The investigation of proton transfer and fluorescence-sensing mechanisms of [2-(2-hydroxy-phenyl)-1H-benzoimidazol-5-yl]-phenyl-methanone

doi:10.1002/jccs.201800380

	The investigation of proton transfer and fluorescence-sensing mechanisms of [2-(2-hydroxy-phenyl)-1H-benzoimidazol-5-yl]-phenyl-methanone
	Yang, Dapeng 2,3; Zhao, Zhongjian 1; Jia, Min 3; Song, Xiaoyan 3; Zhang, Qiaoli 3; Zhang, Tianjie 3
刊名	JOURNAL OF THE CHINESE CHEMICAL SOCIETY
	2019-06-01
卷号	66 期号:6 页码:583-588
关键词	deprotonation fluoride-triggered fluorescence response intra and interhydrogen bonds potential energy curves
ISSN号	0009-4536
DOI	10.1002/jccs.201800380
通讯作者	Yang, Dapeng(dpyang_ncwu@163.com)
英文摘要	Given the tremendous potential of fluorescence sensors in recent years, in this present work, we theoretically explore a novel fluorescence chemosensor [2-(2-Hydroxy-phenyl)-1H-benzoimidazol-5-yl]-phenyl-methanone (HBPM) about its excited state behaviors and probe-response mechanism. Using density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods, we explore the S-0-state and S-1-state hydrogen bond dynamical behaviors and confirm that the strengthening intramolecular hydrogen bond in the S-1 state may promote the excited state intramolecular proton transfer (ESIPT) reaction. In view of the photoexcitation process, we find that the charge redistribution around the hydroxyl moiety plays important roles in providing driving force for ESIPT. And the constructed potential energy curves further verify that the ESIPT process of HBPM should be ultrafast. That is the reason why the normal HBPM fluorescence cannot be detected in previous experiment. Furthermore, with the addition of fluoride anions, the exothermal deprotonation process occurs spontaneously along with the intermolecular hydrogen bond O-HMIDLINE HORIZONTAL ELLIPSISF. It reveals the uniqueness of detecting fluoride anions using HBPM molecules. As a whole, the fluoride anions inhibit the initial ESIPT process of HBPM, which results in different fluorescence behaviors. This work presents the clear ESIPT process and fluoride anion-sensing mechanism of a novel HBPM chemosensor.
资助项目	Key Scientific Research Project of Colleges and Universities of Henan Province of China[18A140023]
WOS关键词	HYDROGEN-BONDING DYNAMICS ; DENSITY-FUNCTIONAL THEORY ; EXCITED-STATE SINGLE ; CHARGE-TRANSFER ; THEORETICAL INSIGHTS ; FLUORIDE ANION ; TD-DFT ; CHEMOSENSOR ; TDDFT ; SENSOR
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000471723500002
资助机构	Key Scientific Research Project of Colleges and Universities of Henan Province of China ; Key Scientific Research Project of Colleges and Universities of Henan Province of China ; Key Scientific Research Project of Colleges and Universities of Henan Province of China ; Key Scientific Research Project of Colleges and Universities of Henan Province of China ; Key Scientific Research Project of Colleges and Universities of Henan Province of China ; Key Scientific Research Project of Colleges and Universities of Henan Province of China ; Key Scientific Research Project of Colleges and Universities of Henan Province of China ; Key Scientific Research Project of Colleges and Universities of Henan Province of China
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/176100]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Yang, Dapeng
作者单位	1.North China Univ Water Resources & Elect Power, Off Teaching Affairs, Zhengzhou, Henan, Peoples R China 2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian, Peoples R China 3.North China Univ Water Resources & Elect Power, Coll Phys & Elect, Zhengzhou 450046, Henan, Peoples R China
推荐引用方式 GB/T 7714	Yang, Dapeng,Zhao, Zhongjian,Jia, Min,et al. The investigation of proton transfer and fluorescence-sensing mechanisms of [2-(2-hydroxy-phenyl)-1H-benzoimidazol-5-yl]-phenyl-methanone[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY,2019,66(6):583-588.
APA	Yang, Dapeng,Zhao, Zhongjian,Jia, Min,Song, Xiaoyan,Zhang, Qiaoli,&Zhang, Tianjie.(2019).The investigation of proton transfer and fluorescence-sensing mechanisms of [2-(2-hydroxy-phenyl)-1H-benzoimidazol-5-yl]-phenyl-methanone.JOURNAL OF THE CHINESE CHEMICAL SOCIETY,66(6),583-588.
MLA	Yang, Dapeng,et al."The investigation of proton transfer and fluorescence-sensing mechanisms of [2-(2-hydroxy-phenyl)-1H-benzoimidazol-5-yl]-phenyl-methanone".JOURNAL OF THE CHINESE CHEMICAL SOCIETY 66.6(2019):583-588.