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在超声波辐射条件下,以Fischer碱、1-亚硝基-2,7-二羟基萘为原料,无水乙醇为溶剂快速合成了三个螺嗪类光致变色化合物,通过1 H NMR、IR对目标产物的结构进行了表征,讨论了超声辐射时间对合成产率的影响,利用超声波法合成螺噁嗪类光致变色化合物反应速率快、产率有所提高. 相似文献
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设计合成了一系列含席夫碱基的螺吡喃双功能光致变色材料4a~4n. 通过1H NMR, IR和HRMS对其结构进行了表征. 研究了化合物在几种溶剂和PMMA膜中的光致变色性质, 研究了化合物4a在甲醇中, 以及化合物4a和4f在高分子介质聚甲基丙烯酸甲酯(PMMA)中的消色过程. 结果表明, 化合物4e在PMMA膜中光照后呈现出与其它化合物不同的颜色, 为罕见的绿色. 化合物4a在二氯甲烷溶液中有良好的荧光性能. 所合成的新型含席夫碱基的螺吡喃双功能光致变色材料在甲醇、二氯甲烷和环己烷溶液中及在PMMA膜中均表现出良好的光致变色性质. 相似文献
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具有光致变色和发光性能的有机化合物的合成及其性能研究 总被引:8,自引:0,他引:8
以吲哚啉螺苯并吡喃与香豆素衍生物为原料,用DcC缩合酯化法在温和条件下合成了8种新的具有光致变色和发光性能的化合物,确定了结构,研究了紫外光谱、荧光光谱及光致变色性.所得化合物同时具有光致变色和发荧光的双重特性,而且荧光光谱中有两个激发波长,每一个波长对应产生一个不同的荧光发射峰. 相似文献
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与二茂铁酰基相连的螺噁嗪的合成、结构及性质 总被引:3,自引:1,他引:2
在二环已基碳二亚胺(DCC)存在下, 将9′-羟基螺噁嗪与二茂铁甲酸进行酯化缩合, 合成了一种与二茂铁酰基相连的螺噁嗪衍生物2, 用核磁共振氢谱、碳谱、红外光谱、高分辨质谱和X射线单晶衍射对其结构进行了表征. 化合物2在几种有机溶剂中都表现出了良好的光致变色性质; 通过实验证明了在无冰水浴冷却条件下, 用高压汞灯照射时化合物2在二氯甲烷中表现出的特殊变色性是酸致变色的结果; 同时还研究了化合物2在固体PMMA薄膜中的光致变色性质. 在高压汞灯照射下,化合物2在二氯甲烷溶液中显示了良好的荧光性. 循环伏安法测定结果表明化合物2具有良好的氧化还原可逆性. 相似文献
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微波法快速合成光致变色螺(口恶)嗪 总被引:4,自引:0,他引:4
螺嗪(Spiroxazine)是20世纪70年代在螺吡喃基础上发展起来的一类具有良好光致变色性能的化合物,具有很高的抗疲劳性和光稳定性,具有潜在的商业应用前景[1-4],可用作光信息储存材料和光致变色镜片(PhotochromicLens)。6 哌啶取代的吲哚啉螺萘并嗪[5-11]相对于未取代的母体化合物具有更优异的光致变色性能,但是文献中的合成方法步骤繁琐、反应时间长、产率较低。本文利用微波合成了6 哌啶基(氰基)吲哚啉螺嗪,合成路线如下:1 实验部分1.1 仪器和试剂显微熔点仪(四川大学科仪厂),温度计未经校正;美国P… 相似文献
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吲哚啉螺吡喃是一种重要的光致变色化合物,由于具有良好的变色回复性、抗疲劳性而得到广泛的关注.本文合成了1′-羟乙基-3′,3′-二甲基吲哚啉-6-硝基螺吡喃,研究了该化合物在紫外-可见光交替照射下紫外吸收强度的变化,并测试了光照前后化合物的荧光光谱.在开环态时,化合物具有优良的荧光性能,可以成功应用于细胞成像,在活细胞中可获得清晰的荧光成像图,同时也可以发挥螺吡喃光致变色可循环、耐疲劳等优势. 相似文献
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Zaichenko N. L. Kikot" G. S. Pleshkova A. P. Shiyonok A. I. Kol"tsova L. S. Marevtsev V. S. 《Russian Chemical Bulletin》2001,50(3):470-475
Direct bromination of photochromic compounds of the spironaphthoxazine and spironaphthopyran series was performed using N-bromosuccinimide to obtain both photochromic bromine-substituted spiro compounds and nonphotochromic 2-(naphtho[1,2-d]oxazol-2-yl)-3H-indolium bromides. The structures of the resulting products were established by NMR spectroscopy and mass spectrometry. The mechanism of bromination taking into account the involvement of both closed and open (colored) forms of spiro compounds was proposed. 相似文献
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Yu. S. Alekseenko B. S. Lukyanov A. N. Utenyshev E. L. Mukhanov M. E. Kletskii V. V. Tkachev N. N. Kravchenko V. I. Minkin S. M. Aldoshin 《Chemistry of Heterocyclic Compounds》2006,42(6):803-812
Novel series of photochromic indoline and benzoxazine spiropyrans containing ortho-placed formyl and hydroxyl groups in the
benzene ring of the chromene part of the molecule have been prepared. X-ray analysis has shown that, depending on the structure
of the heterocyclic component in the spiro cyclization reaction different, nonequivalent formyl groups of 2,4-dihydroxyisophthalaldehyde
can participate. The synthesized compounds were used as original analogs of salicylaldehyde. The novel photochromic bispyropyrans
prepared contain two different asymmetric spiro carbon atoms.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 919–929, June, 2006. 相似文献
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A review of the results of studies on photoinduced aggregation of photochromic spiro compounds of the class of spiropyrans and spirooxazines is presented. The possibility to form aggregates of photoinduced species of various types, in particular, H and J aggregates, in liquid and solid polymer solutions as well as in photochromic polymers, amorphous films, and mono-and polymolecular layers is shown. The main fields of applications of nanostructured photochromic systems are considered. 相似文献
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The photochromic spiropyrans and spirooxazine having a succinimidyl ester or isothiocyanate pendant group can form covalent products with transaminated DNA.The absorption spectra and solid reflection spectra of modified DNA with these photochromic spiro compounds were investigated. 相似文献
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Tan Y Hartmann T Huch V Dürr H Valat P Wintgens V Kossanyi J 《The Journal of organic chemistry》2001,66(4):1130-1137
A new photochromic family of tetrahydroazepinoisoquinolines (THAI) 4a-i has been prepared. It undergoes light-induced ring opening from spiro compounds 4 to betaines 3 that decolorize in a very fast cyclizing reaction. Depending on substitution of the precursors 1 and 6, the photochromic styryltetrahydroindolizines (THI) 5k-q are formed in a periselective way. The conformation and configuration of the new photochromic THAI 4 and THI 5 were investigated by NMR and the structure of both compounds was proven by X-ray analysis. The photochromic properties were studied by laser flash photolysis, which afforded the lifetime of the colored form 3 and 3' in the micro- or nanosecond range. 相似文献
