Naphthalimide Dyes Research Articles

Investigation of using amine and acetylamine functional units on naphthalimide dyes for photovoltaic devices

Purpose The purpose of this paper is to introduce four new organic dyes based on naphthalimide for dye-sensitized solar cells (DSSCs). Design/methodology/approach Four new dyes based on naphthalimide with substitutions of amine and acetylamine in position C4 were designed in conjugation with substituted carbazole as donor–acceptor (D-A) architecture. The absorption and emission characteristics of the prepared dyes were evaluated in H2O, DMF and their mixture (DMF:H2O = 1:1). The feasibility of electron transfer in the DSSCs structure and energy levels were evaluated using electrochemical and density functional theory, which confirm the use of dyes in the DSSCs structure. The DSSCs were prepared using an individual strategy and their optical properties were investigated under the light of AM 1.5. Findings The prepared dyes exhibit orange color with strong emission at λem = 530–570 nm due to charge transfer with a positive solvatochromic effect. The efficiency of DSSCs based on Dye1-4 1 is: 3.69%, 3.71%, 4.69% and 4.76%. Therefore, the power efficiency increases by about 29 % in the presence of acetylamine group. Practical implications The design of new structures of organic dyes should be accompanied by the development of optical and electrical properties. In other words, in addition to the continuous production of electrons, efficient dyes must also be resistant to light to increase the life of the device. Social implications Organic dyes play a key role in the production of electrons in the DSSCs structure. The engineering of these structures and the introduction of widely used but low cost types can play an important role in the development of clean energy production. Originality/value The application of organic dyes based on naphthalimide was evaluated in the DSSCs structure and its photovoltaic properties were investigated.

Synthesis and photophysical properties of water soluble phosphonic acid functionalized naphthalimide dye

Synthesis and photophysical properties of water soluble phosphonic acid functionalized naphthalimide dye

A naphthalimide-based fluorescent platform for endoplasmic reticulum targeted imaging.

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.

A dual-responsive fluorescent probe based on cyanine and naphthalimide units for detecting HClO and H2S in living cells

Hypochlorous acid (HClO) and hydrogen sulfide (H2S) play very important roles in both physiological and pathological processes, however, the methods for simultaneously detecting HClO and H2S were rarely reported. Here, a dual–responsive fluorescent probe (CyNa-N3) based on cyanine and naphthalimide dyes was synthesized and investigated. The fluorescence probe showed better sensitivity, high selectivity response to HClO and H2S by red emission and green emission bands, and the limits of detection were 0.17 µM and 0.15 µM respectively. MS (Mass Spectrum) and 1H NMR (Nuclear Magnetic Resonance) confirmed the sensing mechanism of CyNa-N3 detected HClO and H2S, the calculation of density functional theory (DFT) further explained the internal mechanism of spectral change of CyNa-N3. Moreover, CyNa-N3 was successfully applied to image HClO and H2S in living cells, which is beneficial for more efficient application in biological imaging.

White light generation by regulating hydrogen bond-sensitive ESPT of naphthalimide dyes

White light emitting systems of pure organic materials have attracted extensive research interest due to their better compatibility and functional scalability. The reported organic white light materials are mainly based on the multi-channel emission regulation of the compound itself or the mixing of multicolor luminescence materials, but studies on the dependence between multicolor luminescence and the external environment are lacking, which limits the application of these materials in areas such as identification and sensing. This paper reports that the 4- or 3‑hydroxyl-substituted naphthalimides NapH1 and NapH2 form intermolecular hydrogen bonds with adjacent molecules in the environment, and undergo excited-state intermolecular proton transfer under irradiation, resulting in blue-yellow or blue-red dual fluorescence emission, respectively. Since the two compounds have different two-color luminescence channels and the two-color intensity ratio is affected by the environment, and the intermolecular hydrogen bond is determined by the hydrogen bond receptor, polarity, and temperature in the environment, the full spectrum from blue to red light and white light emission can be obtained by adjusting the mixing ratio of the two dyes and the solvent polarity and the ambient temperature. This environmentally sensitive white emission is used to detect the alkalinity of different papers, and the dyed paper can be used as a test strip for acid-base vapor detection.

Visible light induced regioselective C-3 thiocyanation of imidazoheterocycles through naphthalimide dye based photoredox catalysis.

A visible light induced C-3 thiocyanation of imidazo[1,2-a]pyridines by using a naphthalimide based photoredox catalyst has been reported. Tolerance of electron withdrawing and donating groups at different positions of the imidazo[1,2-a]pyridine ring led to a wide substrate accessibility of this method. This methodology is further reproducible with other heterocycles like benzo[d]imidazo[2,1-b]thiazoles, indoles, azaindoles, and anilines.

