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TETRAHEDRON · 2015 · IF 2.641

A novel colorimetric and fluorescent probe for detecting fluoride anions: from water and toothpaste samples

Mingming Yu,Jie Xu,Chao Peng,Zhanxian Li,Chunxia Liu,Liuhe Wei

Based on 8-hydroxyquinoline, a 1,8-naphthalimide-derived colorimetric and fluorescent probe was synthesized for naked-eye and fluorescent recognition of F − (from both tetrabutylammonium fluoride and NaF) with high sensitivity and excellent selectivity. The probe can be employed to detect F − quantitatively within certain concentration range, and the detection limit could be as low as 1.8 μM for tetrabutylammonium fluoride and 9 μM for NaF. With this probe, the tests for fluorine contents in tap water, water sample from Eyebrow Lake and several brands of toothpastes were successfully performed.

CAS / MDL: 7446-08-4
研究领域: 分析化学 · 环境科学
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Journal of Analysis and Testing · 2021 ·Vol. 6 ·期 3 ·296-307 · IF 0

Electrochemiluminescence of 1,8-Naphthalimide-Modified Carbon Nitride for Cu2+ Detection

Liu Feng-Yu,Zhang Tong-Kai,Zhao Yi-Long,Ning Hong-Xia,Li Fu-Sheng

It is essential to screen novel luminophores and co-reactants for the development of electrochemiluminescence (ECL) systems. In this work, a series of 1,8-naphthalimide-modified graphitic carbon nitride (CN/1,8-NDI x ) ECL luminophores were successfully developed for the quantitative determination of Cu 2+ with K 2 S 2 O 8 as a co-reactant. When CN/1,8-NDI x was immobilized on the surface of the glassy carbon electrode (GCE), a strong ECL signal could be produced (at a potential of − 1.3 V vs. Ag/AgCl), which was threefold stronger than that of unmodified g-C 3 N 4 . The intensity of ECL could be linearly quenched by Cu 2+ over a concentration range from 5 × 10 −9 to 1 × 10 −4  mol/L, and with a low limit of detection (LOD) of 0.86 nmol/L. Our results may provide a new perspective on the novel ECL platforms development.

研究领域: 分析化学 · 环境科学
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LIQUID CRYSTALS · 2024 · IF 2.4

Chiral fluorescent liquid crystal polymers containing 4-bromo-1,8-naphthalimide – synthesis and properties

Rui-Zhe Zhou,Yan Zhang,Ji-Feng Gao,Shuai-Yin Ma,Hong-Shuang Zhang,Xiao-Zhi He

By introducing two cholesteric liquid crystal monomers with different chain lengths (M1 and M2) and brominated naphthalimide fluorescent monomer (M3) into polymethyl hydrosiloxane, a series of fluorescent cholesteric liquid crystal polymers (FL-LCP) was prepared, which not only have excellent performance of liquid crystal and fluorescence but also own performance of selective reflection. Their chemical structures were confirmed to be in accord with molecular design by FT-IR and 1 H NMR spectroscopy, and found them with excellent thermal stability, mesomorphic behaviour and thermal performance by TGA, POM, DSC and XRD, and confirmed all the polymers belonged to the cholesteric phase. The FL-CLCPs emitted different intensity fluorescence under UV light, and conclusions about the relationship between fluorescence and temperature had been drawn. A comparative study was conducted on the fluorescence properties of powders and films of monomers and polymers.

研究领域: 材料科学 · 化学
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DYES AND PIGMENTS · 2021 · IF 4.889

Investigation on the construction, photophysical properties and dyeing mechanism of 1,8-naphthalimide-based fluorescent dyes suitable for dyeing wool fibers in supercritical CO2

