59726-65-7Relevant academic research and scientific papers
Wavelength-Gated Photochemical Synthesis of Phenalene Diimides
Feist, Florian,Walden, Sarah L.,Alves, Jessica,Kunz, Susanna V.,Micallef, Aaron S.,Brock, Aidan J.,McMurtrie, John C.,Weil, Tanja,Blinco, James P.,Barner-Kowollik, Christopher
, p. 10402 - 10408 (2021)
Herein, we pioneer a wavelength-gated synthesis route to phenalene diimides. Consecutive Diels–Alder reactions of methylisophthalaldehydes and maleimides afford hexahydro-phenalene-1,6-diol diimides via 5-formyl-hexahydro-benzo[f]isoindoles as the intermediate. Both photoreactions are efficient (82–99 % yield) and exhibit excellent diastereoselectivity (62–98 % d.r.). The wavelength-gated nature of the stepwise reaction enables the modular construction of phenalene diimide scaffolds by choice of substrate and wavelength. Importantly, this synthetic methodology opens a facile avenue to a new class of persistent phenalenyl diimide neutral radicals, constituting a versatile route to spin-active molecules.
N-(2,3,4,5,6-pentafluorophenyl)maleimide as a powerful dienophile in dearomatizing diels-alder reactions
Hagiwara, Koichi,Iwatsu, Masafumi,Urabe, Daisuke,Inoue, Masayuki
, p. 659 - 672 (2015)
Here we demonstrate that N-(2,3,4,5,6-pentafluorophenyl)maleimide effectively promotes dearomatizing Diels-Alder reactions of 2,5-dimethylbenzene-1,4-diol and naphthalen-2-ol derivatives. The present reactions successfully converted the sp2-rich components to the desired products with multiple sp3-carbons in a single step. The adduct was further derivatized into the intermediate for our synthesis of 9-demethyl-10,15-dideoxyryanodol, an analogue of a sp3-rich natural product, in two steps.
A novel copolymer of methyl methacrylate with N-pentafluorophenyl maleimide: High glass transition temperature and highly transparent polymer
Lou, Liping,Koike, Yasuhiro,Okamoto, Yoshiyuki
, p. 3560 - 3564 (2011)
N-pentafluorophenyl maleimide (PFPMI) was synthesized. The homo and copolymers of PFPMI with methyl methacrylate (MMA) were prepared. The monomer reactivity ratio, r1 (PFPMI) and r2 (MMA) were 0.389 and 1.06 respectively. Q and e values for PFPMI were calculated as 1.00 and 1.30. The refractive indexes of poly(PFPMI) and PMMA were found to be similar; 1.4989 and 1.4953 at 532 nm, respectively. The copolymers exhibited no light scattering, and the film was very transparent. The glass transition temperatures of the PFPMI-co-MMA were in the range of 140 °C-180 °C with the PFPMI content from 18.8 to 65 mol% and the copolymers obtained have high thermal stability (~370 °C). The water absorption of PFPMI-co-MMA was greatly reduced as compared with that of pure PMMA.
Compound containing five-membered nitrogen heterocycle and organic electroluminescent device produced by using compound
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Paragraph 0052-0054, (2018/08/28)
The invention provides a compound containing five-membered nitrogen heterocycle and an organic electroluminescent device produced by using the compound and relates to the technical field of organic photoelectric materials. The compound is simple in preparation method and available in raw materials, has the advantages such as good film forming property and good thermal stability, is beneficial to hole transportation and is capable of remarkably increasing the light emitting efficiency of a device, reducing a driving voltage and prolonging the service life of the device when being applied to anOLED.
Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives
Chen, Hao,Yao, Erdong,Xu, Chi,Meng, Xiao,Ma, Yuguo
supporting information, p. 5102 - 5107 (2014/07/08)
Unusual regio- and stereo-selectivity in Diels-Alder (D-A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio- and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon-carbon coupling reactions.
Synthesis and characterization of fluorinated poly(phenylmaleimide-co- pentafluorophenylmaleimide) for optical waveguides
Choi, Jongwan,Oh, Jin-Woo,Kim, Nakjoong
, p. 1077 - 1080 (2013/07/28)
Fluorinated polymaleimides with high thermal stability and low optical absorption loss in the optical communication wavelength of 1.55 μm were investigated for application in low-loss waveguide materials. The fluorinated polymaleimides were prepared from
Acene-based organic semiconductor materials and methods of preparing and using the same
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Page/Page column 12, (2008/12/07)
Acene-based compounds that can be used to prepare n-type semiconductor materials are provided with processes for preparing the same. Composites and electronic devices including n-type semiconductor materials prepared from these compounds also are provided
