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

Chinese Chemical Letters 2024年第1期35卷 361-365页

作者： Jin Li Qinglong Qiao Ning Xu Wei Zhou Jingli Yuan Zhaochao Xu State Key Laboratory of Fine Chemicals School of ChemistryDalian University of TechnologyDalian 116024China CAS Key Laboratory of Separation Science for Analytical Chemistry Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian 116023China University of Chinese Academy of Sciences Beijing 100049China

White light emitting systems of pure organic materials have attracted extensive research interest due to their better compatibility and functional *** 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 *** 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,*** 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 *** 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.

关键词： White light ESPT Hydrogen bond naphthalimide Double emission

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naphthalimide BASED DISPERSE DYES FOR NYLON 6 AND POLYESTER(PET) FIBERS:SYNTHESIS AND EVALUATION OF TECHNICAL PROPERTIES IN THE PRESENCE OF UREA

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Chinese Journal of Polymer Science 2011年第6期29卷 712-718页

作者： Javad Mokhtari Mahdi Nouri Uranus Goudarzi Department of Textile Engineering Faculty of EngineeringUniversity of GuilanRashtIran

Technical properties of two naphthalimide based disperse dyes on nylon 6 and polyester fibers were investigated in the presence of urea. The two naphthalimide based disperse dyes were synthesized. The dyes were purified and then fully characterized using 1H-NMR, FTIR and melting point analysis. Dispersion of the dyes was prepared in water and applied on nylon 6 and PET fibers. The dyes offered good build-up properties on the substrates. In order to increase dye adsorption of the substrates, urea was added into the dyebath. By adding urea, the dye adsorption of polyester was increased significantly, while the increase of that of nylon 6 was not marked. The dyes showed good fastness properties on the substrates.

关键词： naphthalimide Nylon 6 Polyester Urea Disperse dye

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naphthalimide and quinoline derivatives as inhibitors for insect N-acetyl-β-D-hexosaminidase

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Chinese Chemical Letters 2019年第5期30卷 977-980页

作者： Huibin Yang Huitang Qi Tian Liu Xusheng Shao Qing Yang Xuhong Qian Shanghai Key Laboratory of Chemical Biology Institute of Pesticides and PharmaceuticalsSchool of PharmacyEast China University of Science and TechnologyShanghai 200237China State Key Laboratory of the Discovery and Development of Novel Pesticide Shenyang Sinochem Agrochemicals Research and Development Co.Ltd.Shenyang 110021China School of Life Science and Biotechnology Dalian University of TechnologyDalian 116024China

Insect chitinolyticβ-N-acetyl-D-hexosaminidase,such as OfHex1 from Ostrinia furnacalis,is a potential target for insecticide *** the known OfH ex1 inhibitors,Q2 is of great interest because it is the first non-carbohydrate *** this study,we designed and synthesized a series of Q2 derivatives by replacing the thiadiazole and naphthalimide groups and changing the linker *** 3 m showed the best inhibitory activity with a Kivalue of 0.34 mmol/L against OfHex1,which is about onequarter that of Q2(K_i=1.4 mmol/L).Compound 6 a showed the best inhibitory activity among the quinoline-containing derivatives(K_i=2.3 mmol/L).Molecular docking indicated that although 3 m,6 a,and Q2 binding the active pocket of OfHex1 in similar mode,compound 3 m engaged better than the other compounds in intermolecular interaction with OfH ex1.

关键词： Of Hex1 inhibitors Structure-activity relationship naphthalimide derivatives Quinoline derivatives Molecular docking

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naphthalimide-modified near-infrared cyanine dye with a large stokes shift and its application in bioimaging

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Chinese Chemical Letters 2017年第10期28卷 1979-1982页

作者： Di Wu Yuanzhi Shen Jianhua Chen Guotao Liu Haiyan Chen Jun Yin Key Laboratory of Pesticide and Chemical Biology Ministry of Education College of Chemistry Central China Normal University Department of Biomedical Engineering School of Engineering China Pharmaceutical University

Developing the novel fluorescent dyes with a larger Stokes shift is still a challenge in the research of fluorescence probes. In this work, a naphthalimide-modified near-infrared cyanine dye with an emission at 785 nm has been synthesized for lysosome-targeting imaging. This fluorescent dye showed a large Stokes shift（up to 165 nm） and favorable lysosome-targeting property, which facilitated it to be a potential candidate for studying of lysosomal functions. The result also indicated that the probe is a promising contrast agent for in vivo imaging in mouse models.

