The title compound 2,2-dithiophene-naphthopyran （C21H14OS2, Mr = 346.44） was synthesized and characterized by IR,^1lH NMR, elemental analysis and single-crystal X-ray diffraction. It belongs to the monoclinic system...The title compound 2,2-dithiophene-naphthopyran （C21H14OS2, Mr = 346.44） was synthesized and characterized by IR,^1lH NMR, elemental analysis and single-crystal X-ray diffraction. It belongs to the monoclinic system, space group P21/n, with a = 8.2349（14）, b = 6.1964（11）, c = 32.458（5）A, β= 95.051（3）°, V= 1649.8（5）A^3, Z = 4, Dc = 1.395 g/cm^3,μ = 0.327 cm^-1, F（000） = 720, the final R = 0.0559 and wR = 0.1442 for 3370 observed reflections （I 〉 2σ（I））. X-ray analysis revealed that the interatomic distance of C（13）-O（1） is 1.456（3）A, longer than that of normal C-O bond （1.41 - 1.43 A） in a six-membered heterocycle. The UV-vis spectra of the title compound showed that it exhibits excellent photochromic property in polyester coating and solutions.展开更多
The photochromic properties and reaction mechanism of title compounds have been examined with steady method on compounds 3-phenyl-3-[3-methylbenzothiophene-2-yl]-3H-naphtho[2,1-b]pyran (1) and 3-phenyl-3-[benzofuran-2...The photochromic properties and reaction mechanism of title compounds have been examined with steady method on compounds 3-phenyl-3-[3-methylbenzothiophene-2-yl]-3H-naphtho[2,1-b]pyran (1) and 3-phenyl-3-[benzofuran-2-yl]-3H-naphtho[2,1-b]pyran (2) and nanosecond laser flash photolysis techniques on compound 3-phenyl-3-[1,2-dimethylindol-3-yl]-3H-naphtho[2,1-b]pyran (3). The influence of oxygen on transient spectra and decay kinetics of compound 3 has been investigated. Both excited singlet state and triplet state are involved in the photochromic mechanism of compound 3. The influence of molecular structure on photochromic behavior has been studied also. Decay kinetics indicated that the lifetime of colored forms of 1 and 2 were several orders of magnitude longer than that of 3.展开更多
A series of naphthopyrans with hydrazone unit （8a-8m）, were synthesized and characterized by 1H NMR, 13C NMR, IR and HRMS. The photochromic properties were investigated under continuous irradiation, in particular re...A series of naphthopyrans with hydrazone unit （8a-8m）, were synthesized and characterized by 1H NMR, 13C NMR, IR and HRMS. The photochromic properties were investigated under continuous irradiation, in particular re- gard to the fatigue resistance and the lifetime of the colored open form in solution and polymers. The results showed that these compounds had both good photochromic properties and high fatigue resistance. Detailed studies showed that representative compound 8d （3,3-di-4-methoxybenzoic acid methylenehydrazino-[3H]-naphtho [2,1-b]pyran） had good photochromic properties in THF solution, in solid state, and in polymers, and exhibited a significant ba- thochromic shift in the spectra of the open forms compared to known naphthopyrans 9 （3,3-diphenyl-[3H]- naphtho[2,1-b]pyran）. On the other hand, the higher melting points of target compounds are promising for the polymer film preparation through hot-melt method.展开更多
A series of substituted naphthopyran derivatives are synthesized via the three-component condensation reaction of aromatic aldehydes,malononitrile and naphthol promoted by alkaline ionic liquid(OH).This proposed metho...A series of substituted naphthopyran derivatives are synthesized via the three-component condensation reaction of aromatic aldehydes,malononitrile and naphthol promoted by alkaline ionic liquid(OH).This proposed method is efficient and environmentally friendly.展开更多
