Elaborating the excited state behavior of 2-(4-N,N-dimethylaminophenyl)-imidazo[4,5-c]pyridine coupling with methanol solvent

doi:10.1002/poc.3781

	Elaborating the excited state behavior of 2-(4-N,N-dimethylaminophenyl)-imidazo[4,5-c]pyridine coupling with methanol solvent
	Yang, Dapeng 1,2; Jia, Min 1; Song, Xiaoyan 1; Zhang, Qiaoli 1
刊名	JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
	2018-03-01
卷号	31 期号:3
关键词	Electronic Spectra Hydrogen Bond Ir Spectra Potential Energy Curves
ISSN号	0894-3230
DOI	10.1002/poc.3781
文献子类	Article
英文摘要	We present a theoretical investigation about the excited state dynamical mechanism of 2-(4-N,N-dimethylaminophenyl)-imidazo[4,5-c]pyridine (DMAPIP-c). Within the framework of density functional theory and time-dependent density functional theory methods, we reasonably repeat the experimental electronic spectra, which further confirm the theoretical level used in this work is feasible. Given the best complex model, 3 methanol (MeOH) solvent molecules should be connected with DMAPIP-c forming DMAPIP-c-MeOH complex in both ground state and excited state. Exploring the changes about bond lengths and bond angles involved in hydrogen bond wires, we find the O7-H8N9 one should be largely strengthened in the S-1 state, which plays an important role in facilitating the excited state intermolecular proton transfer (ESIPT) process. In addition, the analyses about infrared vibrational spectra also confirm this conclusion. The redistribution about charges distinguished via frontier molecular orbitals based on the photoexcitation, we do find tendency of ESIPT reaction due to the most charges located around N9 atom in the lowest unoccupied molecular orbital. Based on constructing the potential energy curves of both S-0 and S-1 states, we not only confirm that the ESIPT process should firstly occur along with hydrogen bond wire O7-H8N9, but also find a low potential energy barrier 8.898kcal/mol supports the ESIPT reaction in the S-1 state forming DMAPIP-c-MeOH-PT configuration. Subsequently, DMAPIP-c-MeOH-PT could twist its dimethylamino moiety with a lower barrier 3.475kcal/mol forming DMAPIP-c-MeOH-PT-TICT structure. Our work not only successfully explains previous experimental work but also paves the way for the further applications about DMAPIP-c sensor in future.
WOS关键词	DOUBLE-PROTON-TRANSFER ; INTRAMOLECULAR CHARGE-TRANSFER ; DENSITY-FUNCTIONAL THEORY ; PHOTOINDUCED ELECTRON-TRANSFER ; HYDROGEN-BOND ; TRANSFER MECHANISMS ; ANISOTROPIC DIELECTRICS ; SENSING MECHANISM ; SINGLE ; RELAY
WOS研究方向	Chemistry
语种	英语
出版者	WILEY
WOS记录号	WOS:000425734500010
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/168804]
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, Coll Math & Informat Sci, Zhengzhou, Henan, Peoples R China 2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
推荐引用方式 GB/T 7714	Yang, Dapeng,Jia, Min,Song, Xiaoyan,et al. Elaborating the excited state behavior of 2-(4-N,N-dimethylaminophenyl)-imidazo[4,5-c]pyridine coupling with methanol solvent[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY,2018,31(3).
APA	Yang, Dapeng,Jia, Min,Song, Xiaoyan,&Zhang, