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ChemistrySelect · 2024 ·Vol. 9 ·期 28 ·e202402061 · IF 1.9

Direct C−H Alkylation of Naphthoquinone with Acetone and 1,3-Dicarbonyl Compounds via Radical Cross Dehydrogenation Coupling

Jiankang Ou,Haoyu Liu,Zeguo Fang,Qian Zhang,Dong Li

Graphical Construction of C−C bonds of alkyl-substituted naphthoquinones through C−H/C−H cross dehydrogenation coupling of naphthoquinones with acetone and 1,3-dicarbonyl compounds was developed. A direct C−H alkylation of naphthoquinones with acetone and 1,3-dicarbonyl compounds was developed to construct C−C bonds of alkyl-substituted naphthoquinone derivatives. It proceeded through an oxidative radical cross dehydrogenation coupling process under simple and mild conditions. This method provides a facile and efficient route for synthesis of functionalized naphthoquinones from readily available feedstocks.

研究领域: 有机化学 · 合成化学
✓ 已验证 DOI 高影响因子
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JOURNAL OF MATERIALS SCIENCE · 2019 ·Vol. 55 ·期 2 ·806-816 · IF 3.442

High-performance naphthalenediamine-based polybenzoxazine and its cured epoxy resin

Ren Shitong,Zhang Shaoyue,Zhao Weibo,Wang Wei

To obtain thermosets with high performance, a 1,5-naphthalenediamine (NDA)-based benzoxazine (NB) is successfully synthesized and used as a novel hardener for diglycidyl ether of bisphenol-A (DGEBA). The structure of NB is confirmed by FT-IR and NMR. The curing behaviors of NB and NB/DGEBA are studied by non-isothermal DSC, and the properties of the resulting thermosets are measured by DMA and TGA. The results show that NB’s thermoset has excellent thermal–mechanical property, thermal stability, and flame retardancy, with storage modulus at 30 °C ( \( E^{{\prime }} \) ) of 2.4 GPa, 10% weight loss temperature ( T 10% ) of 366 °C, glass transition temperature ( T g ) of 279 °C, and char yield at 800 °C in nitrogen (CY) of 60.6%. NB-cured DGEBA possesses better stiffness, thermal stability, flame retardancy, and high-temperature resistance than NDA-cured DGEBA, as indicated by the 1.2 GPa higher \( E^{{\prime }} \) , 11 °C higher T 10% , 21% higher CY, and 50 °C higher T g .

研究领域: 材料科学 · 化学工程
✓ 已验证 DOI 高影响因子
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Materials · 2022 ·Vol. 15 ·期 22 ·8014 · IF 3.748

Synthesis and Characterization of Polyimides with Naphthalene Ring Structure Introduced in the Main Chain

Jiang-Rong Luo,Yi-Dong Liu,Heng Liu,Wei-Peng Chen,Ting-Ting Cui,Liangang Xiao,Yonggang Min

In this paper, a new aromatic diamine monomer 4,4′-(2,6-naphthalenediyl)bis[benzenamine]) (NADA) was synthesized and a series of modified PI films containing naphthalene ring structure obtained by controlling the molar ratio of NADA monomer, ternary polymerization with 4,4′-oxydianiline (ODA), and pyromellitic dianhydride (PMDA). The effects of the introduction of the naphthalene ring on the free volume and various properties of PI were investigated by molecular dynamic simulations. The results show that the comprehensive properties of the modified films are all improved to some extent, with 5% thermal weight loss temperature (Td5%) of 569 °C, glass transition temperature (Tg) of 381 °C, tensile strength of 96.41 MPa, and modulus of elasticity of 2.45 GPa. Dielectric property test results show that the dielectric constant (Dk) of the film at 1 MHz is reduced from 3.21 to 2.82 and dielectric loss (Df) reduced from 0.0091 to 0.0065. It is noteworthy that the PI-1 dielectric constant is reduced from 3.26 to 3.01 at 10 GHz with only 5% NADA doping, which is expected to yield the best ratio and provide the possibility of industrial production.Keywords:naphthalene-containing cyclic diamine;terpolymer;polyimide film;dielectric properties

研究领域: 材料科学 · 高分子化学 · 电气工程
✓ 已验证 DOI PubMed 高影响因子
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CHEMICAL ENGINEERING JOURNAL · 2021 · IF 13.273

Enhancement of photocatalytic activity of TiO2 by immobilization on activated carbon for degradation of aquatic naphthalene under sunlight irradiation

Ganning Zeng,Hanzhang You,Mingming Du,Yan Zhang,Yimei Ding,Chengda Xu,Bo Liu,Bing Chen,Xiangliang Pan

