92874-17-4Relevant academic research and scientific papers
Novel 1,8-naphthalimide dye for multichannel sensing of H+ and Cu2+
Chen, Yufen,Tang, Tengxuan,Chen, Yuhua,Xu, Dongmei
, p. 2379 - 2393 (2018)
A novel 1,8-naphthalimide dye with simple structure has been produced by a facile synthetic method for colorimetric and fluorescent sensing of H+ and Cu2+. In CH3CN/H2O (1/1, v/v), the dye could monitor H+ using dual channels (ratiometric absorbance and fluorescence intensity change) from pH 6.2 to 12.0. Meanwhile, in the pH range of 1.9–5.2, the dye could also be used to detect Cu2+ using triple channels [ultraviolet–visible (UV–Vis) absorption, fluorescence intensity reduction, as well as fluorescence blueshift]. The detection limits for Cu2+ evaluated by colorimetric and fluorescent titration were 6.10?×?10?7 and 2.62?×?10?7?M, respectively. The dye exhibited specific selectivity and sensitivity for H+ and Cu2+ over various coexisting metal ions. Moreover, the sensing mechanism of the dye for H+ and Cu2+ was carefully examined.
Development of naphthalimide-functionalized thermochromic conjugated polydiacetylenes and their reversible green-to-red chromatic transition in the solid state
Mergu, Naveen,Kim, Hyorim,Heo, Gisu,Son, Young-A.
, p. 355 - 362 (2019)
Development of PDAs has received great attention in many fields due to their optical and chromatic properties towards external stimuli. In this article, two novel PDAs (NPI-PDA1 and NPI-PDA2) containing naphthalimide as a head group are designed and synthesized through self-assembly followed by topochemical polymerization, and these compounds show a reversible green-to-red colorimetric transition upon heating. PEO-embedded films are fabricated to facilitate the investigation of the thermochromic properties, and the surface morphologies of the films are observed by SEM analysis. The thermochromic behavior and color transitions are observed using photography and electronic absorption spectroscopy. The changes in the extended ene-yne conjugated system of the polymer during heat treatment are successfully monitored by Raman spectrometry. Moreover, PDA-embedded crayon wax-based hand-writable pens are fabricated and used efficiently on a solid substrate. NPI-PDA1 and NPI-PDA2 display excellent reversibility in the temperature ranges of 25–120 °C and 25–160 °C, respectively in the PEO polymer and paraffin wax matrices.
Combination of sensor potential and antimicrobial activity of a new 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide
Staneva, Desislava,Vasileva-Tonkova, Evgenia,Makki, Mohamad S.I.,Asiri, Abdullah M.,Grabchev, Ivo
, p. 88 - 94 (2014)
A blue emitting 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide bearing a dimethylaminoethyloxy group as a receptor fragment for metal ions and protons has been designed and synthesized. The basic photophysical properties of the compound have been investigated in organic solvents of different polarity. The detection of different metal cations (Pb2+, Cu2+, Cd2+, Co2+, Zn2+and Mn2+) has been studied by fluorescence spectroscopy. Depending on pH, the new compound shows "off-on" switching from alkaline to acid media. A new complex of Cu(II) with the 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide has been synthesized and characterized. The antibiotic activity of the complex was evaluated against some bacterial and yeast cultures.
Fluoride ion activated CO2 sensing using sol-gel system
Liu, Yifan,Lee, Dayoung,Zhang, Xin,Yoon, Juyoung
, p. 658 - 663 (2017)
CO2 detection has drawn a lot of attention due to its important role in the environment and in medical diagnosis. Two amino substituted naphthalimides are reported as new anion-induced CO2 selective chemosensors. The new naphthalimides contain either a hydrazinecarbothiourea or a hydrazinecarboxylate group which served as an anion recognition site. The addition of F? induced a distinct color change and a fluorescent quenching effect, which was revived by subsequent addition of CO2. The naphthalimide bearing a hydrazinecarboxylate group also served as an organo gelator, which showed a unique sol-gel transition as well as color/fluorescent changes with F? and CO2.
A novel ratiometric fluorescent probe for quantitative detection of isocyanates in air
Chen, Kai,Chen, Wanjuan,Sun, Jin,Bai, Mingyang,Gao, Zhenzhong,Hou, Xianfeng
, (2020)
Isocyanates are important industrial raw materials, but they are hazardous to human health. Especially, gaseous isocyanates cause serious public health problems. Therefore, it is significant to monitor isocyanates in air. In this work, a novel ratiometric fluorescent probe based on a new fluorophore platform, which is designed by inserting a styryl π-bridge between donor and acceptor units of 1, 8-naphthalimide, was developed for quantitative detection of gaseous isocyanates. In the presence of isocyanates, fluorescence of probe solution changed from orange to yellow-green, which caused by alteration of substituent at the 4th position of styryl group resulted from reaction between isocyanates and probe, thus achieving ratiometric detection for isocyanates. And this probe exhibited a fast, sensitive and selective response towards isocyanates. Furthermore, probe solution absorption method was employed to detect quantitatively isocyanates in air. This strategy may be a powerful tool for monitoring isocyanates in air, and also provide a referable approach for detection of volatile organic compounds in air.