Inverted and Amplified CP-EL Behavior Promoted by AIE-Active Chiral Co-Assembled Helical Nanofibers.

It is well-known that high-performance circularly polarized organic light-emitting diodes (CP-OLEDs) remain a formidable challenge to the future application of circularly polarized luminescent (CPL)-active materials. Herein, the design of a pair of AIE-active chiral enantiomers (L/D-HP) is described to construct chiral co-assemblies with an achiral naphthalimide dye (NTi). The resulting co-assemblies emit an inverted CPL signal compared with that from the L/D-HP enantiomers. After thermal annealing at 120°C, the inverted CPL signal of this kind of L/D-HP-NTi with a 1:1 molar ratio shows regular and ordered helical nanofibers arranged through intermolecularly ordered layered packing and is accompanied with a further amplified effect (|gem |= 0.032, λem = 535nm). Significantly, non-doped CP-OLEDs based on a device emitting layer (EML) of L/D-HP-NTi exhibits a low turn-on voltage (Von ) of 4.7V, a high maximum brightness (Lmax ) of 2001cdm-2 , and moderate maximum external quantum efficiency (EQEmax ) of 2.3%, as well as excellent circularly polarized electroluminescence (CP-EL) (|gEL |= 0.023, λem = 533nm).

An effective fluorescent probe for detection of phosgene based on naphthalimide dyes in liquid and gaseous phases

A fluorescent probe was developed for the detection of phosgene based on 1,8-naphthalimide, of which o-diaminobenzene was used as the recognition moiety. The probe does not fluoresce due to nonradiative decay. The probe reacts rapidly with phosgene via an intramolecular cyclization reaction, which induces large fluorescence due to increased rigidity in the resulting molecule and a low detection limit (0.23 nM). This probe has excellent selectivity for phosgene against competing interference analytes and, in the form of probe-loaded test paper, is an extremely sensitive method for phosgene sensing in the gas phase below 1 ppm concentrations.

Golgi-Targeting Fluorescent Probe for Monitoring CO-Releasing Molecule-3 In Vitro and In Vivo.

CO-releasing molecule-3 (CORM-3), mainly metal carbonyl compounds, is widely used as experimental tools to deliver CO, a biological “gasotransmitter”, in mammalian systems. CORM-3 is also proposed as a potential new antimicrobial agent, which kills bacteria effectively and rapidly in vitro and in animal models. Organelle-targeting therapy, as a highly effective therapeutic strategy with little toxic and side effects, has important research significance and development prospects. Therefore, the development of effective methods for detecting and tracking CORM-3 at the subcellular level has important implications. In this paper, an easily available Golgi-targetable fluorescent probe (Golgi-Nap-CORM-3) was proposed for CORM-3 detection. In the probe Golgi-Nap-CORM-3, the phenyl sulfonamide group was selected as the Golgi-targetable unit, naphthalimide dye was chosen as a fluorophore, and the nitro group was selected as a CORM-3-responsive unit. Golgi-Nap-CORM-3 shows a CORM-3-reponsive increase of fluorescence emission at 520 nm. Using the excellent probe, the change of CORM-3 in HeLa cells, HepG2 cells, and zebrafish is successfully monitored. This study demonstrates very important information for the study of CORM-3 in vivo systems.

Photostable fluorescent probes based on multifunctional group substituted naphthalimide dyes for imaging of lipid droplets in live cells.

We designed and synthesized multifunctional group substituted naphthalimide (MFGNI) dyes by introducing glycine ethyl ester and azetidine on 1,8-naphthalimide. With different azetidine substituents, the emission of the MFGNI dyes was shifted from blue to green. These MFGNI dyes exhibited high photoluminescence quantum yields (61% to 85%) and large Stokes shifts (67 nm). The amides and hydroxyl groups improved the photostability of the MFGNI dyes. Due to the small molecular weight and lipophilic properties, these MFGNI dyes specifically stained lipid droplets in living cells.

Synthesis, biological evaluation and cellular localization study of fluorescent derivatives of Jiyuan Oridonin A

Jiyuan Oridonin A (JOA) is a naturally occurring ent-kaurane diterpenoid that exhibits significant potential in the field of anti-tumor drug development. However, its detailed anti-cancer mechanism of action has not been fully understood. In order to investigate its anticancer mode of action, two series of novel fluorescent derivatives of JOA conjugated with naphthalimide dyes were synthesized, and their antitumor activity against five selected cancer cell lines (MGC-803, SW1990, PC-3, TE-1 and HGC-27) was evaluated. Compared with JOA, the anti-tumor activity of the vast majority of compounds were improved. Among them, B12 exhibited promising anti-proliferative activity against HGC-27 cells with IC50 value of 0.39 ± 0.09 μM. Fluorescence imaging studies demonstrated that probe B12 could enter HGC-27 cells in a dose-dependent and time-dependent manner and was mainly accumulated in mitochondria. Preliminary biological mechanism studies indicated that B12 was able to inhibit cell cloning and migration. Further studies suggested that B12-induced apoptosis was related to the mitochondrial pathway. Overall, our results provide new approaches to explore the molecular mechanism of the natural product JOA, which would contribute to its further development as an antitumor agent.

Full‐Color and White Circularly Polarized Luminescence Promoted by Liquid Crystal Self‐Assembly Containing Chiral Naphthalimide Dyes

AbstractChiral emissive nematic liquid crystals (N*‐LCs) can greatly amplify the circularly polarized luminescence (CPL) signals promoted by a highly regular spiral self‐assembly in the LCs system. Naphthalimide (NI) derivatives have been assigned to be one of the most excellent chromophores for fluorescent materials. In this paper, a novel strategy is first developed to regulate full‐color CPL behavior of N*‐LCs through different chiral NI‐based dyes. Chiral NI‐based dyes are doped into nematic liquid crystals (E7, N‐LCs) to form N*‐LCs as CPL‐active liquid crystal materials. Most interestingly, this kind of N*‐LCs could emit standard white CPL signals (CIE coordinates: (0.31, 0.33)) by choosing the blue‐red match of two chiral NI‐based dyes at the appropriate ratio.

Evaluation of the mechanical properties and blood compatibility of Polycarbonate Urethane and fluorescent self-colored Polycarbonate Urethane as Polymeric Biomaterials

Fluorescent polymeric biomaterials have got significant attention due to their promising applications in biomedical fields such as labeling, monitoring, diagnostics, imaging and tracking. Polycarbonate urethane (PCU) and 1,8-naphthalimide based fluorescent dyes separately have been studied and shown great biocompatibility and physical properties. Therefore, in this work we have taken advantage of excellent fluorescence properties of naphthalimide dye and biocompatibility of PCU, and covalently attached the fluorescent dye to the PCU (self-colored PCU). Covalent attachment can increase the stability of the dye in the biomedical applications especially when biomaterials are in contact with blood and can inhibit the release of the dye to surrounding media. DMTA, AFM, and contact angle measurement were used to study the mechanical and morphological properties of the self-colored PCU and results showed that incorporation of the dye to the PCU did not change the mechanical and morphological properties of the PCU. In addition, MTT assay, hemolysis assay, PT and aPTT assays as well as protein adsorption assay was used to evaluate the blood compatibility of PCU and self-colored PCU and results indicated great bio and blood compatibility of these materials. These great mechanical and blood compatibility properties of the self-colored PCU as well as their excellent fluorescent properties suggested that, these materials could be an ideal candidate to be use in biomedical applications in which non-invasive and non-destructive fluorescent based techniques are required.

"CinNapht" dyes: a new cinnoline/naphthalimide fused hybrid fluorophore. Synthesis, photo-physical study and use for bio-imaging.

Six-membered-diaza ring of cinnoline has been fused on naphthalimide dye to give a donor–acceptor system called CinNapht. This red shifted fluorophore, that can be synthesised in gram scale, exhibits a large Stoke shift and a fluorescence quantum yield up to 0.33. It is also characterized by a strong solvatochromic effect from green to red emission as well and can be used for bio-imaging.

White-light emission system based on cyclodextrin/surfactant supramolecular assembly

A multiple luminescence colors system was facile constructed based on the supramolecular assembly of anionic β-cyclodextrin, dodecayltrimethylaminium bromide (DTAB), a naphthalimide dye (G1) and a benzothiadiazole derivative (G2). Significantly, the fabricated system exhibited highly efficient energy transfer from G1 to G2, accompanying by fluorescence color change from blue to yellow, including white light. Furthermore, the white light emission supramolecular assembly was constructed from anionic cyclodextrin with low degree of substitution and DTAB exhibited reversible temperature responsiveness with fluorescent color changes from white to yellow.

Chiral Fluorescent Recognition by Naphthalimide.

Chirality plays a very important role in medicine, biochemistry and other fields. Because the enantiomers of chiral drugs often show different pharmacology activity, metabolism, and toxicity, therefore, the recognition of chiral molecules is very important, and has become a hot spot and frontier of modern chemical research. In this paper, a new method for recognizing chiral molecular based on naphthalimide dye(NA)⊂cucurbit[5]uril(CB[7]) assembly is developed. NA as guest can be combined with the host CB[7] to form a 1:1 NA⊂CB[7] assembly. Furthermore, this assembly was used as a fluorescent probe to recognize D/L-phenylalanine and D/L-phenylalaninol by fluorescence titration. When D-phenylalanine or D-phenylalaninol was added to NA⊂CB[7] assembly, the fluorescent intensity of assembly was partially quenched, but when L-phenylalanine or L-phenylalaninol was added to NA⊂CB[7], the fluorescence intensity of the assembly almost unchanged. Herein, chiral recognition platform based on achiral NA⊂achiral CB[7] was constructed.

Naphthalimide Dyes with Orthogonal Functional Groups for "Click" Chemistry: Attachment to Solid Supports and Applications in Drug Allergy Diagnosis.

The preparation and characterization of new functional materials for sensing have an important role in clinical diagnosis. Monitoring the surface functionalization of functional material is crucial because the final sensing properties are affected by how the (bio)molecules are immobilized on the surface of solid supports. Here, a new approach for the preparation of functional materials for biomedical diagnosis was developed. This method employs a fluorescent dye comprising 4-amino-1,8-naphthalimide with two orthogonal functional groups suitable for click chemistry. The orthogonal reactivity of these groups allows the sequential functionalization of the fluorophore, firstly with (bio)molecules, and then binding of the (bio)molecule-naphthalimide macrostructure onto the surface of a solid support. The fluorescent properties confirm the immobilization of the (bio)molecule on the surface of the solid support, without requiring other indirect methods to verify the immobilization. These functional materials were tested successfully with sera of patients, thus proving their potential application for allergic drug diagnosis.

1,8-Naphthalimide-based dual-response fluorescent probe for highly discriminating detection of cys and H2S

Hydrogen sulfide (H2S) and cysteine (Cys) are ubiquitous biological thiols in physiological and pathological processes of living systems. Their aberrant concentration levels are associated with many diseases. Hence, we developed a water-soluble fluorescent (FL) probe for H2S and Cys response. The probe was synthesized by two steps of reaction coupling between a triethylene glycol naphthalimide dye and 7-chlorobenzofurazan-4-sulfonyl chloride (CBD) dye linked by a rigid piperazine group. The probe displayed dual fluorescence emission for Cys (λem = 571 nm) and H2S (λem = 535 nm) detection, accompanied by different absorbance changes for Cys (λex = 405 nm) and H2S (λex = 486 nm). The probe could distinguish Cys and H2S from other biological thiols (GSH, Hcy) with longer wavelength or stronger fluorescence emission. Moreover, the probe was allowed to sense the exogenous or endogenous H2S and Cys with dual-emission signal (blue and red channel) in living MCF-7 cells.

Conformational Selection in Anion Recognition: cGMP-Selective Binding by a Naphthalimide-Functionalized Amido-Amine Macrocycle.

Amido-amine macrocycles with two and four naphthalimide dyes were designed to bind nucleoside monophosphates and oligonucleotides in an aqueous buffered solution. Anion-templated synthesis was used to direct the macrocyclization reaction to the [2+2] product, while high dilution conditions favored the formation of the [4+4] macrocycle with an unprecedented geometry, as revealed from the X-ray analysis. The [2+2] product was found to exhibit a remarkable binding strength and fluorescence response for cyclic guanosine monophosphate (cGMP) in an aqueous solution. To our knowledge, this is the first synthetic receptor for cGMP, which also demonstrates a high preference to bind guanine-rich sequences accomplished by a strong fluorescence quenching. The receptor conformation is very sensitive to the guest structure in an aqueous solution, thus modeling the adaptive behavior of proteins. The study of synthetic systems with a detectable conformational equilibrium represents a great potential for understanding highly specific and tightly regulated interactions in biological systems.

Naphthalimide-based optical turn-on sensor for monosaccharide recognition using boronic acid receptor.

A highly selective and sensitive fluorescent sensor for the determination of fructose is developed. The fluorescent sensor was prepared by incorporating a new naphthalimide dye with a planar structure as a selectophore and graphene oxide (GO) nanoplatelets as a quencher for rapid optical detection of fructose. The designed probe, made with the high fusion loop-containing dye, along with the GO nanoplatelets, detected fructose over the other monosaccharides very well. The proposed sensor displays a linear response range of 7 × 10−5 to 3 × 10−2 M with a low limit of detection of 23 × 10−6 M in solution at pH 7.4. This sensor shows a good selectivity towards fructose with respect to other saccharides. The proposed sensor was then applied to the determination of fructose in human plasma with satisfactory results.