42103-98-0Relevant academic research and scientific papers
A novel photochromic fulgide based on porphyrin for nondestructive information processing
Yu, Chuan-Ming,Hu, Bing-Cheng,Gong, Zhi-Hui,Liu, Cheng,Li, Ji-Ting
, p. 1767 - 1770 (2016)
A fulgide connected to porphyrin (FUL-TPP) can transform its open isomer to closed isomer upon the irradiation with UV or visible light. Herein, they can be used to write binary data. Furthermore, the open form can emit luminescence but the closed cannot form while irradiated in another light that will not cause the optical chemical reaction. Therefore, the data can be read out without destruction.
Photochromism of rotation-hindered furylfulgides influenced by steric modifications
Struebe, Frank,Siewertsen, Ron,Soennichsen, Frank D.,Renth, Falk,Temps, Friedrich,Mattay, Jochen
experimental part, p. 1947 - 1955 (2011/04/27)
The syntheses of a bicyclic furylfulgide 14 and a (benzofuryl)fulgide 15 with increased steric constraints are described. Their photochromic behaviors were analyzed by means of UV/Vis spectroscopic measurements, X-ray crystallography, and NMR experiments, and the results were compared to those of the furyl(methyl)fulgide 12 and the furyl(isopropyl)fulgide 13. Compounds 13E and 14E exhibit large quantum yields of 0.57 and 0.53 for the coloration reaction (E) → (C) compared with 12E and 15E (0.23 and 0.17). After irradiation with 350 nm light, 13E and 14E are transformed into the closed (C) forms almost quantitatively, whereas 12E and 15E result in a photostationary state with mixtures of the (E), (Z), and (C) forms. The crystal structures obtained for 13E, 14E, and 15E show that the fulgides adopt cyclizable helical (P)-Eα conformations with no significant differences in atomic distances in the hexatriene unit. 2D- and temperature-dependent NMR experiments showed that the enantio- and diastereotopomerization processes were suppressed in a fulgide for the first time. Compound 14E populates only the E α conformational state. In contrast, 13E and 15E both exist in the cyclizable Eα and the non-cyclizable Eβ conformations in solution. Due to the annulated benzene ring, 15E exhibits a higher thermodynamic barrier than 13E, so the "belly roll" process was reduced for 15, but the (E) → (Z) isomerization could not be suppressed. The structural modification of 14 successfully suppressed the (E) → (Z) isomerization as well as the belly roll process. The way in which the isomerization reaction is suppressed by steric hindrance could not be fully elucidated by using these methods. Copyright
Synthesis of hybrid photochromes containing fulgimide and salicylidenaniline fragments and study of their properties
Luyksaar,Platonova,Krayushkin,Barachevskii,Molchanov
body text, p. 861 - 866 (2012/02/05)
Fulgimide salicylidenaniline derivatives were synthesized and studied in solutions and solid-phase films. It was found that the compounds obtained exhibit photochromic properties in different aggregate states. Comparative studies showed that the nature of substituents in the aldehyde moiety of the fulgimide azomethine fragments has little effect on the photochromic properties of the compounds obtained.
Synthesis of photochromic bisfulgimides by the condensation of (3Z)-3-[1-(2,5-dimethyl-3-thienyl)-ethylidene]-4-isopropylidene-2,5-furandione with aromatic diamines
Luyksaar,Krayushkin,Pyankov,Barachevsky
experimental part, p. 822 - 828 (2011/07/29)
The first representatives of thiophene derivatives with two fulgimide fragments in one molecule have been obtained by the condensation of (3Z)-3-[1-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidene-2,5-furandione with aromatic diamines. The photochromic properties of the obtained compounds have been investigated and the effect of a spacer, linking the two fulgimide fragments, on the reaction rates of photocoloration and photodecoloration of these compounds has been studied.
