In this review, we retrospect our progress in biological active naphthalimide and analogues as antitumor agents in the past 20 years. On one hand, various derivations in naphthalimide pharmacophores were developed to ...In this review, we retrospect our progress in biological active naphthalimide and analogues as antitumor agents in the past 20 years. On one hand, various derivations in naphthalimide pharmacophores were developed to enhance their DNA binding affinity and antitumor property thereby. Heterocyclic fused naphthalimides, bis-naphthalimides, non-fused substituted naphthalimides and the carboxamide derivatives were synthesized. For example, thio-heterocyclic fused-naphthalimides were designed and evaluated in comparison with their oxo-heterocyclic fused analogues. Extended or created heterocyclebased skeleton were also developed as antitumor agents. On the other hand, we broaden the design strategy of naphthalimide antitumor agents besides DNA intercalation and topo II poison. We have introduced more drug design methods, such as prodrugs, multitarget drugs, computer-aided drug design,photodynamic therapy. For example, we have got naphthalimide derivatives which inhibited topo II and induced LMP by introducing long alkyl chain and polyamines. Several representative compounds were clarified of their antitumor mechanism of action. In all, our research improves the structure diversity of naphthalimide antitumor agents and distinct variances of antitumor targets and mechanism of action.展开更多
To address the lack of systematic studies on heavy metal fluorescent probes in typical buffer solutions,this study developed a Fe^(3+)and Cu^(2+)fluorescent probe,DHU‑NP‑4,based on a naphthalimide fluorophore.Comparat...To address the lack of systematic studies on heavy metal fluorescent probes in typical buffer solutions,this study developed a Fe^(3+)and Cu^(2+)fluorescent probe,DHU‑NP‑4,based on a naphthalimide fluorophore.Comparative analysis of the probe's performance in various buffer systems revealed that buffers with high organic content are unsuitable for evaluating such probes.Furthermore,the pH of the solvent system was found to significantly influence the probe's behavior.Under highly acidic conditions(pH≤2),DHU‑NP‑4 exhibited exceptional specificity for Fe^(3+),while in alkaline conditions,it demonstrated high specificity for Cu^(2+).Leveraging these properties,the probe enabled the quantitative detection of Fe^(3+)and Cu^(2+)in solution.展开更多
A highly sensitive zinc ion fiuorescent probe NOD-NY with controlled release of nitric oxide was designed,synthesized and used for tracking intracellular zinc ions in living A549 cells.NOD-NY was prepared from naphtha...A highly sensitive zinc ion fiuorescent probe NOD-NY with controlled release of nitric oxide was designed,synthesized and used for tracking intracellular zinc ions in living A549 cells.NOD-NY was prepared from naphthalimide as the fiuorophore and N,N-bis(2-pyridylmethyl)amine as the zinc ion recognition receptor,the amide N atom of the naphthalimide was connected to n-butylamine.Under the irradiation of ultraviolet light,NOD-NY can quantitatively release nitric oxide and generate a highly sensitive zinc ion probe Zn-HN,accompanied by a red-shift process of maximum ultraviolet absorption from 350 nm to 450 nm.Upon addition of Zn^(2+)to the solutions of Zn-HN,a remarkable fiuorescence enhancement was observed,which could be attributed to the photo-induced electron transfer(PET)mechanism.By replaced the nbutylamine on NOD-NY with diethylene glycolamine or triphenylphosphine structures,NOD-AY with good biocompatibility and NOD-BY that can target mitochondria were obtained respectively.In addition,the nitric oxide released by NOD-NY enriched in lysosome can diffuse into mitochondria.The released nitric oxide can stimulate metallothionein to release zinc ions,and the light-induced in situ generated zinc ion probe Zn-HN can have a highly sensitive fiuorescence response to free zinc ions in living A549 cells.展开更多
Temperature plays a crucial role in regulating polymorphism in supramolecular polymers.Understanding the mechanism behind temperature-dependent supramolecular polymorphism is crucial as it provides an opportunity to t...Temperature plays a crucial role in regulating polymorphism in supramolecular polymers.Understanding the mechanism behind temperature-dependent supramolecular polymorphism is crucial as it provides an opportunity to tailor polymorphs for specific properties and applications.In this study,we present our findings on a naphthalimide-substituted benzene-1,3,5-tricarboxamide derivative,R-Nap-1,which exhibits two distinct polymerization pathways at varying temperatures.At 313 K,polymerization results in the formation of an M-chiral polymorph,whereas at 253 K,a P-chiral polymorph is formed.Both polymorphs are