT FROM AUTHOR]

Covalent organic framework (COF) membranes are attractive candidates for molecular separation. Herein, COF–LZU1 composite membranes were prepared by a stoichiometric spraying layer-by-layer self-assembly method for the first time. The membranes displayed a high rejection (>90%) and permeance (>400 L m−2 h−1 MPa−1, 50–880% higher than traditional membranes) for dyes (Mw 350–800). [ABSTRACT FROM AUTHOR]

The metathesis of dialkylarylvinylsilane, which has not been accomplished to date, is achieved using dialkylaryl-iso-propenylsilane as a substrate. In addition, we discovered that the reason why the metathesis of a ruthenium carbene complex and dialkylarylvinylsilane is difficult is the formation of a carbide complex. [ABSTRACT FROM AUTHOR]

Single-crystal-to-single-crystal (SC–SC) structural self-evolution has been successfully performed on an amino-functionalized MOF material, which has greatly improved the Hg2+ removal performance of the material and implemented dye molecule encapsulation through a dissolution–encapsulation–recrystallization process for the first time. [ABSTRACT FROM AUTHOR]

We have synthesized symmetrical carbocyanine dyes in which two 4-quinolinium rings are joined by a pentamethine bridge that is meso-substituted with H or Cl. Irradiation of the halogenated dye at 830 nm produces hydroxyl radicals that generate DNA direct strand breaks. This represents the first reported example of DNA photocleavage upon single photon excitation of a chromophore at wavelengths above 800 nm. [ABSTRACT FROM AUTHOR]

Indolizine derivatives are obtained by irradiation of 2-benzoyl-N-benzylpyridinium derivatives and dimethyl acetylene dicarboxylate, thus providing a competitive and complementary base- and catalyst-free synthesis. With this method, the first example of a crystallochromic indolizine is presented, whose color in the solid state depends on the out-of-plane torsion of the benzoyl substituent. [ABSTRACT FROM AUTHOR]

Different from traditional "always on" photothermal therapy (PTT) agents, tumor microenvironment responsive agents showed more tumor specificity and lower photo-toxicity to normal tissues. Herein, a photo-stable and reversible pH responsive phenazine dye (PIOH) was synthesized and assembled with liposomes forming nanoparticles (PIOH-NPs), which exhibited a strong NIR absorption in a weak acid environment and were successfully utilized for photoacoustic (PA) imaging-guided photothermal therapy in mice. [ABSTRACT FROM AUTHOR]

A truly ratiometric homogeneous electrochemical biosensor has been developed for sensitive miRNA detection based on the unique diffusion/intercalation properties of electroactive dyes without the need for electrode modification or materials preparation. [ABSTRACT FROM AUTHOR]

Stomatocyte-like hollow polydopamine nanoparticles (SHPNs) are synthesized for rapid removal of water-soluble dyes from water. They demonstrate an exceptionally high adsorption capacity of 2896 mg g−1 for methylene blue (MB) and can rapidly sequester MB from water within 20 seconds. Moreover, SHPNs can be regenerated easily using a mild washing procedure. [ABSTRACT FROM AUTHOR]