Citation: Jiang Xin-Dong, Shao Zhumei, Sun Changliang, Yue Shuai, Shang Rong, Yamamoto Yohsuke. Development of aryl-containing dipyrrolyldiketone difluoroboron complexes (BONEPYs): Tune the hydrogen bond o-C-H ··· F for fluoride recognition[J]. Chinese Chemical Letters, ;2020, 31(5): 1317-1321. doi: 10.1016/j.cclet.2019.09.053 shu

Development of aryl-containing dipyrrolyldiketone difluoroboron complexes (BONEPYs): Tune the hydrogen bond o-C-H ··· F for fluoride recognition

a.
College of Applied Chemistry, Shenyang University of Chemical Technology, Shenyang 110142, China
b.
Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526, Japan

xdjiang@syuct.edu.cn

Received Date: 18 September 2019
Revised Date: 26 September 2019
Accepted Date: 29 September 2019
Available Online: 1 October 2019

Figures(11)

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 BONEPYendo-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 complex 4·(5)F^-. The energy differences between the different conformations were calculated using DFT methods, which is consistent to the experimental observations.
- BONEPY,
- Hydrogen bond,
- Fluorescent dye,
- Fluoride anion,
- Probe
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1.
沈阳化工大学材料科学与工程学院沈阳 110142