notably stable,remaining unchanged for over six months under ambient conditions.Theoretical calculations and experimental investigations allowed us to elucidate the mechanisms underlying these polymorphic transformations.The formation of the M-chiral polymorph at 313 K is attributed to the nucleation and growth of R-Nap-1 monomers once their concentration surpasses a critical threshold.Conversely,at lower temperatures(e.g.,253 K),the monomers undergo facile transformation into dimers due to a lower energy barrier and reduced Gibbs energy compared to the monomeric state.Subsequently,these dimers undergo nucleation-elongation to form the P-chiral polymorph when their concentration exceeds the critical polymerization concentration.The stability and lack of interconversion between the two polymorphs can be attributed to their close thermodynamic stabilities,as evidenced by variable-temperature CD spectra and DFT calculations.These findings highlight the importance of accurate temperature control in supramolecular polymerization processes,making a significant contribution to the understanding of supramolecular polymorphism,thus advancing the field of supramolecular chemistry.展开更多
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 base...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.展开更多
Understanding the role of perovskite surface passivators in hot carriers transfer dynamics is important to develop highly efficient perovskite solar cells(PSCs).In this work,we have designed and synthesized a naphthal...Understanding the role of perovskite surface passivators in hot carriers transfer dynamics is important to develop highly efficient perovskite solar cells(PSCs).In this work,we have designed and synthesized a naphthalimide-based organic small molecule(NCN)for perovskite surface defect passivator.We reveal that the introduction of NCN not only reduces the density of perovskite defect-state,but also promotes hot carriers(HCs)cooling in perovskite through the transient absorption spectroscopy measurements.Fast HCs cooling permits HCs transfer from perovskite layer into NCN layer,thus resulting in the decreased charge-carrier recombination in NCN-treated device.As expected,the power conversion efficiency(PCE)of PSCs with NCN is enhanced to 22.02%from 19.95%for the control device.The findings are relevant for developing highly efficient PSCs.展开更多
Two new diarylamine-substituted 1, 8-naphthalimide derivatives are synthesized by Cu I/18-crown-6/K2CO3 catalyst system and characterized by Fourier transform infrared （FT- IR）, ^1H-NMR and elemental analyses. The U...Two new diarylamine-substituted 1, 8-naphthalimide derivatives are synthesized by Cu I/18-crown-6/K2CO3 catalyst system and characterized by Fourier transform infrared （FT- IR）, ^1H-NMR and elemental analyses. The UV-vis absorption and photoluminescent （PL）spectra of the systems in n-hexane, tetrahydrofuran（THF）, and CH2Cl2 are investigated. These naphthalimide molecules have an absorption band centered at about 450 nm, which is assigned to an intramolecular chargetransfer （ICT）transition, and they emit light at 492, 501 nm in a nonpolar solvent such as n-hexane, and at 600, 620 nm in a polar solvent such as CH2Cl2. From the Lippert-Mataga equation, the difference of the dipole moment between the excited state and the ground state is estimated to be 9.2 and 9.8 D for 4- （ diphenylamine ）-N-（ 2-methoxyphenyl ）-1, 8-naphthalimide （ DMN-1 ） and 4-（ 2-naphthylphenylamine ）-N-（ 2- methoxyphenyl）-1, 8-naphthalimide （DMN-2）, respectively. This large change in the dipole moment upon excitation is typical for photoinduced ICT processes.展开更多
Understanding the physical mechanisms governing aggregation-induced-emission(AIE)and aggrega-tion-caused-quenching plays a vital role in developing functional AIE materials.In this work,tetraphenylethene(TPE,a classic...Understanding the physical mechanisms governing aggregation-induced-emission(AIE)and aggrega-tion-caused-quenching plays a vital role in developing functional AIE materials.In this work,tetraphenylethene(TPE,a classical AiEgen)and naphthalimide(NI,a popular fluorophore with ACQ characteristics)were connected through non-conjugated linkages and conjugated linkages.We showed that the nonconjugated-linkage of TPE to NI fragments leads to substantial PET in molecular aggregates and ACQ.In con trast,the conjugated conn ection between TPE and NI moieties results in the AIE phenomenon by suppressing twisted intramolecular charge transfer.This work provides an important guideline for the rational design of AIE materials.展开更多
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...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.展开更多
A polarity-sensitive fluorescent probe MNP was rationally designed and synthesized with naphthalimide as the fluorophore and maleimide as the receptor for thiols. MNP is weakly fluorescent due to the photoinduced elec...A polarity-sensitive fluorescent probe MNP was rationally designed and synthesized with naphthalimide as the fluorophore and maleimide as the receptor for thiols. MNP is weakly fluorescent due to the photoinduced electron-transfer （PET） from the fluorophore to the receptor, and it displays evidently solvatochromic UV-vis and fluorescence spectra： the emission shifted from 495 nm in n-hexane to 545 nm in phosphate buffer solution. Michael addition reaction between thiols and the maleimide in MNP inhibited the PET process, which led to about eight-fold fluorescence enhancement. In addition, MNP showed highly sensitivity to rnercapto-containing proteins and it could detect as low as 20.4 μg/mL of BSA in PBS. MNP has potential in fluorescent imaging of thiols in living cells.展开更多
Iron is one of the essential trace elements in the human body.It plays an important role in human biology and pathology.Deregulation of iron levels in cells is associated with disease development.In this work,we synth...Iron is one of the essential trace elements in the human body.It plays an important role in human biology and pathology.Deregulation of iron levels in cells is associated with disease development.In this work,we synthesized a novel near-infrared intramolecular charge transfer(ICT)based ratiometric fluorescent probe to detect Fe^(2+),by using naphthalimide and indole moieties as building blocks.Our work showed that the radiometric probe has excellent selectivity,sensitivity and rapid response.Moreover,we could successfully perform real-time monitoring of Fe^(2+) in He La cells and C.elegans.展开更多
Novel perylene bisimide dyes bay-functionalized with naphthalimide chromophores have been prepared conveniently by coupling of 1,8-naphthalimide and dibromoperylene bisimides. Their optical properties were investigate...Novel perylene bisimide dyes bay-functionalized with naphthalimide chromophores have been prepared conveniently by coupling of 1,8-naphthalimide and dibromoperylene bisimides. Their optical properties were investigated by UV-vis and fluorescence spectroscopy. The absorption spectra of these compounds showed wide spectral responses from 300 to 700 nm, which would be potentials for application as organic solar cells.展开更多
Two kinds of fluorescent nano-probes（pH-A and pH-B） with different diameters for the determination of H＋concentration, based on photo-induced electron transfer mechanism, were synthesized through click reaction. In...Two kinds of fluorescent nano-probes（pH-A and pH-B） with different diameters for the determination of H＋concentration, based on photo-induced electron transfer mechanism, were synthesized through click reaction. In which 1,8-naphthalimide was employed as the fluorophore and N,N-dimethylethylenediamine as the receptor. The effects of particle size and linker length on the photophysical properties of the probe were studied. The results revealed that the nano-probes were more sensitive toward pH with increasing particle size. The fluorescence intensity at 529 nm（I529） of the nano-probe p H-A of 120 nm exhibited good linear relationship with solution＇s pH in the range of 6–8. The probe p H-A displayed excellent selectivity and competition toward proton over other possible coexisted ions, and it could be applied to detect pH in realistic samples（river water, urine）.展开更多
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 purifi...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.展开更多
A novel series of calix[4]azacrown derivatives with the reaction between calix[4]azacrown and the different fluorophore derivatives,which may be useful fluorescent receptors,have been synthesized and structurally char...A novel series of calix[4]azacrown derivatives with the reaction between calix[4]azacrown and the different fluorophore derivatives,which may be useful fluorescent receptors,have been synthesized and structurally characterized by IR,~1H NMR,^（13）C NMR and MS.From their analysis data,it was found those compounds adopted a cone conformation.展开更多
A novel alkynyl substituted N-aryl-1,8-naphthalimide II （C20H11NO2） was synthesized for the discovery and evaluation of new fluorescence probes, and was characterized by X-ray crystal diffraction. It crystallizes in...A novel alkynyl substituted N-aryl-1,8-naphthalimide II （C20H11NO2） was synthesized for the discovery and evaluation of new fluorescence probes, and was characterized by X-ray crystal diffraction. It crystallizes in monoclinic, space group P21/n with a = 15.898（3）, b = 5.0102（10）, c = 17.962（4）A, β = 92.97（3）°, V = 1428.7（5） A^3, Z = 4, Mr = 297.30, Dc = 1.382 g/cm^3, F（000） = 616,/J = 0.090 mm^-1, S = 1.011, the final R = 0.0542 and wR = 0.1204 for 1669 observed reflections with I 〉 2σ（I） and 212 variable parameters. Hydrogen-bounding and n-stacking interactions were discussed. The influence of acetylene group on the fluorescence properties was also investigated. In comparison with N-phenyl-1,8-naphthalimide I （C18H11NO2）, few new structure characters and fluorescence properties of the title compound have been found.展开更多
A new benzoimidazole-naphthalimide derivative 4 was synthesized and its photophysical properties were studied. This compound showed highly selectively and sensitive colorimetric and ratiometric sensing ability for flu...A new benzoimidazole-naphthalimide derivative 4 was synthesized and its photophysical properties were studied. This compound showed highly selectively and sensitive colorimetric and ratiometric sensing ability for fluoride anion.展开更多
Zinc plays a significant role in oxidative balance and central nervous systems. Herein, we reported a highly sensitive fluorescent probe DR, bearing a morpholine group and a BPEN ligand in the naphthalimide fluorophor...Zinc plays a significant role in oxidative balance and central nervous systems. Herein, we reported a highly sensitive fluorescent probe DR, bearing a morpholine group and a BPEN ligand in the naphthalimide fluorophore. Upon Zn2+binding, DR exhibited remarkable fluorescence enhancement, and showed high sensitivity to Zn2+with the association constant of 4.9 ? 108 L/mol, and the detection limit of15 nmol/L. Confocal imaging experiments indicated that DR was able to localize to lysosomes in MCF-7 cells. Moreover, upon H2 O2 stimulation in SH-SY5 Y cells, endogenous release of Zn2+was observed.展开更多
Insect chitinolyticβ-N-acetyl-D-hexosaminidase,such as OfHex1 from Ostrinia furnacalis,is a potential target for insecticide design.Among the known OfH ex1 inhibitors,Q2 is of great interest because it is the first n...Insect chitinolyticβ-N-acetyl-D-hexosaminidase,such as OfHex1 from Ostrinia furnacalis,is a potential target for insecticide design.Among the known OfH ex1 inhibitors,Q2 is of great interest because it is the first non-carbohydrate inhibitor.In this study,we designed and synthesized a series of Q2 derivatives by replacing the thiadiazole and naphthalimide groups and changing the linker length.Compound 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.展开更多
Herein we presented a general strategy for in situ assembly of intramolecular charge-transfer(ICT)-based light-up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling reaction.By introducing iodo group at the ...Herein we presented a general strategy for in situ assembly of intramolecular charge-transfer(ICT)-based light-up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling reaction.By introducing iodo group at the appropriate position,five fluorophores with different scaffolds including naphthalimide,coumarin,naphthalene sulfonate,nitrobenzoxadiazole,and acetonaphthone,were designed as bioorthogonal multicolor fluorogenic probes,which could produce significant fluorescence enhancement and high fluorescence quantum yield after Suzuki-Miyaura reaction with aryl boronic acid or boronate.Manipulating the substituents andπscaffold in the fluorophores allows fine-tuning of their photophysical properties.With this strategy,we succeeded in peptide conjugation,no-wash fluorogenic protein labeling,and mitochondria-selective bioorthogonal imaging in live cells.展开更多
基金the financial supports from the National Natural Science Foundation of China(No.20536010)National Key Project for Basic Research(No.2003CB114400)the Program of Shanghai Subject Chief Scientist and the Science and Technology Foundation of Shanghai
文摘In this review, we retrospect our progress in biological active naphthalimide and analogues as antitumor agents in the past 20 years. On one hand, various derivations in naphthalimide pharmacophores were developed to enhance their DNA binding affinity and antitumor property thereby. Heterocyclic fused naphthalimides, bis-naphthalimides, non-fused substituted naphthalimides and the carboxamide derivatives were synthesized. For example, thio-heterocyclic fused-naphthalimides were designed and evaluated in comparison with their oxo-heterocyclic fused analogues. Extended or created heterocyclebased skeleton were also developed as antitumor agents. On the other hand, we broaden the design strategy of naphthalimide antitumor agents besides DNA intercalation and topo II poison. We have introduced more drug design methods, such as prodrugs, multitarget drugs, computer-aided drug design,photodynamic therapy. For example, we have got naphthalimide derivatives which inhibited topo II and induced LMP by introducing long alkyl chain and polyamines. Several representative compounds were clarified of their antitumor mechanism of action. In all, our research improves the structure diversity of naphthalimide antitumor agents and distinct variances of antitumor targets and mechanism of action.
文摘To address the lack of systematic studies on heavy metal fluorescent probes in typical buffer solutions,this study developed a Fe^(3+)and Cu^(2+)fluorescent probe,DHU‑NP‑4,based on a naphthalimide fluorophore.Comparative analysis of the probe's performance in various buffer systems revealed that buffers with high organic content are unsuitable for evaluating such probes.Furthermore,the pH of the solvent system was found to significantly influence the probe's behavior.Under highly acidic conditions(pH≤2),DHU‑NP‑4 exhibited exceptional specificity for Fe^(3+),while in alkaline conditions,it demonstrated high specificity for Cu^(2+).Leveraging these properties,the probe enabled the quantitative detection of Fe^(3+)and Cu^(2+)in solution.
基金the National Natural Science Foundation of China(Nos.21878088,21476077)Key projects of Shanghai Science and Technology Commission(No.18DZ1112703)Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism(Shanghai Municipal Education Commission,No.2021 Sci&Tech 03–2)for financial support。
文摘A highly sensitive zinc ion fiuorescent probe NOD-NY with controlled release of nitric oxide was designed,synthesized and used for tracking intracellular zinc ions in living A549 cells.NOD-NY was prepared from naphthalimide as the fiuorophore and N,N-bis(2-pyridylmethyl)amine as the zinc ion recognition receptor,the amide N atom of the naphthalimide was connected to n-butylamine.Under the irradiation of ultraviolet light,NOD-NY can quantitatively release nitric oxide and generate a highly sensitive zinc ion probe Zn-HN,accompanied by a red-shift process of maximum ultraviolet absorption from 350 nm to 450 nm.Upon addition of Zn^(2+)to the solutions of Zn-HN,a remarkable fiuorescence enhancement was observed,which could be attributed to the photo-induced electron transfer(PET)mechanism.By replaced the nbutylamine on NOD-NY with diethylene glycolamine or triphenylphosphine structures,NOD-AY with good biocompatibility and NOD-BY that can target mitochondria were obtained respectively.In addition,the nitric oxide released by NOD-NY enriched in lysosome can diffuse into mitochondria.The released nitric oxide can stimulate metallothionein to release zinc ions,and the light-induced in situ generated zinc ion probe Zn-HN can have a highly sensitive fiuorescence response to free zinc ions in living A549 cells.
基金supported by the Chinese Academy of Sciences CAS Project for Young Scientists in Basic Research(No.YSBR-027)。
文摘Temperature plays a crucial role in regulating polymorphism in supramolecular polymers.Understanding the mechanism behind temperature-dependent supramolecular polymorphism is crucial as it provides an opportunity to tailor polymorphs for specific properties and applications.In this study,we present our findings on a naphthalimide-substituted benzene-1,3,5-tricarboxamide derivative,R-Nap-1,which exhibits two distinct polymerization pathways at varying temperatures.At 313 K,polymerization results in the formation of an M-chiral polymorph,whereas at 253 K,a P-chiral polymorph is formed.Both polymorphs are notably stable,remaining unchanged for over six months under ambient conditions.Theoretical calculations and experimental investigations allowed us to elucidate the mechanisms underlying these polymorphic transformations.The formation of the M-chiral polymorph at 313 K is attributed to the nucleation and growth of R-Nap-1 monomers once their concentration surpasses a critical threshold.Conversely,at lower temperatures(e.g.,253 K),the monomers undergo facile transformation into dimers due to a lower energy barrier and reduced Gibbs energy compared to the monomeric state.Subsequently,these dimers undergo nucleation-elongation to form the P-chiral polymorph when their concentration exceeds the critical polymerization concentration.The stability and lack of interconversion between the two polymorphs can be attributed to their close thermodynamic stabilities,as evidenced by variable-temperature CD spectra and DFT calculations.These findings highlight the importance of accurate temperature control in supramolecular polymerization processes,making a significant contribution to the understanding of supramolecular polymorphism,thus advancing the field of supramolecular chemistry.
基金the National Natural Science Foundation of China(Nos.22225806,22078314,22278394)Dalian Institute of Chemical Physics(Nos.DICPI202227,DICPI202142).
文摘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.
基金High-Level Talents Introduction in Yunnan Province(No.C619300A010)the Fund for Excellent Young Scholars of Yunnan(No.202001AW070008)+5 种基金Spring City Plan:the High-level Talent Promotion and Training Project of Kunming(No.2022SCP005)for financial supportsupport from the Postdoctoral Foundation of Department of Human Resources and Social Security of Yunnan Province(No.C615300504046)Postdoctoral Research Foundation of Yunnan University(No.W8223004)the National Natural Science Foundation of China(No.22209144)the Project of Natural Science Foundation of Yunnan(Nos.202101AU070034 and 202101AT070337)the Innovation and Entrepreneurship Training Program for college students(No.202110673032)。
文摘Understanding the role of perovskite surface passivators in hot carriers transfer dynamics is important to develop highly efficient perovskite solar cells(PSCs).In this work,we have designed and synthesized a naphthalimide-based organic small molecule(NCN)for perovskite surface defect passivator.We reveal that the introduction of NCN not only reduces the density of perovskite defect-state,but also promotes hot carriers(HCs)cooling in perovskite through the transient absorption spectroscopy measurements.Fast HCs cooling permits HCs transfer from perovskite layer into NCN layer,thus resulting in the decreased charge-carrier recombination in NCN-treated device.As expected,the power conversion efficiency(PCE)of PSCs with NCN is enhanced to 22.02%from 19.95%for the control device.The findings are relevant for developing highly efficient PSCs.
基金The Ph.D.Programs Foundation of Ministry of Educa-tion of China(No.20030286012)the High Technology Research and De-velopment Program of Jiangsu Province(No.BG2005034)
文摘Two new diarylamine-substituted 1, 8-naphthalimide derivatives are synthesized by Cu I/18-crown-6/K2CO3 catalyst system and characterized by Fourier transform infrared （FT- IR）, ^1H-NMR and elemental analyses. The UV-vis absorption and photoluminescent （PL）spectra of the systems in n-hexane, tetrahydrofuran（THF）, and CH2Cl2 are investigated. These naphthalimide molecules have an absorption band centered at about 450 nm, which is assigned to an intramolecular chargetransfer （ICT）transition, and they emit light at 492, 501 nm in a nonpolar solvent such as n-hexane, and at 600, 620 nm in a polar solvent such as CH2Cl2. From the Lippert-Mataga equation, the difference of the dipole moment between the excited state and the ground state is estimated to be 9.2 and 9.8 D for 4- （ diphenylamine ）-N-（ 2-methoxyphenyl ）-1, 8-naphthalimide （ DMN-1 ） and 4-（ 2-naphthylphenylamine ）-N-（ 2- methoxyphenyl）-1, 8-naphthalimide （DMN-2）, respectively. This large change in the dipole moment upon excitation is typical for photoinduced ICT processes.