Fabrication of double emission enhancement fluorescent nanoparticles with combined pet and aiee effects
Chang, Cheng-Chung,Wu, Hsing-Ju
, (2020)
The major challenge in the fabrication of fluorescent silica nanoparticles (FSNs) based on dye-doped silica nanoparticles (DDSNs) is aggregation-caused fluorescence quenching. Here, we constructed an FSN based on a double emission enhancement (DEE) platform. A thio-reactive fluorescence turn-on molecule, N-butyl-4-(4-maleimidostyryl)-1,8-naphthalimide (CS), was bound to a silane coupling agent, (3-mercaptopropyl)-trimethoxysilane (MPTMS), and the product N-butyl-4-(3-(trimethoxysilyl-propylthio)styryl)-1,8-naphthalimide (CSP) was further used to fabricate a core–shell nanoparticle through the St?ber method. We concluded that the turn-on emission by CSP originated from the photoinduced electron transfer (PET) between the maleimide moiety and the CSP core scaffold, and the second emission enhancement was attributed to the aggregation-induced emission enhancement (AIEE) in CSP when encapsulated inside a core–shell nanoparticle. Thus, FSNs could be obtained through DEE based on a combination of PET and AIEE effects. Systematic investigations verified that the resulting FSNs showed the traditional solvent-independent and photostable optical properties. The results implied that the novel FSNs are suitable as biomarkers in living cells and function as fluorescent visualizing agents for intracellular imaging and drug carriers.
Green synthesis of fluorescent N,O-chelating hydrazone Schiff base for multi-analyte sensing in Cu2+, F? and CN? ions
Saini, Neeraj,Prigyai, Nicha,Wannasiri, Chidchanok,Ervithayasuporn, Vuthichai,Kiatkamjornwong, Suda
, p. 215 - 225 (2018)
A colorimetric and fluorometric hydrazone Schiff's base derived from dehydroacetic acid by three-steps and high-yield syntheses under green approach employing ethanol as a solvent has been prepared. Multi-analyte sensing for both metal cation (Cu2+) and anions (F? and CN?), with high sensitivity and competitive selectivity, was encountered. The sensing mechanism of anion detection found to be deprotonation of N–H and O–H moieties in the presence of ions. However, metal cation like copper(II) ions chelation with sensor, leads to diminish intra-molecular charge transfer (ICT) with chelation induced quenching of fluorescence (CHQF). Contrary, anionic interaction ensued in heightened ICT as well as photo-induced electron transfer (PET) processes. The Job's plots interpretation rendered stoichiometry of 2:1 with Cu2+/F? and 1:1 with CN?. Moreover, the detection limits of 0.962 ppm (Cu2+), 0.023 ppm (F?) and 0.073 ppm (CN?) were much lower than WHO guidelines. Further, either water or methanol was employed to differentiate F?/CN? ions with sensor in THF, with prominent visible naked eye and fluorometric responses.
Cis/trans Fluorescent Recognition by Naphthalimide Dyes???CB [7] Assembly
Li, Junyong,Gu, Xiaomin,Yuan, Xiaosheng,Qiu, Qiqi,Sun, Jie,Wang, Haibo
, p. 1219 - 1224 (2016)
A novel method to recognize cis/trans isomers was studied here. The naphthalimide dye as guest could bind with host cucurbit [7]uril (CB [7]) and 1:1 naphthalimide dye???CB [7] assembly was formed. Moreover, this assembly was used as a fluorescent probe to recognized Fumaric acid (FA) and maleic acid (MA) via fluorescence titration. Two carboxyls in MA are in the same side, they could form stable interaction with the assembly and the fluorescence intensity decreased obviously when naphthalimide dye???CB [7] was titrated by MA (nearly quenched in 1.5 equiv). But two carboxyls in FA are in opposite sides, the interaction between FA and the assembly was weak and not stable, and the fluorescence intensity changed inconspicuously when the assembly was titrated by FA.
A two-channel chemosensor for the optical detection of carboxylic acids, including cholic acid
Esteban-Gomez, David,Fabbrizzi, Luigi,Licchelli, Maurizio,Sacchi, Donatella
, p. 2670 - 2675 (2005)
A neutral receptor, in which a urea fragment has been equipped with two naphthaleneimide subunits, on interaction with acetate, in a DMSO solution, undergoes deprotonation of one of the N-H fragments; an event which is signalled by a yellow-to-red colour change and by the quenching of the blue fluorescence of the naphthalneimide subunit, with no competition by a number of anions (phosphate, nitrate, sulfate, chloride or bromide). This procedure can be employed for the visual and spectroscopic detection of cholic acid, even in presence of the other competing bile acids, such as glycocholic and taurocholic. The Royal Society of Chemistry 2005.
Ratiometric chemodosimeter: An organic-nanofiber platform for sensing lethal phosgene gas
Maiti, Kalipada,Ghosh, Debasish,Maiti, Rituparna,Vyas, Veena,Datta, Pallab,Mandal, Debabrata,Maiti, Dilip K.
, p. 1756 - 1767 (2019)
Herein, we report the fabrication of organic nanofibrils, using electrospun 3-oxime-4-hydroxy-1,8-naphthalic-n-butylimide (R1)-doped polycaprolactone (PCL), for application as a gaseous phosgene-specific sensing device. The phosgene-mediated adsorption of the nanofibers gives rise to an observable colorimetric switch from brown-red to pale greenish-yellow and a synchronized ratiometric spectral emission with significantly high Stokes shift. The high surface to volume ratio and innovative properties of the nanofiber mats lead to the diminution of response time in comparison to the composite film of the same materials. Proficient gas penetration allows a fast chemical reaction, which is proportional to the phosgene concentration and delivers a very low detection limit of 0.087 ppm. To the best of our knowledge, this is the lowest limit of detection of gaseous phosgene for any robust protocol to date. Confocal fluorescence imaging and scanning electron microscopy (SEM) studies revealed partial deformation on the surface of the nanomaterials upon the adsorption of phosgene, indicating the phosgene-mediated chemical transformation. The fluorescent naphthalic-oxime with an elevated specific surface area of nanofibrous polymeric supports proffers fast optical and visual phosgene detection for industrial and environment application. Importantly, the LOD of gaseous phosgene in all solid protocols used is far lower than the safe phosgene concentration levels for human exposure.