Remediating and controlling PAHs (Polyaromatic Hydrocarbons) contamination in the environment is essential all over the world. Nano-TiO 2 immobilized on large surface area adsorbent is a kind of emerging endeavor to enhance the photo-catalysis performance. In this paper, activated carbon samples (ACs) were synthesized by using a kind of subtropical macroalgae, i.e., Sargassum Horneri ( S.H. ) as raw material. ACs activated by FeCl 3 , ZnCl 2 , a composite activators mixture of FeCl 3 and ZnCl 2 (CA) were selected to immobilize nano-TiO 2 in aquatic environment, and naphthalene degradation performance of these materials was systematically assessed. The results showed that ACs could provide more activated space for naphthalene photocatalytic reaction, in which Zn 2+ helped to hold relative high specific surface area, Fe 3+ helped to extend the valid light responsive wavelength, and CA could take advantage of both metal ions, with the largest whole volume and surface functional groups. The highest naphthalene degradation efficiency of TiO 2 /AC-CA under simulated sunlight could arrive to 77.5%, while those of TiO 2 /AC-FeCl 3 and TiO 2 /AC-ZnCl 2 were 65.0%, 54.5%, respectively. Meanwhile, the pH-resistance and reusing capability of TiO 2 /AC-CA are better than those of other TiO 2 /ACs. The results helped to clarify the synergistic mechanism of AC and TiO 2 in photo-catalysis, especially the metal ions’ role in combining the two materials, and showed the industrial potential of S.H. in PAHs contamination.

研究领域: 环境科学 · 材料科学
✓ 已验证 DOI 高影响因子
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Materials Today Energy · 2021 · IF 7.311

High performance n-type thermoelectric material based on naphthalenediimide radical anions

D. Zhao,Q. Jiang,Y. Jia,J. Zhou,N. Zheng,D. Hu,Y. Ma

An ideal organic thermoelectric (TE) material should possess features that would be low-cost, of high performance, easy to process, and non-toxic, but it is rare to find materials that meet these requirements. Naphthalenediimide (NDI), as a common and cheap industrial pigment, displays strong intermolecular inaction and good n-type semiconductor character. However, due to the strong interaction of π-π and hydrogen bond interaction, NDI usually exhibited poor solubility, making it difficult to process in solution. Herein, we demonstrated that the unsubstituted NDI could form a suspension mixed with NDI radical anion state by phenyl lithium doping, which consequently can be used to prepare dense film by drop-casting for TE application. More importantly, by optimizing the doping ratio, the TE film reached electrical conductivity of 0.11 S cm −1 and Seebeck coefficient of −1289 μV K −1 . Eventually, a high power factor up to 18.8 μW m −1  K −2 and ZT value of 0.053 was obtained, which is one of the best TE performance achieved in n-type NDI-based TE materials. This work suggests the simple strategy of utilizing commercially mature molecules to develop organic TE materials with high performance.

研究领域: 材料科学 · 有机电子学
✓ 已验证 DOI 高影响因子
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Inorganic Chemistry Frontiers · 2020 ·Vol. 7 ·期 22 ·4477-4487 · IF 5.958

Achievement of intrinsic white light emission by hybridization-deformable haloplumbates with rigid luminescent naphthalene motifs

Xiang-Ling Lin,Bin Chen,You-Ren Huang,Kai-Yue Song,Pan-Ke Zhou,Lu-Lu Zong,Hao-Hong Li,Zhi-Rong Chen,Rong Jiang

The design of single-component broadband photoemitters with high stability is imperative for the development of next-generation WLEDs. In this work, 1D cationic haloplumbate chains and rigid luminescent naphthalene dicarboxylate (2,6-ndc) with a larger conjugated system were used to construct crystalline single-component broadband photoemitters, i.e. formulated as [(Pb4X2)(ndc)4·A2]n (X = Cl, Br, and I, A = (CH3)3NH+ and (CH3)2NH2+). These hybrids are 3D networks built from flexible 1D cationic (Pb4X2)6+ chains and rigid 2,6-naphthalene dicarboxylic acid ligands. The variation of halogen atoms from Cl to Br/I with higher polarity can switch the holo-directed geometry to the hemi-directed geometry with different distorted degrees. The larger conjugated system of 2,6-ndc leads to strong individual blue adsorptions and emissions. In particular, the Br- and I-analogues with hemi-directed geometries can give rise to additional red emissions, corresponding to the presence of stereochemical activities of Pb centers. Consequently, Br- and I-analogues are white-light emitters containing red emissions stemming from deformable haloplumbate and blue emissions originating from luminescent naphthalene motifs. Interestingly, haloplumbate-based emissions are thermally tunable, and those of naphthalene are generally inactive to thermal stimulus. As a result, tunable emissions from blue/white to yellow can be achieved. The higher quantum yield of Br-analogues can be assigned to their worse haloplumbate connectivity, which can enhance the electron–phonon coupling. In all, the combination of flexible haloplumbate chains with larger π-conjugated fluorophores is an efficient strategy for the construction of tunable broadband photoemitters.

