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1.
Photochromic indene derivatives, 1-(2-methyl-1-inden-3-yl)-2-(2-methyl-1-benzothien-3-yl)perfluorocyclopentene and 1-(2-methyl-1-inden-3-yl)-2-(2-methyl-1-benzofuran-3-yl)perfluorocyclopentene, were synthesized and their photochromic performance was examined. 相似文献
2.
Tadatsugu Yamaguchi Manabu HosakaToru Ozeki Masakazu MorimotoMasahiro Irie 《Tetrahedron letters》2011,52(43):5601-5604
Photochromic benzo[b]silole derivatives, 1-(1,1-dimethyl-2-phenylbenzo[b]silol-3-yl)-2-(2-phenylbenzo[b]thien-3-yl)perfluorocyclopentene and 1-(1,1-dimethyl-2-phenylbenzo[b]silol-3-yl)-2-(2-phenyl-1-benzofuran-3-yl)perfluorocyclopentene, were synthesized and their photochromic performance was examined in solution. 相似文献
3.
[structure: see text] An optically active photochromic diarylethene, (S)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-methyl-5-(4-(3-methyl-1-penten-1-yl)phenyl)-3-thienyl]perfluorocyclopentene ((S)-1a), was synthesized. (S)-1a formed two crystalline phases, alpha- and beta-phases. The diarylethene underwent a photochromic reaction in solution and even in the single-crystalline phase. In solution, no diastereoselection was observed. On the other hand, in the beta-crystalline phase, only one diastereomer (S,R,R)-1b was produced. No such diastereoselection was observed in the alpha-crystalline phase. 相似文献
4.
Yang T Pu S Fan C Liu G 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2008,70(5):1065-1072
A new unsymmetrical photochromic diarylethene, 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-methyl-5-(3-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene (1a), was synthesized and its structure was determined by single-crystal X-ray diffraction analysis. Its optical and electrochemical properties, including photochromic reactivity both in solution and in the solid state (PMMA film and the single-crystalline phase), fluorescence and electrochemical properties were investigated in detail. The compound showed excellent photochromism even in the single-crystalline phase by photo-irradiation. In acetonitrile, the open-ring isomer of diarylethene 1 exhibited relatively strong fluorescence at 470nm when excited at 300nm, and its emission intensity decreased along with the photochromism upon irradiation with 313nm light. Its closed-ring isomer showed almost no fluorescence. The electrochemical properties of diarylethene were investigated by performing cyclic voltammetry experiment and its HOMO and LUMO energy level were calculated. 相似文献
5.
Jeong YC Park DG Kim E Ahn KH Yang SI 《Chemical communications (Cambridge, England)》2006,(17):1881-1883
High fatigue-resistant photochromic dithienylethenes were synthesized by controlling the oxidation state of 1,2-bis(2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene (BTF6) and 1,2-bis(2,5-dimethylthien-3-yl)perfluorocyclopentene (DMTF6). 相似文献
6.
Photochromism of metal complexes composed of diarylethene ligands and Zn(II), Mn(II), and Cu(II) hexafluoroacetylacetonates 总被引:1,自引:0,他引:1
Metal complexes composed of bidentate 1,2-bis(2-methyl-5-(4-pyridyl)-3-thienyl)perfluorocyclopentene (1a) and monodentate 1-(2-methyl-5-phenyl-3-thienyl)-2-(2-methyl-5-(4-pyridyl)-3-thienyl)perfluorocyclopentene (2a) photochromic ligands and M(hfac)(2) (M = Zn(II), Mn(II), and Cu(II)) were prepared, and their photoinduced coordination structural changes were studied. X-ray crystallographic analyses showed the formation of coordination polymers and discrete 1:2 complexes for bidentate and monodentate ligands, respectively. The complexes underwent reversible photochromic reactions by alternate irradiation with UV and visible lights in solution as well as in the single-crystalline phase. Upon photoirradiation with UV and visible light, the ESR spectra of the copper complexes of 1a reversibly changed. While the open-ring isomer gave an axial-type spectrum, the photogenerated closed-ring isomer showed a rhombic-type spectrum. This indicates that the photoisomerization induced the change in the coordination structure. 相似文献
7.
Shouzhi Pu Jingkun Xu Liang Shen Qiang Xiao Tianshe Yang Gang Liu 《Tetrahedron letters》2005,46(5):871-875
The photochromic diarylethene, 1,2-bis(2-methyl-5-(2-(1,3-dithiolpentane))-thien-3-yl)perfluorocyclopentene (BMDTP), has been synthesized in high yield and its structure was determined by X-ray crystallographic analysis. The compound undergoes a photochromic reaction both in solution and in the single crystalline phase. In addition, its fluorescence property in solution is discussed. 相似文献
8.