基金financial support from the National Natural Science Foundation of China (Nos.21676113,21772054)Distinguished Young Scholar Program of Hubei Province (No. 2018CFA079)+5 种基金the 111 Project B17019the Scholar Support Program of CCNU (No.0900-31101090002)the Excellent Doctoral Dissertation Cultivation Grant of CCNU from the colleges’ basic research and operation grant (MOE,No.2019YBZZ029)supported by Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules (No. KLSAOFM2012),Hubei University,Chinasupported by excellent doctorial dissertation cultivation grant of CCNU from the colleges’ basic research and operation of MOE (No.2019YBZZ029)A*STAR under its Advanced Manufacturing and Engineering Program (No.A2083c0051)
文摘Understanding the physical mechanisms governing aggregation-induced-emission(AIE)and aggrega-tion-caused-quenching plays a vital role in developing functional AIE materials.In this work,tetraphenylethene(TPE,a classical AiEgen)and naphthalimide(NI,a popular fluorophore with ACQ characteristics)were connected through non-conjugated linkages and conjugated linkages.We showed that the nonconjugated-linkage of TPE to NI fragments leads to substantial PET in molecular aggregates and ACQ.In con trast,the conjugated conn ection between TPE and NI moieties results in the AIE phenomenon by suppressing twisted intramolecular charge transfer.This work provides an important guideline for the rational design of AIE materials.
基金support from National Natural Science Foundation of China (Nos. 21676113, 21402057, 21472059, 81671803)Youth Chen-Guang Project of Wuhan (2016070204010098)+2 种基金the 111 Project B17019the Ministry Province Jointly Constructed Base for State Key Lab-Shenzhen Key Laboratory of Chemical Biology, Shenzhensupported by Self-determined Research Funds of CCNU from the colleges’ basic research and operation of MOE (No. CCNU16A02004)
文摘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.
基金financially supported by NSFC (Nos.21576085 and 21475044)Shanghai Municipal Natural Science Foundation (No.15ZR1409000)
文摘A polarity-sensitive fluorescent probe MNP was rationally designed and synthesized with naphthalimide as the fluorophore and maleimide as the receptor for thiols. MNP is weakly fluorescent due to the photoinduced electron-transfer （PET） from the fluorophore to the receptor, and it displays evidently solvatochromic UV-vis and fluorescence spectra： the emission shifted from 495 nm in n-hexane to 545 nm in phosphate buffer solution. Michael addition reaction between thiols and the maleimide in MNP inhibited the PET process, which led to about eight-fold fluorescence enhancement. In addition, MNP showed highly sensitivity to rnercapto-containing proteins and it could detect as low as 20.4 μg/mL of BSA in PBS. MNP has potential in fluorescent imaging of thiols in living cells.
基金the National Natural Science Foundation of China(Nos.21672185 and 21867019)the"Youth Talent of WanRen Project"Foundation of Yunnan Province of China for the financial support"LianDa Scholar Project"and"Graduate Research and Innovation"Foundation of Yunnan Normal University(No.Ysdyjs2019122)。
文摘Iron is one of the essential trace elements in the human body.It plays an important role in human biology and pathology.Deregulation of iron levels in cells is associated with disease development.In this work,we synthesized a novel near-infrared intramolecular charge transfer(ICT)based ratiometric fluorescent probe to detect Fe^(2+),by using naphthalimide and indole moieties as building blocks.Our work showed that the radiometric probe has excellent selectivity,sensitivity and rapid response.Moreover,we could successfully perform real-time monitoring of Fe^(2+) in He La cells and C.elegans.
基金This work was supported by National Natural Science Foundation of China and Shanghai Science Committee.
文摘Novel perylene bisimide dyes bay-functionalized with naphthalimide chromophores have been prepared conveniently by coupling of 1,8-naphthalimide and dibromoperylene bisimides. Their optical properties were investigated by UV-vis and fluorescence spectroscopy. The absorption spectra of these compounds showed wide spectral responses from 300 to 700 nm, which would be potentials for application as organic solar cells.
基金financial support from the National Natural Science Foundation of China (No. 21576085)
文摘Two kinds of fluorescent nano-probes（pH-A and pH-B） with different diameters for the determination of H＋concentration, based on photo-induced electron transfer mechanism, were synthesized through click reaction. In which 1,8-naphthalimide was employed as the fluorophore and N,N-dimethylethylenediamine as the receptor. The effects of particle size and linker length on the photophysical properties of the probe were studied. The results revealed that the nano-probes were more sensitive toward pH with increasing particle size. The fluorescence intensity at 529 nm（I529） of the nano-probe p H-A of 120 nm exhibited good linear relationship with solution＇s pH in the range of 6–8. The probe p H-A displayed excellent selectivity and competition toward proton over other possible coexisted ions, and it could be applied to detect pH in realistic samples（river water, urine）.
