The selective bromination of paeonol (4-methoxy-2-hydroxyacetophenone) has been studied as function of solvents(methanol, ethanol, chloroform-ethyl acetate), reaction time, temperature and the mole ratio of reagents. ...The selective bromination of paeonol (4-methoxy-2-hydroxyacetophenone) has been studied as function of solvents(methanol, ethanol, chloroform-ethyl acetate), reaction time, temperature and the mole ratio of reagents. The higher yield was obtained in polar solvents than in non-polar ones. The best solvent appeared methanol, and the mixtures of polar solvents were better than any single of them, except methanol. Paeonol and cupric bromide in mole ratio of 1∶2 in methanol under reflux temperature for five hours gave a bromination product in yield of 63.3%.展开更多
We report a facile synthesis of a [1,12-b,c,d]-cyclopenta-fused perylene 5 from the parent perylene via a formylation-oxidative esterification–nucleophilic additionfollowed-by-Friedel–Crafts alkylation strategy. Com...We report a facile synthesis of a [1,12-b,c,d]-cyclopenta-fused perylene 5 from the parent perylene via a formylation-oxidative esterification–nucleophilic additionfollowed-by-Friedel–Crafts alkylation strategy. Compared with the perylene, dye 5 exhibits much higher solubility,smaller energy gap, and can undergo regio-selective bromination at the peri-positions. Compared with the Nannulated perylene 8, compound 5 shows lower HOMO energy level and is more stable in air. Therefore, 5 can be regarded a new versatile building block for the development of high-order soluble and stable rylenes and various perylene-based functional materials.展开更多
文摘The selective bromination of paeonol (4-methoxy-2-hydroxyacetophenone) has been studied as function of solvents(methanol, ethanol, chloroform-ethyl acetate), reaction time, temperature and the mole ratio of reagents. The higher yield was obtained in polar solvents than in non-polar ones. The best solvent appeared methanol, and the mixtures of polar solvents were better than any single of them, except methanol. Paeonol and cupric bromide in mole ratio of 1∶2 in methanol under reflux temperature for five hours gave a bromination product in yield of 63.3%.
基金Project supported by the Key Scientific and Technological Project of Henan Province(No.192102310031)the Scientific Research Project of Henan Province(No.19B150018)the Nanhu Scholars Program for Young Scholars of Xinyang Normal University and the Young Core Instructor Program of Xinyang Normal University(No.2018GGJS-05)~~
基金supported by MOE Tier 2 Grant(MOE2011-T2-2-130)A*STAR-DST joint Grant(IMRE/14-2C0239)A*STAR JCO Grant(1431AFG100)
文摘We report a facile synthesis of a [1,12-b,c,d]-cyclopenta-fused perylene 5 from the parent perylene via a formylation-oxidative esterification–nucleophilic additionfollowed-by-Friedel–Crafts alkylation strategy. Compared with the perylene, dye 5 exhibits much higher solubility,smaller energy gap, and can undergo regio-selective bromination at the peri-positions. Compared with the Nannulated perylene 8, compound 5 shows lower HOMO energy level and is more stable in air. Therefore, 5 can be regarded a new versatile building block for the development of high-order soluble and stable rylenes and various perylene-based functional materials.