In the presence of K2CO3, 2-hydroxyethyltripheny phosphonium bromide (1) reacts with substituted salicylaldehyde (2) and 2-hydroxy-1 naphthaldehyde (4) at 110 ℃ in a sealed tube. The title compounds were prepared in ...In the presence of K2CO3, 2-hydroxyethyltripheny phosphonium bromide (1) reacts with substituted salicylaldehyde (2) and 2-hydroxy-1 naphthaldehyde (4) at 110 ℃ in a sealed tube. The title compounds were prepared in medium yield. The ratio of bromide (1) to aldehyde derivatives was also discussed in this paper.展开更多
The title compound, 2,2-bis（4-tertial butyl phenyl） naphthopyran, has been prepared and characterized by means of IR, ^1H NMR and elemental analysis, and its crystal structure was determined with X-ray diffraction i...The title compound, 2,2-bis（4-tertial butyl phenyl） naphthopyran, has been prepared and characterized by means of IR, ^1H NMR and elemental analysis, and its crystal structure was determined with X-ray diffraction in the ring-opened form after hydrolyzation. It belongs to monoclinic, space group P21/c, with a = 14.358（3）, b = 7.6725（15）, c = 24.470（5） А, β= 97.147（4）°, C_33H_36O2, Mr=464.62, V= 2674.8（9）А^3, Z = 4, Dc = 1.154 g/cm^3,μ= 0.070 mm^-1, F（000） = 1000, the final R = 0.0514 and wR = 0.1272 for 5444 observed reflections （I 〉 2σ（I））. X-ray analysis revealed that the C（13）-O（1） bond of the title compound cracks after UV irradiation, the six-membered heterocycles are destroyed, and zwitterionic intermediates come into being. The molecular structure in the ring-opened form is obtained after hydrolyzation. It is infrequent that the single-crystal structure is determined in a ring-opened form. A two-dimensional framework is formed by O-H…O and CAr-H…O hydrogen bonds. The UV-vis spectra show that the title compound exhibits excellent photochromic properties in solutions and polymers.展开更多
Several new pyrazolo[4,3-b] pyridines 7a, b were prepared by reacting arylidenemalononitriles 1a, c or 1i, j with 4-nitrosoantipyrine 4. Reacting 1a, b, d with 4-azidomethylcarbonylantipyrine 8 give 2-aminopyrrole 14....Several new pyrazolo[4,3-b] pyridines 7a, b were prepared by reacting arylidenemalononitriles 1a, c or 1i, j with 4-nitrosoantipyrine 4. Reacting 1a, b, d with 4-azidomethylcarbonylantipyrine 8 give 2-aminopyrrole 14. Pyrano[3,2-c] quinolines 20a, b and 23 were obtained by reacting 4-hydroxyquinoline 15 with 1g, h, 2b respectively. Reaction of 1 with naphthalenediols 24, 27 and 29 yield naphthodipyrans 26a, b, 28a, b and 30a。展开更多
基金The work was supported by the National Natural Science Foundation of China (Nos 20602020 and 20490210)
文摘The title compound 2,2-dithiophene-naphthopyran （C21H14OS2, Mr = 346.44） was synthesized and characterized by IR,^1lH NMR, elemental analysis and single-crystal X-ray diffraction. It belongs to the monoclinic system, space group P21/n, with a = 8.2349（14）, b = 6.1964（11）, c = 32.458（5）A, β= 95.051（3）°, V= 1649.8（5）A^3, Z = 4, Dc = 1.395 g/cm^3,μ = 0.327 cm^-1, F（000） = 720, the final R = 0.0559 and wR = 0.1442 for 3370 observed reflections （I 〉 2σ（I））. X-ray analysis revealed that the interatomic distance of C（13）-O（1） is 1.456（3）A, longer than that of normal C-O bond （1.41 - 1.43 A） in a six-membered heterocycle. The UV-vis spectra of the title compound showed that it exhibits excellent photochromic property in polyester coating and solutions.
基金Acknowledgements This work was supported by the National Research Fund for Fundamental Key Projects of China (Grant No. G1999033005) and National Natural Science Foundation of China (Grant No. 29832030).