Mengke Jia,Haina Hu,Xiaoqing Xiong,Lihua Lyu,Hongjuan Zhao,Shubiao Zhang,Jun Hou

Technology of supercritical carbon dioxide (scCO 2 ) dyeing has been used in dyeing synthetic and natural fibers . It is important to understand the scCO 2 dyeing mechanism owing to the possibility of using this knowledge to design dyes that are suitable for scCO 2 dyeing. Here, using the N-site and 4-site modification of 1,8-naphthalimide matrix, six fluorescent dyes ( 1 , 2 , 3 , 4 , 5 , and 6 ) with fluorescent properties were synthesized; dyeing performance and fluorescent images indicate that all the synthesized dyes can be utilized for scCO 2 dyeing wool fibers . Therefore, the dyed wool fibers possess not only conventional dyeing characteristics but also luminescent properties. Especially, the dyed wool fibers with solid free fluorescent dye 2 exhibit strong yellow-green fluorescence. Owing to the lack of proper fixation process, the fixation rate of these six fluorescent dyes on wool fibers was not relatively high. Thus, the dye 7 with an active group N-hydroxysuccinimide (NHS) was synthesized to improve the binding force between dyes and wool fibers and it can react with the –NH 2 group in wools, which results in that the fixation rate of the synthesized dye 7 reaches approximately 91% through chemical combination. Mass spectra prove that the byproduct of 7 reacting with the amino group of wool fibers is not corrosive to dyeing equipment, which realizes the eco-friendly fluorescent dyeing of wool fibers in scCO 2 . Our results proved that the fluorescent dyes with conjugated system can overcome the problem of fluorescence quenching in natural fibers. Meanwhile, our strategy of constructing fluorescent dyes and the proposed dyeing mechanism will be helpful to develop reactive disperse dyes that are suitable for scCO 2 dyeing.

研究领域: 化学 · 材料科学 · 纺织工程
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SENSORS AND ACTUATORS B-CHEMICAL · 2017 · IF 5.401

Isocyano-functionalized, 1,8-naphthalimide-based chromophore as efficient ratiometric fluorescence probe for Hg2+ in aqueous medium

Xicun Zhang,Wei Shi,Xin Chen,Zhengfeng Xie

A type of isocyano-functionalized, 1,8-naphthalimide-based chromophore ( M2 ) was successfully synthesized from its primary amine-derivatived precursor ( M1 ) compound. The chemical structure of M2 was verified by FT-IR, NMR and HRMS analyses. The presence of electron-withdrawing isocyano group brought significant influence to the optical properties of M2 . Distinct from the yellowish green emission of its precursor ( M1 ), M2 emitted ultraviolet light (with the emission peak at ∼389   nm, excited by 352   nm) in THF-water [V THF /V water   =   3/7, buffered with 5   mM sodium dihydrogen phosphate-disodium hydrogen phosphate (PB), pH   =   7.4] co-solvent system. Interestingly, M2 exhibited distinctive and selective optical response (with significant enhancement of emission at ∼560   nm) toward Hg 2+ . In Hg 2+ titration process, PL spectra of M2 displayed contiguous ratiometric alteration (simultaneous decreasing at 389   nm and increasing at 560   nm). Hg 2+ -assisted hydration of isocyano group to amino group on M2 was proposed as the plausible probing mechanism in this current case.

研究领域: 分析化学 · 环境科学 · 材料科学
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2012 · IF 3.07

A reusable naphthalimide-functionalized magnetic fluorescent nanosensor for the simultaneous determination and removal of trace Hg2+ in aqueous solution

Jie Zhao,Baocun Zhu,Haiqin Yu,Liangguo Yan,Qin Wei,Bin Du

On the basis of high selective and sensitive interaction of 1,8-naphthalimide with Hg 2+ and the formation of stable neutral imide-Hg-imide complexes, we designed and synthesized a novel magnetic fluorescent sensor ( S1 ) employed Fe 3 O 4 magnetic nanoparticles and 1,8-naphthalimide fluorescent sensor. Under optimum conditions, S1 exhibits the high selectivity toward Hg 2+ over other metal ions, with the detection limit of 1.03   ×   10 −8   M. We demonstrated that a reliable fluorescence response of S1 toward Hg 2+ over a broad pH range (pH   =   5.0–9.0) could be reused at least four cycles. The maximum sorption capacity of S1 was about 5.6   mg   g −1 . In addition, the removal of Hg 2+ in water was achieved by the aggregation-induced sedimentation (AIS) strategy. Moreover, the suspended magnetic nanoparticles could be removed by external magnetic field , and the secondary pollution was avoided. The above-mentioned results indicate that this approach may serve as a foundation of the preparation of the multifunctional magnetic fluorescent sensor for simple, rapid, and simultaneous determination and removal of trace Hg 2+ and other pollutants in environmental samples.

