59726-65-7Relevant articles and documents
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.
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.
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.