研究领域: 材料科学 · 光学
✓ 已验证 DOI 高影响因子
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APPLIED CLAY SCIENCE · 2020 · IF 4.605

Persistent organic pollutants removal via hierarchical flower-like layered double hydroxide: Adsorption behaviors and mechanism investigation

Zebing Zhu,Sida Ouyang,Peng Li,Lili Shan,Ruonan Ma,Ping Zhang

Nanostructured hierarchical flower-like MgAl layered double hydroxide (HMA-LDH) was synthesized via the one-pot soft-template method and employed for the adsorption of persistent organic pollutants: anionic methyl orange (MO) and non-ionic naphthalene (NAP). The adsorption performance and mechanism comparison of MO and NAP were investigated via adsorption kinetics, isotherms, thermodynamics, and microstructural characterization. The maximum adsorption capacity of MO and NAP could reach 380.2 and 43.7 mg·g −1 at 298 K, respectively. The kinetic studies illustrated that the adsorption equilibria reached in 2 and 1 h for MO and NAP, respectively. The adsorption isotherms indicated that HMA-LDH fitted the Langmuir model toward MO removal, while partition model for NAP. The comparative mechanism between MO and NAP were determined by X-ray diffraction (XRD), Fourier transform spectroscopy (FTIR), and X-ray photoelectron spectroscopy (XPS). Anion exchange dominated the MO adsorption, whereas partition was deemed as the predominated mechanism for NAP. Furthermore, the recycle performance stated that HMA-LDH could be reused in five cycles in MO adsorption, while failed after two cycles for NAP. This study provided a theoretical foundation for the practical application of hierarchical flower-like LDH in the adsorption of persistent organic pollutants in the aquatic environment.

研究领域: 环境科学 · 材料科学
✓ 已验证 DOI 高影响因子
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION · 2023 ·Vol. 62 ·期 50 ·e202315911 · IF 16.6

Naphthyl Substituted Impurities Induce Efficient Room Temperature Phosphorescence

Weiguo Qiao,Ming Yao,Jingwen Xu,Haiyan Peng,Jianlong Xia,Xiaolin Xie,Zhong'an Li

Graphical The origin of yellow-green room temperature phosphorescence (RTP) of triphenylamine from commercial sources has been clarified for the first time, which inspires a general and convenient approach to construct bicomponent host/guest organic RTP materials, that is, doping naphthyl substituted analogues into the host molecule. Accidentally, it was found that triphenylamine (TPA) from commercial sources shows ultralong yellow-green room temperature phosphorescence (RTP) like commercial carbazole, which however disappears for lab-synthesized TPA with high purity. Herein, we for the first time identify the impurity types that cause RTP of commercial TPA, which are two N , N -diphenyl-naphthylamine isomers. Due to similar molecular polarity and very trace amount (≈0.8 ‰, molar ratio), these naphthyl substituted impurities can be easily overlooked. We further show that even at an extremely low amount (1000000 : 1, mass ratio) of impurities, RTP emission is still generated, attributed to the triplet-to-triplet energy transfer mechanism. Notably, this doping strategy is also applicable to the triphenylphosphine and benzophenone host systems, of which strong RTP emission can be activated by simply doping the corresponding naphthyl substituted analogues into them. This work therefore provides a general and efficient host/guest strategy toward high performance and diverse organic RTP materials.

研究领域: 材料科学 · 光学
✓ 已验证 DOI 高影响因子
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INORGANICA CHIMICA ACTA · 2020 · IF 2.304

Synthesis, crystal structures and photo-thermal properties of five naphthyl-functionalized Copper(II) coordination compounds

Hao-Hai Wang,Jing-Zhe Li,Jing Nie,Zi-Xuan Yao,Hong-Jing Li,Kuan-Guan Liu,Xiao-Wei Yan

For achieving solar absorber and conversion molecular materials with excellent photothermal conversion ability, five mononuclear Copper(II) coordination compounds have been designed and isolated. They are fully characterized by IR, Powder XRD, Solid-state UV, and TGA. Single-crystal X-ray structural analysis reveals that they are typical photothermal conversion molecules with double chromophores: one antenna chromophore (NT group here) and the second chromophores (Cu(dmap) 4 2+ , Cu(dmap) 2 2+ , Cu(bpy) 2 2+ and Cu(phen) 2 2+ ). Both chromophores have great influence on their solid-state optical absorption. Their photothermal conversion experiments show that compounds 3 , 4 and 5 have the better results (the highest temperature increment 21.7 ℃ and equilibrium temperature ~ 60.7 ℃) than compounds 1 and 2 . Those results give some clues for illustrating the molecular mechanisms of solar absorber and photothermal conversion molecular materials.