关键词： Cyanine naphthalimide Near-infrared Stokes shift Bioimaging

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Study of Linear and Nonlinear Optical Properties of Four Derivatives of Substituted Aryl Hydrazones of 1,8-naphthalimide

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Chinese Journal of Chemistry 2014年第3期32卷 205-211页

作者： Peiyang Gu Xufeng Xu Feng Zhou Tingting Zhao Gaojie Ye Gaoyan Liu Qinghua Xu Jianfeng Ge Qingfeng Xu Jianmei Lu Department of Polymer Science College of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhouJiangsu 215123China Department of Chemistry National University of Singapore3 Science Drive 3117543Singapore

Four 1,8-naphthalimide hydrazone molecules with different electron-donating groups have been applied in the study of linear and nonlinear optical(NLO)*** compounds showed strong green emission in *** NLO properties such as two-photon absorption(TPA)behavior with femtosecond laser pulses ca.800 nm and excited-state absorption(ESA)behavior with nanosecond laser pulses at 532 nm were *** 4 presented the largest two-photon cross section(550 GM)among them due to two factors:the conjugated length of compound 4 is the longest and the electron-donating ability of compound 4 is the *** from TPA behavior,compound 2 showed the best nonlinear absorption properties at 532 nm and its nonlinear absorption coef-ficient and third-order nonlinear optical susceptibilitiesχ^(3)were up to 1.41×10^(−10) MKS and 4.65×10^(−12) esu,*** the modification of the structure,the nonlinear optical properties of these compounds at differ-ent wavelengths(532 and 800 nm)were well *** great broad-band nonlinear optical properties indicate hy-drazones are good candidates for organic nonlinear optical absorption materials.

关键词： excited-state absorption(ESA) fluorescence naphthalimide nonlinear optical(NLO) two-photon absorption(TPA)

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Novel benzimidazole derived naphthalimide triazoles: synthesis, antimicrobial activity and interactions with calf thymus DNA

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Science China Chemistry 2015年第3期58卷 483-494页

作者： Yun-Lei Luo Kishore Baathulaa Vijaya Kumar Kannekanti Cheng-He Zhou Gui-Xin Cai Key Laboratory of Applied Chemistry of Chongqing Municipality Institute of Bioorganic & Medicinal Chemistry School of Chemistry and Chemical Engineering Southwest University Department of Chemistry Kakatiya University Indian Institute of Chemical Technology

A novel series of benzimidazole derived naphthalimide triazoles and some corresponding triazoliums have been successfully synthesized and characterized by 1H NMR, 13 C NMR, 1H-1H COSY, IR and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution. 2-Chlorobenzyl triazolium 8g and compound 9b with octyl group exhibited the best antibacterial activities among all the tested compounds, especially against S. aureus with inhibitory concentration of 2 μg/mL which was equipotent potency to Norfloxacin(MIC=2 μg/mL) and more active than Chloromycin(MIC=7 μg/mL). Triazoliums 8g and 8f bearing 3-fluorobenzyl moiety displayed the best antifungal activities(MIC=2-19 μg/mL) against all the tested fungal strains without being toxic to PC12 cell line within concentration of 128 μg/m L. Further investigations by fluorescence and UV-Vis spectroscopic methods revealed that the compound 8g could effectively intercalate into calf thymus DNA to form the 8g-DNA complex which could block DNA replication, exerting powerful antimicrobial activities.

关键词： naphthalimide benzimidazole triazole antibacterial antifungal calf thymus DNA

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Cytotoxic activity and DNA binding of naphthalimide derivatives with amino acid and dichloroacetamide functionalizations

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Chinese Chemical Letters 2014年第7期25卷 1087-1093页

作者： Ke-Rang Wang Feng Qian Xiao-Man Wang Guan-Hai Tan Rui-Xue Rong Zhi-Ran Cao Hua Chen Ping-Zhu Zhang Xiao-Liu Li Key Laboratory of Chemical Biology of Hebei Province College of Chemistry and Environmental ScienceHebei University Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education Hebei University Department of Immunology School of Basic Medical ScienceHebei University

A series of novel naphthalimide derivatives modified by amino acids and their dichloroacetamide derivatives at the 3-position have been synthesized. Their cytotoxic activities were preliminarily evaluated against He/a, A549 and K562 cells, which showed that the length of the side chains of the amino acids influenced the cytotoxic activities. Moreover, compound 7d showed a very good cytotoxic activity against A549 cells with an IC50 value of 4.78 μmol L-1, Furthermore, the UV-vis, fluorescence, and circular dichroism （CD） spectroscopies and thermal denaturation experiment indicated that compounds 6a, 6d and 7a, 7d, as DNA intercalators, exhibited binding affinities with calf-thymus DNA （Ct-DNA）.