研究领域: 分析化学 · 环境科学
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JOURNAL OF INORGANIC BIOCHEMISTRY · 2024 · IF 3.8

A series of DNA targeted Cu (II) complexes containing 1,8-naphthalimide ligands: Synthesis, characterization and in vitro anticancer activity

Kehua Wang,Ling Wang,Zhuye Shang,Xingzhi Yang,Hongmei Li,Xiaochun Wang,Mingchang Zhu,Qingtao Meng

Copper(II) complexes are very promising candidates for platinum-based anticancer agents. Herein, three Cu (II) complexes ( 1 – 3 ) containing 1,8-naphthalimide ligands were synthesized and characterized by FT-IR, elemental analysis, ESI-MS and single crystal X-ray diffraction (complex 3 ). In addition, a control compound (complex 4 ) without 1,8-naphthalimide ligand was synthesized and characterized. The in vitro anticancer activity of the synthesized complexes against five cancer cell lines and one normal cell line was evaluated by MTS assay. The results displayed the antitumor activity of complexes 1 – 3 was controlled by the aliphatic chain length of ligands, their cytotoxicity was in the order 3  >  2  >  1 , giving the IC 50 values ranging from 2.874 ± 0.155 μM to 31.47 ± 0.29 μM against five cancer cell lines. Complex 4 showed less activity in comparison with complex 1 – 3 . Notably, complexes 1 – 3 displayed much higher selectivity (SI = 2.65 to 10.16) compared to complex 4 (SI = 1.0), indicated that the introduction of 1,8-naphthalimide group not only increased the activity of this series of compounds but also enhanced their specific selectivity to cancer cells. Compound 3 induced apoptosis in cancer cells and blocked the S-phase and G2/M of cancer cells. The interaction with DNA of complexes 3 and 4 was studied by UV/Vis spectroscopic titrations, competitive DNA-binding experiment, viscometry and CD spectra. The results showed that complex 3 interacted with DNA in an intercalating mode, but the interaction mode of compound 4 with DNA was electrostatic interaction.

研究领域: 药物化学 · 分子生物学 · 肿瘤学
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DYES AND PIGMENTS · 2022 · IF 5.122

Several Golgi targeting fluorescence markers based on 1,8-naphthalimide derivatives with amide and long carbon chain

Xu-Chen Feng,Gang Zhang,Ru Sun,Yu-Jie Xu,Jian-Feng Ge

As an important organelle, the main function of the Golgi apparatus is to further modify and deliver proteins synthesized by the endoplasmic reticulum (ER). Dyshomeostasis of the Golgi appartus can cause many serious diseases. Therefore, monitoring the normal functioning of the Golgi appartus is particularly important. However, only a few commercially Golgi markers are available till now. In this work, three 1,8-naphthalimide related Golgi markers ( 4a - c ) with the combination of amide and long carbon chain were designed and synthesized, their maximum emission wavelengths could reach 500–575 nm with high fluorescence quantum yields . Moreover, they possessed low cytotoxicity (cell viabilities >82%). Cell experiments exhibited that dyes 4a - c could rapidly and accurately mark the Golgi apparatus. To discuss the origin of their targeting ability, compounds 5–7 with independent amide or long carbon chain were additionally prepared. With the separation of amide and long carbon chain in compound 5 – 7 , the targeting ability was lost. The experiments showed that the targeting ability of 4a - c resulted from the combination of amide and long carbon chain structure. Also, the results may provide a new idea for designing organelle markers.

研究领域: 细胞生物学 · 医学
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Materials Science & Engineering C-Materials for Biological Applications · 2015 · IF 3.088

Fluorescent molecularly imprinted polymers based on 1,8-naphthalimide derivatives for efficiently recognition of cholic acid

Zhifeng Xu,Peihong Deng,Siping Tang,Junhua Li

Fluorescent molecularly imprinted polymers (MIPs) have attracted increasing attentions in recent years due to their high selectivity and sensitivity for target molecules. In this study, two cholic acid imprinted fluorescent polymers, i.e., MIP 1 and MIP 2 , were prepared using 4-dimethylamino-N-allylnaphthalimide (F 1 ) and 4-piperazinyl-N-allylnaphthalimide (F 2 ) as the fluorescent functional monomers, respectively. The fluorescence intensity of MIP 1 decreased linearly with the increase of the template concentration in the range of 1.50–120.0   μM, while the fluorescence intensity of MIP 2 increased linearly with the increase of the template concentration in the range of 0.40–110.0   μM. The detection limits of MIP 1 and MIP 2 for cholic acid were 0.42 and 0.083   μM, respectively. The mechanisms of the fluorescence responsive of the imprinted polymers were discussed. The results of fluorescence measurement and binding experiments demonstrated that both imprinted polymers have high recognition abilities and binding affinities for the template. The imprinted polymers have been successfully applied to the determination of cholic acid in human serums. The present study indicated that 1,8-naphthalimide can be used as a modular building block for design and construction of various fluorogenic molecularly imprinted materials for practical sensing and separation.