研究领域: 无机化学 · 材料科学
✓ 已验证 DOI 高影响因子
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TALANTA · 2023 · IF 6.1

Ammonium determination by merging-zone flow injection analysis and a naphthalene-based fluorescent probe

Xuejia Chen,Min Zhang,Xuejun Li,Jin Xu,Ying Liang

This paper discusses the first-time study of a naphthalene-based fluorescent probe—naphthalene-2,3-dicarboxaldehyde (NDA), in combination with merging-zone flow injection analysis for the automated fluorescence determination of ammonium. The determination was contingent on detecting the fluorescent product of NDA-SO 3 2- -NH 4 + , which has maximum excitation and emission wavelengths of 508 nm and 564 nm, respectively. And the possible sensing mechanism of NDA-NH 4 + was proposed. The effects of the reaction parameters, including reagent concentrations, reaction flow rate , coil length, reaction temperature, and pH were optimized. Under optimal conditions, this method afforded a sampling rate of 8 h −1 , a limit of detection of 0.045 μmol L −1 , and RSD of 3.68% (n = 14) with 1.50 μmol L −1 ammonium, and the calibration range was 0.045–6.00 μmol L −1 . Examination of the organic nitrogen interference confirmed that the method attracts minimal interference from organic nitrogen, and the stability of the NDA reagent facilitates its field application. Other exhibited advantages include low reagent consumption and high automation; the method has been utilized in the successful determination of ammonium in freshwater and rainwater. The development of NDA applications for ammonium determination also provides more options for fluorometric determination of ammonium.

研究领域: 环境科学 · 分析化学
✓ 已验证 DOI PubMed 高影响因子
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Journal of the Iranian Chemical Society · 2023 ·Vol. 20 ·期 11 ·2703-2712 · IF 2.4

A 3-position modified naphthalimide fluorescent probe for reversible response to H2O2 and GSH and cell imaging

Zhang Chenglu,Nie Shiru,Ding Yanwei,Liu Chang,Zhang Yanpeng,Zhang Yang,Guo Jinghao

An “off–on–off” fluorescent probe NapEb for high selectivity and reversible response to H 2 O 2 and GSH was synthesized. Inspired by the role of GSH in the human body, the –Se–N– bond in ebselen was successfully used as the recognition site. The probe NapEb is sensitive (LOD = 8.4 µM) and fast for H 2 O 2 (within 200 s). It can be used not only for qualitative and quantitative detection of H 2 O 2 in real samples, but also has been successfully used for the imaging detection of H 2 O 2 in MCF-7 cells with good effect. Moreover, continuous fluorescence recognition of GSH has also achieved significant results, the process is reversible and can be repeated for 5 times. The experimental results show that satisfactory results can also be obtained by structural modification at the 3-position of naphthalimide.

研究领域: 生物化学 · 分析化学 · 医学检测
✓ 已验证 DOI 高影响因子
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MACROMOLECULAR RAPID COMMUNICATIONS · 2020 ·Vol. 41 ·期 13 ·2000123 · IF 4.886

Naphthalimide-Based Aggregation-Induced Emissive Polymeric Hydrogels for Fluorescent Pattern Switch and Biomimetic Actuators

Hao Liu,Shuxin Wei,Huiyu Qiu,Beibei Zhan,Qingquan Liu,Wei Lu,Jiawei Zhang,To Ngai,Tao Chen

Substituted naphthalimide (NI) moieties are highly versatile and newly recognized aggregation-induced emission (AIE) building blocks for many potentially useful smart molecules, polymers, and nanoparticles. However, the introduction of NI fluorophore into cross-linked polymeric networks to prepare AIE-active hydrogels still remains underdeveloped. Herein, a novel naphthalimide-based aggregation-induced emissive polymeric hydrogel is reported, followed by its proof-of-concept applications as fluorescence pattern switch and biomimetic actuator. The hydrogel, bearing semi-interpenetrating polymer networks, is synthesized starting from N -isopropylacrylamide, hydroxyethyl methacrylate, and a newly designed NI monomer (4-phenoxy- N -allyl-1,8-naphthalimide, PhAN). Rational molecular design for AIE-active PhAN monomer lies in modification of the NI core with rigid and bulky phenoxy group to break its planarity to produce desirable propeller-shaped molecular conformation. The as-prepared hydrogel is proved to be a aggregation-induced blue-light-emitting hydrogel. It also shows volume phase transition behavior and is endowed with thermally responsive synergistic emission and transmittance change, thus enabling simultaneous regulation of two optical properties merely by one single stimulus. These useful advantages further encourage fabrication of several proto-type fluorescence pattern switching and biomimetic actuating devices. This study may not only enlarge the list of fluorescent hydrogels but also serve as a novel smart optical platform for potential anticounterfeiting, sensing, displaying, or actuating applications.

研究领域: 材料科学 · 化学 · 生物医学工程
✓ 已验证 DOI 高影响因子
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