| Development of aryl-containing dipyrrolyldiketone difluoroboron complexes(BONEPYs):Tune the hydrogen bond o-C—H…F for fluoride recognition |
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| 作者姓名： | Xin-Dong Jiang Zhumei Shao Changliang Sun Shuai Yue Rong Shang Yohsuke Yamamoto |
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| 作者单位： | College of Applied Chemistry;Department of Chemistry |
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| 基金项目： | supported by the National Natural Science Foundation of China(No.21542004);Young and middle-aged scientific and technological innovation talents of Shenyang Science and Technology Bureau(No.RC170140);Liaoning Province Natural Science Foundation(No.20170540721);Basic research on the application of Industrial Development of Shenyang Science and Technology Bureau(No.18013027);Liaoning BaiQianWan Talents Program,and the Distinguished Professor Project of Liaoning province(No.20183532);the Chinese Scholarship Council(No.20183058)for financial support。 |
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| 摘 要： | Dipyrrolyldiketone difluoroboron complexes(BONEPYs)were synthesized by condensation of the corresponding pyrroles and malonyl chloride followed by treatment with BF3·OEt2.The aryl-substituted pyrrole is introduced to form a cyclic system in order to investigate anion binding studies.In BONEPYs 1-3 the o-H of the aryl group forms hydrogen bonding with F to give a more table complex.In contrast,the intramolecular hydrogen-bonded BONEPY endo-4 is more stable than its exo isomer.While adding F,the hydrogen bonds must be broken first to give 4·(3)F.Owing to the electron-rich group(-OMe),the o-H of the phenyl group can hardly interact with F via hydrogen bonding to give the less stable complex4-(5)F.The energy diffe rences between the different conformations were calculated using DFT methods,which is consistent to the experimental observations.
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| 关 键 词： | BONEPY Hydrogen bond Fluorescent dye Fluoride anion PROBE |
| 收稿时间： | 2019-09-18 |
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