Bromine-induced facile synthesis of butenolides and spirobutenolides from sterically congested tetrasubstituted dialkyl alkylidene succinates
Patel, Ramesh M.,Argade, Narshinha P.
experimental part, p. 1188 - 1194 (2010/05/19)
Starting from sterically congested tetrasubstituted dialkyl alkylidene succinates, facile general approach to several dialkyl substituted butenolides and spirobutenolides with the generation of quaternary carbon center has been demonstrated via bromine-in
Microwave-assisted synthesis of photochromic fulgides
Nithyanandan, Sivasankaran,Saravanan, Chinnusamy,Senthil, Sengodan,Kannan, Palaninathan
scheme or table, p. 183 - 188 (2010/11/04)
The oxazole and indole based heterocyclic photochromic fulgides were synthesized from their corresponding fulgenic acid derivatives by clay catalysed microwave irradiation methodology. Improved yields of fulgides were observed by the microwave irradiation method as compared other chemical methods employed so far. The proportions of clay (montmorillonite KSF) and isopropenyl acetate play a key role in increasing the yields of fulgides. Indian Academy of Sciences.
Fluorine-substituted azobenzene destabilizes polar form of optically switchable fulgimide unit in copolymer system
Chinnusamy, Saravanan,Palaninathan, Kannan
scheme or table, p. 1565 - 1578 (2011/02/26)
Fulgimide and various size and electronic nature of substituents on the terminal position of azobenzene in the pendant homo/copolymethacrylates were synthesized. Differential scanning calorimetry analysis indicates the homopolymer possessing C-form fulgimide unit exhibited higher Tm than that of E-form of the homopolymer and revealed C-form is highly ordered. Thermal stability suggests azobenzene homopolymers with electron donating substituents have high thermal stability than electron withdrawing substituents. Polarized optical microscopy observation disclosed homopolymers viz., NI, CY, FL, ME, and T-ME exhibited liquid crystalline mesophases between their Tm and Ti. Optical properties of homo/copolymers were investigated by UV-vis and fluorescence spectroscopy. UV-vis spectroscopy displayed C-form fulgimide absorption in F-co-FL around 482 nm which is around 40 nm lesser than C-form of substituted azobenzene copolymers. Similarly, fluorescence pattern of F-co-FL by UV irradiation exhibited emission intensity slowly increased to certain level then decreases with two new emissions at 430 and 480 nm attributed to terminal position of fluorine atom on azobenzene destabilizes polar form (C-form) fulgimide unit in the copolymer.
Synthesis and photochromism of functionalized benzothiophene-based fulgides and fulgimides
Luyksaar,Migulin,Nabatov,Krayushkin
body text, p. 446 - 451 (2011/02/17)
Earlier unknown fulgides and the corresponding functionalized fulgimides containing a primary amino group were obtained. Their photochromism was examined using spectroscopic methods.
Unexpected novel rearrangement reaction: Synthesis of benzo-medium-ring anhydride
Dong, Wen-Liang,Zhao, Bao-Xiang,Wei, Fang,Zuo, Hua,Shin, Dong-Soo
, p. 1224 - 1235 (2008/09/18)
When we attempted to synthesize (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)- 4-(propan-2-ylidene)-dihydrofuran-2,5-dione, we found a novel rearrangement and obtained the unexpected compound that is assigned as benzo-medium-ring anhydride instead of the expected compound. We described the novel rearrangement and a potential method for the synthesis of benzo-medium-ring anhydride derivatives. Copyright Taylor & Francis Group, LLC.
Synthesis and photochromic properties of cycloalkylidene fulgides
Lee, Wei-Woon Wayne,Gan, Leong-Ming,Loh, Teck-Peng
, p. 2473 - 2477 (2007/10/03)
A series of cycloalkylidene fulgides have been synthesized using β,γ-unsaturated diesters, instead of the usual α,β- unsaturated diesters. A study of their photochromic properties revealed that an increase in the cycloalkylidene ring size caused a subsequ
