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
Antioxidants addition is believed as a facile and effective way to improve jet fuel thermal oxidation stability.However,amine antioxidants,as one of the most important antioxidants,have not received sufficient attenti...Antioxidants addition is believed as a facile and effective way to improve jet fuel thermal oxidation stability.However,amine antioxidants,as one of the most important antioxidants,have not received sufficient attention in the field of jet fuel autoxidation yet.Herein,the inhibition efficiency and mechanism of decane and exo-tetrahydrodicyclopentadiene(THDCPD)oxidation by di-4-tert-butylphenylamine(diarylamine)was experimentally and theoretically investigated.The results show that diarylamine can significantly inhibit decane oxidation but is less efficient for THDCPD oxidation,which is attributed to the higher energy barrier of retro-carbonyl-ene reaction(rate-determining step)in THDCPD than that in decane during diarylamine regeneration.However,the addition of diarylamine will cause undesirable color change after accelerated oxidation and produce slightly more deposits during high-temperature thermal oxidative stress for both decane and THDCPD.The results provide significant implications for the future design of effective antioxidant additives for high-performance jet fuel.展开更多
Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^（13） C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of th...Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^（13） C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani,Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC_（50） values of 0.013, 1.608 and 1.874 mg/m L, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC_（50） value of 22.21 mg/m L. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.展开更多
A series of dehydroabietic acid-based diarylamines have been synthesized in order to investigate their fluorescent properties, photostability, cell toxicity and in vitro fluorescence imaging. The geometries as well as...A series of dehydroabietic acid-based diarylamines have been synthesized in order to investigate their fluorescent properties, photostability, cell toxicity and in vitro fluorescence imaging. The geometries as well as their molecular properties were optimized at the B3LYP/6-31G~* level using Gaussian 03. The results indicate that molecular geometry, HOMO and LUMO energies, and energy gaps are important to predict absorption and fluorescent properties. Five of the compounds can be effectively taken up by human cervical carcinoma, human hepatocellular carcinoma SMMC-7721, human gastric cancer SGC-7901 and human lung adenocarcinoma A549 cells and strong blue fluorescent signals are detected in these cells. These compounds are potential candidates for fluorescent probes in biological diagnosis.展开更多
A mild one-step radical-to-radical synthetic strategy has been developed to directly produce a new family of diarylamine-substituted tris(2,4,6-trichlorophenyl)methyl(TTM)radicals TTM-DPA,TTM-DBPA,and TTM-DFA.The obta...A mild one-step radical-to-radical synthetic strategy has been developed to directly produce a new family of diarylamine-substituted tris(2,4,6-trichlorophenyl)methyl(TTM)radicals TTM-DPA,TTM-DBPA,and TTM-DFA.The obtained TTM radical derivatives are extremely stable during chromatography purification and long-term storage in the solid state.展开更多
In this work,4-substituted phenylacetylides with electron-rich N,N’-diarylamine groups are used for the design of triphosphine-supported PtAu_(2) complexes with red phosphorescence.Although PtAu_(2) complex 1 with 4-...In this work,4-substituted phenylacetylides with electron-rich N,N’-diarylamine groups are used for the design of triphosphine-supported PtAu_(2) complexes with red phosphorescence.Although PtAu_(2) complex 1 with 4-ethynyl-N,N’-diphenylaniline displays orange emission in CH_(2)Cl_(2) solution,highly efficient red phosphorescence is attained upon using 5-ethynyl-N,N’-diphenylthiophen-2-amine(2)or 2-ethynyl-4-phenyl-4H-dithieno[3,2-b:2’,3’-d]pyrrole(3)in place of 4-ethynyl-N,N-diphenylaniline(1).In contrast to the intense phosphorescence of complexes 1 and 3 in degassed CH_(2)Cl_(2) solution at ambient temperature,complex 2 shows a quite weak phosphorescence as well as fluorescence of the acetylide ligand due to incomplete energy transfer from acetylide ligands to PtAu_(2) centres.Since the phosphorescence efficiency of the doping films is as high as 98.3%,complexes 1–3 are excellent phosphorescent dopants in organic light-emitting diodes(OLEDs).Solution-processed OLEDs showed high-efficiency yellow emission for complex 1(λ_(EL)=567 nm),whereas orange-red phosphorescence for 2(λ_(EL)=624 nm)and deep red emission for 3(λ_(EL)=625 nm)with a peak external quantum efficiency of 16.5%,8.4%and 13.6%,respectively.展开更多
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the financial support from the Postdoctoral Science Foundation of China(2021M702810)the Haihe Laboratory of Sustainable Chemical Transformations(CYZC202103)the National Natural Science Foundation of China(21978200 and 22222808)。
文摘Antioxidants addition is believed as a facile and effective way to improve jet fuel thermal oxidation stability.However,amine antioxidants,as one of the most important antioxidants,have not received sufficient attention in the field of jet fuel autoxidation yet.Herein,the inhibition efficiency and mechanism of decane and exo-tetrahydrodicyclopentadiene(THDCPD)oxidation by di-4-tert-butylphenylamine(diarylamine)was experimentally and theoretically investigated.The results show that diarylamine can significantly inhibit decane oxidation but is less efficient for THDCPD oxidation,which is attributed to the higher energy barrier of retro-carbonyl-ene reaction(rate-determining step)in THDCPD than that in decane during diarylamine regeneration.However,the addition of diarylamine will cause undesirable color change after accelerated oxidation and produce slightly more deposits during high-temperature thermal oxidative stress for both decane and THDCPD.The results provide significant implications for the future design of effective antioxidant additives for high-performance jet fuel.