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N. A. Voloshin A. V. Chernyshev A. V. Metelitsa E. B. Gaeva V. I. Minkin 《Russian Chemical Bulletin》2011,60(9):1921-1926
Novel photochromic 5??-(1,3-benzothiazol-2-yl)-substituted spiro[indoline-2,3??-naphthopyrans] possessing luminescence properties in both the cyclic and merocyanine forms were synthesized. Unlike the 8??-(1,3-benzothiazol-2-yl)-substituted benzopyran analogs, the synthesized compounds are characterized by the lower relative stability of the merocyanine isomers. 相似文献
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Fluorescence modulation by a class of photochromic perimidine spirodimers, which exhibit a characteristic fluorescence associated with their photochromic reactions, has been described. Upon irradiation using 365 nm light, these non-fluorescent spiro molecules undergo a thermally-reversible ring opening at their spiro junction resulting in the generation of strong fluorescence. The fluorescing species is distinctly different from both the stable ring-closed and the ring-opened compounds, though it appears to have been formed from and remains in equilibrium with the photochemically generated ring-opened form. While the fluorescing species possesses a narrow absorption band with its maximum centered at 500 nm, the ring-opened form exhibits a broad absorption across the visible region with two maxima centered at 410 and 650 nm, respectively. After initiating the photochromic reactions in these molecules using 365 nm light, purely photochemically-controlled fluorescence modulation can be carried out using two wavelengths in the visible region, that is, 500 and 700 nm, while the equilibrium concentration of the ring-opened form and the fluorescing species is controlled. Fluorescence modulation is attained also by controlling the ratio of the ring-closed and ring-opened forms by photochemical ring-opening and thermal ring-closing reactions. The study on the effect of substitution of these molecules suggests that by extending the conjugation of the perimidine core in the ring-opened form the molecule is rendered non-fluorescent and hence it can be assumed that the perimidine core forms the fluorescing entity of the molecule. 相似文献
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N. A. Voloshin A. V. Chernyshev S. O. Bezuglyi A. V. Metelitsa E. N. Voloshina V. I. Minkin 《Russian Chemical Bulletin》2008,57(1):151-158
The Duff formylation of 5-bromo- or 5-chloro-8-hydroxyquinoline leads to the corresponding 7-formyl derivatives, condensation of which with 2-methyleneindolines or 3H-indolium halides in the presence of a base afforded new photochromic 6′-halo-substituted spiro[indoline-2,2′-2H- pyrano[3,2-h]quinolines]. Thermal and photo-induced isomerization of compounds obtained have been investigated by 1H NMR and UV spectroscopy. 相似文献
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Hiroyuki Nakazumi Koichiro Makita Rie Nagashiro 《Journal of Sol-Gel Science and Technology》1997,8(1-3):901-909
New photochromic thin gel films have been prepared by the dipping method from a sol-gel coating solution containing Malachite
Green Leucocyanide soluble in sol and super-fine dispersed solution of spiropyran or spironaphthooxazine, which was effective
to increase the concentration of photochromic compounds in gel film. Photochromism of these gel films is compared with that
in sol under the conditions of acid catalysis. Though in sols using spiropyran and Malachite Green Leucocyanide normal photochromism
was not observed, photochromism in thin gel films prepared from the same sol was confirmed. Normal photochromism of spironaphthooxazine
in thin gel films was similar to that in solution. The reaction rate from the colored form to the spiro form of spiropyran
and spironaphthooxazine in thin gel film is dependent on the gel matrix, which is influenced by the reaction time of the sol. 相似文献
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Jian Lin Wenxiang Chai Li Song Laishun Qin Kangying Shu 《Acta Crystallographica. Section C, Structural Chemistry》2009,65(12):o621-o623
In the course of our synthesis of hybrid photochromic compounds, the unexpected new organic photochromic title compound, C29H33N3O2, (I), was obtained. It is a derivative of the parent spirooxazine 1,3,3‐trimethyl‐6′‐(piperidin‐1‐yl)spiro[indoline‐2,3′‐3′H‐naphtho[2,1‐b][1,4]oxazine], (II). The 2′‐ethoxy group gives (I) different photochromic properties from its parent spirooxazine (II). 相似文献