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

作     者：Xin-Dong Jiang Zhumei Shao Changliang Sun Shuai Yue Rong Shang Yohsuke Yamamoto Xin-Dong Jiang;Zhumei Shao;Changliang Sun;Shuai Yue;Rong Shang;Yohsuke Yamamoto

作者机构：College of Applied ChemistryShenyang University of Chemical TechnologyShenyang 110142China Department of ChemistryGraduate School of ScienceHiroshima UniversityHigashi-Hiroshima 739-8526Japan 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2020年第31卷第5期

页      面：1317-1321页

核心收录：

学科分类：1001[医学-基础医学(可授医学、理学学位)] 0703[理学-化学] 10[医学] 

基　　金：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 

主　　题：BONEPY Hydrogen bond Fluorescent dye Fluoride anion Probe 

摘      要：Dipyrrolyldiketone difluoroboron complexes(BONEPYs)were synthesized by condensation of the corresponding pyrroles and malonyl chloride followed by treatment with BF3·*** aryl-substituted pyrrole is introduced to form a cyclic system in order to investigate anion binding *** BONEPYs 1-3 the o-H of the aryl group forms hydrogen bonding with F to give a more table *** contrast,the intramolecular hydrogen-bonded BONEPY endo-4 is more stable than its exo *** adding F,the hydrogen bonds must be broken first to give 4·(3)*** 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)*** energy diffe rences between the different conformations were calculated using DFT methods,which is consistent to the experimental observations.