文摘The photochromic properties and reaction mechanism of title compounds have been examined with steady method on compounds 3-phenyl-3-[3-methylbenzothiophene-2-yl]-3H-naphtho[2,1-b]pyran (1) and 3-phenyl-3-[benzofuran-2-yl]-3H-naphtho[2,1-b]pyran (2) and nanosecond laser flash photolysis techniques on compound 3-phenyl-3-[1,2-dimethylindol-3-yl]-3H-naphtho[2,1-b]pyran (3). The influence of oxygen on transient spectra and decay kinetics of compound 3 has been investigated. Both excited singlet state and triplet state are involved in the photochromic mechanism of compound 3. The influence of molecular structure on photochromic behavior has been studied also. Decay kinetics indicated that the lifetime of colored forms of 1 and 2 were several orders of magnitude longer than that of 3.
基金Project supported by the National Natural Science Foundation of China （Nos. 20971071, 20602020）.
文摘A series of naphthopyrans with hydrazone unit （8a-8m）, were synthesized and characterized by 1H NMR, 13C NMR, IR and HRMS. The photochromic properties were investigated under continuous irradiation, in particular re- gard to the fatigue resistance and the lifetime of the colored open form in solution and polymers. The results showed that these compounds had both good photochromic properties and high fatigue resistance. Detailed studies showed that representative compound 8d （3,3-di-4-methoxybenzoic acid methylenehydrazino-[3H]-naphtho [2,1-b]pyran） had good photochromic properties in THF solution, in solid state, and in polymers, and exhibited a significant ba- thochromic shift in the spectra of the open forms compared to known naphthopyrans 9 （3,3-diphenyl-[3H]- naphtho[2,1-b]pyran）. On the other hand, the higher melting points of target compounds are promising for the polymer film preparation through hot-melt method.
文摘A series of substituted naphthopyran derivatives are synthesized via the three-component condensation reaction of aromatic aldehydes,malononitrile and naphthol promoted by alkaline ionic liquid(OH).This proposed method is efficient and environmentally friendly.
文摘In the presence of K2CO3, 2-hydroxyethyltripheny phosphonium bromide (1) reacts with substituted salicylaldehyde (2) and 2-hydroxy-1 naphthaldehyde (4) at 110 ℃ in a sealed tube. The title compounds were prepared in medium yield. The ratio of bromide (1) to aldehyde derivatives was also discussed in this paper.
基金supported by the National Natural Science Foundation of China (Nos. 20602020 and 20490210)
文摘The title compound, 2,2-bis（4-tertial butyl phenyl） naphthopyran, has been prepared and characterized by means of IR, ^1H NMR and elemental analysis, and its crystal structure was determined with X-ray diffraction in the ring-opened form after hydrolyzation. It belongs to monoclinic, space group P21/c, with a = 14.358（3）, b = 7.6725（15）, c = 24.470（5） А, β= 97.147（4）°, C_33H_36O2, Mr=464.62, V= 2674.8（9）А^3, Z = 4, Dc = 1.154 g/cm^3,μ= 0.070 mm^-1, F（000） = 1000, the final R = 0.0514 and wR = 0.1272 for 5444 observed reflections （I 〉 2σ（I））. X-ray analysis revealed that the C（13）-O（1） bond of the title compound cracks after UV irradiation, the six-membered heterocycles are destroyed, and zwitterionic intermediates come into being. The molecular structure in the ring-opened form is obtained after hydrolyzation. It is infrequent that the single-crystal structure is determined in a ring-opened form. A two-dimensional framework is formed by O-H…O and CAr-H…O hydrogen bonds. The UV-vis spectra show that the title compound exhibits excellent photochromic properties in solutions and polymers.
文摘Several new pyrazolo[4,3-b] pyridines 7a, b were prepared by reacting arylidenemalononitriles 1a, c or 1i, j with 4-nitrosoantipyrine 4. Reacting 1a, b, d with 4-azidomethylcarbonylantipyrine 8 give 2-aminopyrrole 14. Pyrano[3,2-c] quinolines 20a, b and 23 were obtained by reacting 4-hydroxyquinoline 15 with 1g, h, 2b respectively. Reaction of 1 with naphthalenediols 24, 27 and 29 yield naphthodipyrans 26a, b, 28a, b and 30a。