9.
Shou-Zhi PuFu-Shi Zhang Fan SunRu-Ji Wang Xin-Hong ZhouShek-Kiu Chan 《Tetrahedron letters》2003,44(5):1011-1014
The photochromic diarylethene, 1,2-bis(2-methyl-5-(2,2′-dicyanovinyl)-thien-3-yl)perfluorocyclopentene (1a), was synthesized by a novel method. Two kinds of single crystals of the compound were obtained depending on the different recrystallization conditions and their structures were determined by X-ray crystallographic analysis. Allomorphism of the photochromic diarylethene was discovered. The compound underwent a photochromic reaction both in solution and in the single crystalline phase of the anti-parallel conformer. 相似文献
10.
The photochromic diarylethene, 1,2-bis[2-methyl-5-(3-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene (BMTTP), was synthesized and its photochromic kinetics, fluorescence and X-ray structure were investigated. This compound underwent a photochromic reaction both in solution and the single crystalline phase. Its cyclization/cycloreversion process was determined to be zeroth/first order reaction, respectively, and this is the first report on the cyclization/cycloreversion reaction order. In addition, its fluorescence property was also discussed. 相似文献
11.
《Supramolecular Science》1996,3(1-3):87-89
1,2-Diarylethenes with heterocyclic aryl groups, such as benzothiophene rings, underwent thermally irreversible and fatigue resistant photochromic reactions. The photocyclization response time of a dithienylethane was measured to be 1 ps. Gated photochromic reactivity was given to a 1,2-bis(benzothiophen-3-yl) perfluorocyclopentene by introducing intramolecular hydrogen-bond forming groups. 相似文献
12.
Tadatsugu Yamaguchi Tsuyoshi Nakagawa Toru Ozeki Mitsuhiro Fukuda Masakazu Morimoto Shizuka Takami 《Tetrahedron letters》2017,58(47):4447-4449
1,2-Bis(2-methyl-1-benzofuran-3-yl)perfluorocyclopentene shows photochromism in n-hexane at room temperature. We have identified a new compound produced by the thermal decomposition in a mixture of cis- and trans-decahydronaphthalene above 100?°C in the absence of light. 相似文献
13.
Murakami M Miyasaka H Okada T Kobatake S Irie M 《Journal of the American Chemical Society》2004,126(45):14764-14772
The cycloreversion (ring-opening) process of one of the photochromic diarylethene derivatives, bis(2-methyl-5-phenylthiophen-3-yl)perfluorocyclopentene, was investigated by means of picosecond and femtosecond laser photolysis methods. The drastic enhancement of the reaction yield was observed only by the picosecond laser exposure. The excitation intensity effect of the reaction profiles revealed that the successive multiphoton absorption process leading to higher excited states opened the efficient cycloreversion process with a reaction yield of (50 +/- 10)%, while the one-photon absorption directly pumped to a higher excited state did not lead to the efficient cycloreversion reaction. These results indicate that not the energy of the excitation but the character of the electronic state takes an important role in the enhancement of the cycloreversion reaction. 相似文献
14.
Diarylethene derivatives having imino nitroxide and nitronyl nitroxide have been prepared to examine the effect of the radical substituents on the photochromic reactivity of 1,2-bis(2-methyl-1-benzothiophen-3-yl)perfluorocyclopentene. These radical substituents reduce the quantum yields of both cyclization and cycloreversion reactions. The nitronyl nitroxyl moiety is more effective to suppress the reactivity in comparison with the imino nitroxide moiety. [reaction: see text] 相似文献
15.
Novel photochromic single crystals composed of three different kinds of diarylethenes, 1,2-bis(3,5-dimethyl-2-thienyl)perfluorocyclopentene (1a), 1,2-bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene (2a), and 1,2-bis(2-methyl-5-p-methoxyphenyl-3-thienyl)perfluorocyclopentene (3a), have been prepared. The three-component crystals turned yellow, orange, red, purple, blue, green, or black upon irradiation with light of appropriate wavelengths. The colors of the crystals were thermally stable in the dark and completely bleached by irradiation with visible light. Such multicolored photochromic crystals have potential for the application to optoelectronic devices, such as multifrequency three-dimensional optical memory media or full-color displays. 相似文献
16.