基金supported by National Key Research and Development Program of China(No.2016YFC0502004-2)Applied Basic Research Program of Sichuan Province(No.2014JY0063)
文摘Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^（13） C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani,Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC_（50） values of 0.013, 1.608 and 1.874 mg/m L, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC_（50） value of 22.21 mg/m L. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.
基金supported by the National Natural Science Foundation of China (31670576)Introduction of the International Advanced Forestry Science and Technology Program (20154-44)
文摘A series of dehydroabietic acid-based diarylamines have been synthesized in order to investigate their fluorescent properties, photostability, cell toxicity and in vitro fluorescence imaging. The geometries as well as their molecular properties were optimized at the B3LYP/6-31G~* level using Gaussian 03. The results indicate that molecular geometry, HOMO and LUMO energies, and energy gaps are important to predict absorption and fluorescent properties. Five of the compounds can be effectively taken up by human cervical carcinoma, human hepatocellular carcinoma SMMC-7721, human gastric cancer SGC-7901 and human lung adenocarcinoma A549 cells and strong blue fluorescent signals are detected in these cells. These compounds are potential candidates for fluorescent probes in biological diagnosis.
基金supported by the National Key Research and Development Program of China(nos.2018YFA0703200 and 2018YFA0209401)the National Natural Science Foundation of China(nos.61890940,52073063,51903052,and 21733003)+1 种基金the Shanghai Pujiang Project(no.19PJ1400700),the Natural Science Foundation of Shanghai(no.21ZR1409600)the Program for Professor of Special Appointment(Eastern Scholar)at the Shanghai Institutions of Higher Learning.
文摘A mild one-step radical-to-radical synthetic strategy has been developed to directly produce a new family of diarylamine-substituted tris(2,4,6-trichlorophenyl)methyl(TTM)radicals TTM-DPA,TTM-DBPA,and TTM-DFA.The obtained TTM radical derivatives are extremely stable during chromatography purification and long-term storage in the solid state.
基金support from the National Natural Science Foundation of China(Grants 92061202 and 21801242)the Fujian Science and Technology Project(Grant 2020L3022)the Strategic Priority Research Program of Chinese Academy of Sciences(Grant XDB20000000).
文摘In this work,4-substituted phenylacetylides with electron-rich N,N’-diarylamine groups are used for the design of triphosphine-supported PtAu_(2) complexes with red phosphorescence.Although PtAu_(2) complex 1 with 4-ethynyl-N,N’-diphenylaniline displays orange emission in CH_(2)Cl_(2) solution,highly efficient red phosphorescence is attained upon using 5-ethynyl-N,N’-diphenylthiophen-2-amine(2)or 2-ethynyl-4-phenyl-4H-dithieno[3,2-b:2’,3’-d]pyrrole(3)in place of 4-ethynyl-N,N-diphenylaniline(1).In contrast to the intense phosphorescence of complexes 1 and 3 in degassed CH_(2)Cl_(2) solution at ambient temperature,complex 2 shows a quite weak phosphorescence as well as fluorescence of the acetylide ligand due to incomplete energy transfer from acetylide ligands to PtAu_(2) centres.Since the phosphorescence efficiency of the doping films is as high as 98.3%,complexes 1–3 are excellent phosphorescent dopants in organic light-emitting diodes(OLEDs).Solution-processed OLEDs showed high-efficiency yellow emission for complex 1(λ_(EL)=567 nm),whereas orange-red phosphorescence for 2(λ_(EL)=624 nm)and deep red emission for 3(λ_(EL)=625 nm)with a peak external quantum efficiency of 16.5%,8.4%and 13.6%,respectively.