研究领域: 分析化学 · 生物传感 · 材料科学
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JOURNAL OF APPLIED POLYMER SCIENCE · 2024 ·Vol. 142 ·期 2 ·e56358 · IF 2.7

Facile fabrication of luminescent ultra-high molecular weight polyethylene fibers based on novel alkyl-substituted 1,8-naphthalimide fluorescent dyes

Leixin Wu,Jing Ye,Jiahui Wu,Wo Nie,Xiyu Song,Liu Hu

Ultra-high molecular weight polyethylene (UHMWPE) fiber, with excellent light resistance, and chemical resistance, is one of the most important high-performance fibers. However, the high hydrophobicity and crystallinity make it difficult to color, restricting the development of colored fluorescent UHMWPE protection materials. In this study, three hydrophobic fluorescent dyes ( NC4 , NC8 , NC16 ) for fluorescent dyeing of UHMWPE were developed by introducing alkyl substituents of different lengths (butyl, octyl, and hexadecyl) and polar cyano groups onto 4-NH-1,8-naphthalimide fluorescent chromophore. The relationship between the structures and the application performance was studied, and theoretical calculations were combined to explore the influence of the substituents on the spatial and electronic effects of fluorescent dyes. With the extension of the alkyl chain, the dye-uptake rate and building-up property was enhanced, and the equilibrium dye-uptake rates for NC4 , NC8 , and NC16 were 18.21%, 93.22%, and 62.96%, respectively. NC8 , which was proven to have high hydrophobicity and maximum dipole moment, exhibited the highest dye-uptake rate. The dyed UHMWPE fabrics exhibited strong yellow-green fluorescence. This study provides a facile strategy for constructing luminescent UHMWPE protection materials.

CAS / MDL: 584-08-7 31643-49-9
研究领域: 材料科学 · 高分子化学
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DYES AND PIGMENTS · 2020 · IF 4.613

Convenient construction of fluorescent markers for lipid droplets with 1,8-naphthalimide unit

Jing-Yang Ni,Xiao-Feng Weng,Ru Sun,Yu-Jie Xu,Jian-Feng Ge

1,8-Naphthalimide is widely applied in the construction of probes because it is easy to be modified. However, 1,8-naphthalimide has been reported rarely in the application of organelle labelling especially lipid droplets (LDs). Herein, three types of amine compounds, aliphatic amine ( a , b ), aromatic amine ( c , d ) and heterocyclic amine ( e , f ), were chosen to construct fluorescent dyes ( 1a - 1f ) with 4-bromo- N -butylnaphthalimide ( 1 ) by Ullmann reaction. The maximum emission wavelength ranged from 490 nm to 550 nm. What's more, 1a-1e showed high fluorescence quantum yields (0.54–0.93) in chloroform and 1e-1f had excellent photostability (>92%). In addition, the cell imaging experiment showed that they could label lipid droplets for HeLa cancer cells and L929 normal cells with extremely low toxicity. This work realizes the classical fluorophore 1,8-naphthalimide to synthesize a series of LDs markers without complex synthesis steps.

研究领域: 化学 · 生物学 · 材料科学
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2011 · IF 2.13

A 1,8-naphthalimide group modified magnetic silica nanoparticles INHIBIT logic gate with H+ and F− as inputs

Xin Tian,Zhengping Dong,Yifan Huang,Jiantai Ma

In this work, molecular logic element modified multifunctional silica nanoparticles having high magnetization have been successfully prepared. These multifunctional nanoparticles were characterized by Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), Elementary analysis, X-ray powder diffraction (XRD) and Vibrating sample magnetometer (VSM). The characterization datum indicated that the organic ligand was successfully grafted on the surface of the magnetic silica nanoparticles . The fluorescent changes of the hybrid material upon the addition of cations (H + , F − and their mixture) is utilized as an INHIBIT logic gate at the molecular level, using the fluorescence intensity signal as output.

研究领域: 纳米医学 · 生物传感器 · 分子诊断 · 化学生物学 · 智能材料
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