Metal complexes composed of ZnCl(2) and bidentate 1,2-bis(2-methyl-5-(4-pyridyl)-3-thienyl)perfluorocyclopentene (1a) and monodentate 1-(2-methyl-5-phenyl-3-thienyl)-2-(2-methyl-5-(4-pyridyl)-3-thienyl)perfluorocyclopentene (2a) photochromic ligands were prepared. X-ray crystallographic analyses showed the formation of a coordination polymer and a discrete 2:1 complex for 1a.ZnCl(2) and 2a(2).ZnCl(2), respectively. While the 2a(2).ZnCl(2) crystal underwent photochromic reaction in the crystalline state by alternate irradiation with UV and visible light, the 1a.ZnCl(2) crystal did not show any photoreactivity. The difference in the photochromic behavior was explained by the difference in the conformation of the diarylethenes in the crystals. 相似文献
17.
Efficient and reversible fluorescence modulation with excellent photo-stability was achieved from a sulfone form of diacetyl diarylethene, 1,2-bis(6-acetyl-2-methyl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentene (DABTFO4). The DABTFO4 emits strong fluorescence in the closed-ring isomer even in the absence of extra fluorophores. The fluorescence quantum yield, fatigue resistance, and photo-cyclization yield of DABTFO4 were significantly improved compared with the unsubstituted 1,2-bis(2-methyl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentene (BTFO4) and the sulfide analogue, 1,2-bis(6-acetyl-2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene (DABTF6). 相似文献
18.
L. G. Vorontsova M. M. Krayushkin Z. A. Starikova M. A. Kalik F. M. Stoyanovich O. Yu. Zolotarskaya D. L. Dzhavadov 《Russian Chemical Bulletin》1990,49(1):77-80
The structures of two hetarylethene photochromes,viz., 1,2-bis(2-ethyl-5-ethylsulfonylthien-3-yl)perfluorocyclopentene and 1,2-bis[5-(benzoxazol-2-yl)-2-methylthien-3-yl]perfluorocyclopentene,
were established by X-ray diffraction analysis. The conformational parameters of the title compounds are considered. The cyclopentene
ring in the former compound is planar and this ring in the latter compound adopts an envelope conformation. There are no overall
conjugated systems in the molecules under study. In both structures, the dihetaryl fragments are rotated with respect to the
perfluorocyclopentene fragments by ∼55°. The thiophene and benzoxazole rings in 1,2-bis[5-(benzoxazol-2-yl)-2-methylthien-3-yl]perfluorocyclopentene
are coplanar.
For Part 3, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 74–77, January, 2000. 相似文献
19.
Shouzhi Pu Tianshe Yang Jingkun Xu Liang Shen Guizhen Li Qiang Xiao Bing Chen 《Tetrahedron》2005,61(27):6623-6629
Four photochromic dithienylethene compounds, 1,2-bis(2-methyl-5-naphthalene-3-thienyl)perfluorocyclopentene 1a, 1,2-bis[2-methyl-5(p-fluorophenyl)-3-thienyl]perfluorocyclopentene 2a, 1,2-bis[2-methyl-5(p-ethoxyphenyl)-3-thienyl]perfluorocyclopentene 3a, and 1,2-bis[2-methyl-5(p-N,N-dimethylaminophenyl)-3-thienyl]perfluorocyclopentene 4a were synthesized, and their optoelectronic properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous films, fluorescences and electrochemical properties were investigated in detail. These dithienylethenes have shown good photochromic behavior both in solution and in PMMA amorphous film. All of them exhibited relatively strong fluorescence and gave a bathochromic shift upon increasing concentration in THF. The irreversible anodic oxidation of 1a, 2a and 4a was observed by performing cyclic voltammetry experiments. 相似文献
20.
L. G. Vorontsova M. M. Krayushkin Z. A. Starikova M. A. Kalik F. M. Stoyanovich O. Yu. Zolotarskaya D. L. Dzhavadov 《Russian Chemical Bulletin》2000,49(1):77-80
The structures of two hetarylethene photochromes,viz., 1,2-bis(2-ethyl-5-ethylsulfonylthien-3-yl)perfluorocyclopentene and 1,2-bis[5-(benzoxazol-2-yl)-2-methylthien-3-yl]perfluorocyclopentene,
were established by X-ray diffraction analysis. The conformational parameters of the title compounds are considered. The cyclopentene
ring in the former compound is planar and this ring in the latter compound adopts an envelope conformation. There are no overall
conjugated systems in the molecules under study. In both structures, the dihetaryl fragments are rotated with respect to the
perfluorocyclopentene fragments by ∼55°. The thiophene and benzoxazole rings in 1,2-bis[5-(benzoxazol-2-yl)-2-methylthien-3-yl]perfluorocyclopentene
are coplanar.
For Part 3, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 74–77, January, 2000. 相似文献