关键词： naphthalimide Dichloroacetamide Cytotoxic activity DNA binding

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A Bioorthogonal-Activated Fluorescence Turn-On Probe Based on Nitrone-Modified 1,8-naphthalimide for Live-Cell Imaging

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Chinese Journal of Chemistry 2022年第2期40卷 209-214页

作者： Yu Teng Hong Yang Xiang Li Yongcheng Wang Dali Yin Yulin Tian State Key Laboratory of Bioactive Substances and Function of Natural Medicine Beijing Key Laboratory of Active Substances Discovery and Drugability EvaluationInstitute of Materia MedicaPeking Union Medical College and Chinese Academy of Medical Sciences1st Xian Nong Tan StreetBeijing 100050China

A nitrone-modified 1,8-naphthalimide was desig ned as a novel bioorthog on alactivated turn-on probe based on strain-promoted alkyne-nitrone cycloadditio n(SPANC).The bioorthog onal cycloadducts were subseque ntly tran sformed into fluoresce nt rearra nge-ment products by photo-accelerati on,which exhibited sign ificant fluoresce nee enhan ceme nt,large stokes shift,and high fluores-cence qua ntum *** calculati ons were performed to elucidate the fluoresce nee OFF-ON mecha *** fluoroge nic strategy was successfully applied to labeling of proteins and visualizing mitochondria in live cells in real time.

关键词： Bioorthogonal reaction Fluorescence naphthalimide Imaging agents Cycloaddition

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A hydrophilic fluorescent polymer containing naphthalimide moiety as chemosensor for microbioreactors

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Science China Chemistry 2009年第6期52卷 821-826页

作者： SHEN LiangJun ZHU WeiHong MENG XianLe GUO ZhiQian TIAN He Key Laboratory for Advanced Materials and Institute of Fine Chemicals(Ministry of Education) East China University of Science and TechnologyShanghai 200237China

A novel hydrophilic copolymer P(NI-HEMA) containing the pendant group of naphthalimide moiety has been prepared. In the aqueous buffer solution, its film on the glass substrate shows an obvious fluorescence change and excellent linear relevance in the pH range of 5.8-8.0. Specifically, using the isobestic point at 406 nm as excitation wavelength can avoid the UV irradiation and the tedious calibration process. The film stability and hydrophilicity of copolymer P(NI-HEMA) were studied. Because of the easy synthesis, low price and high linear relevance to pH, the hydrophilic chemosensor film of P(NI- HEMA) could be potentially applied as a low-cost pH indicator for high-throughput bioprocessing in microreactors.

关键词： copolymer naphthalimide pH chemosensor hydrophilic

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Highly sensitive and selective ratiometric fluorescent copper sensors: Different binding affinities modulated by three separate side chains of naphthalimide

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Science China Chemistry 2009年第6期52卷 771-779页

作者： XU YuFang LU Feng XU ZhaoChao CHENG TanYu QIAN XuHong Shanghai Key Laboratory of Chemical Biology School of PharmacyEast China University of Science and TechnologyShanghai 200237China

A series of compounds 1-11 with different side chains of naphthalimide as fluorescent copper sensors were designed and synthesized. Compounds 1, 9, 10 and 11 presented a high selectivity to Cu2+ in a neutral aqueous environment. Here 1, 9 and 10 showed selectivity and affinity to Cu2+ with an association constant of about ～106. It gave somewhat response to Ag+, Co2+, Ni2+ and Fe2+ while 1 detected copper. 9 and 10 displayed better selectivity by changing their hydrophobic side chains to the hydrophilic ones on imide moieties. 11, with one flexible side chain, showed high selectivity and an association constant (Ka = 2.2 × 108), which were much higher than those of 1, 9 and 10. These results indicated that the selectivity and affinity could be improved by changing side chains of naphthalimide. That might provide a novel strategy or method for the development of fluorescent sensors.

关键词： Cu2+ fluorescence sensor complexation naphthalimide

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