文摘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.
基金the National High Technology Research and Development Program 863(No. 2008AA03A315)The Research Fund for the Doctoral Program of High Education(No.20060056017).
文摘A novel series of calix[4]azacrown derivatives with the reaction between calix[4]azacrown and the different fluorophore derivatives,which may be useful fluorescent receptors,have been synthesized and structurally characterized by IR,~1H NMR,^（13）C NMR and MS.From their analysis data,it was found those compounds adopted a cone conformation.
基金supported by Tianjin Municipal Science and Technology Commission (09JCYBJC09200)National Key Basic Research and Development Program of China (973 Program, 2007CB914803)
文摘A novel alkynyl substituted N-aryl-1,8-naphthalimide II （C20H11NO2） was synthesized for the discovery and evaluation of new fluorescence probes, and was characterized by X-ray crystal diffraction. It crystallizes in monoclinic, space group P21/n with a = 15.898（3）, b = 5.0102（10）, c = 17.962（4）A, β = 92.97（3）°, V = 1428.7（5） A^3, Z = 4, Mr = 297.30, Dc = 1.382 g/cm^3, F（000） = 616,/J = 0.090 mm^-1, S = 1.011, the final R = 0.0542 and wR = 0.1204 for 1669 observed reflections with I 〉 2σ（I） and 212 variable parameters. Hydrogen-bounding and n-stacking interactions were discussed. The influence of acetylene group on the fluorescence properties was also investigated. In comparison with N-phenyl-1,8-naphthalimide I （C18H11NO2）, few new structure characters and fluorescence properties of the title compound have been found.
基金supported by National Basic Research 973 Program (No.2006CB806200) and Scientific Committee of Shanghai.
文摘A new benzoimidazole-naphthalimide derivative 4 was synthesized and its photophysical properties were studied. This compound showed highly selectively and sensitive colorimetric and ratiometric sensing ability for fluoride anion.
基金the National Natural Science Foundation of China (No. 21476077) for financial support
文摘Zinc plays a significant role in oxidative balance and central nervous systems. Herein, we reported a highly sensitive fluorescent probe DR, bearing a morpholine group and a BPEN ligand in the naphthalimide fluorophore. Upon Zn2+binding, DR exhibited remarkable fluorescence enhancement, and showed high sensitivity to Zn2+with the association constant of 4.9 ? 108 L/mol, and the detection limit of15 nmol/L. Confocal imaging experiments indicated that DR was able to localize to lysosomes in MCF-7 cells. Moreover, upon H2 O2 stimulation in SH-SY5 Y cells, endogenous release of Zn2+was observed.
基金the National Key Research and Development Program of China(Nos.2017YFD0200500,2017YFD0201400,2018YFD0200100)the National Natural Science Foundation of China(No.31871959)for the financial support
文摘Insect chitinolyticβ-N-acetyl-D-hexosaminidase,such as OfHex1 from Ostrinia furnacalis,is a potential target for insecticide design.Among the known OfH ex1 inhibitors,Q2 is of great interest because it is the first non-carbohydrate inhibitor.In this study,we designed and synthesized a series of Q2 derivatives by replacing the thiadiazole and naphthalimide groups and changing the linker length.Compound 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.
基金supported by the Beijing Nova Program(No.Z201100006820049)the National Natural Science Foundation of China(No.21907109)the CAMS Innovation Fund for Graduate Students(No.2019–1007–03)
文摘Herein we presented a general strategy for in situ assembly of intramolecular charge-transfer(ICT)-based light-up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling reaction.By introducing iodo group at the appropriate position,five fluorophores with different scaffolds including naphthalimide,coumarin,naphthalene sulfonate,nitrobenzoxadiazole,and acetonaphthone,were designed as bioorthogonal multicolor fluorogenic probes,which could produce significant fluorescence enhancement and high fluorescence quantum yield after Suzuki-Miyaura reaction with aryl boronic acid or boronate.Manipulating the substituents andπscaffold in the fluorophores allows fine-tuning of their photophysical properties.With this strategy,we succeeded in peptide conjugation,no-wash fluorogenic protein labeling,and mitochondria-selective bioorthogonal imaging in live cells.
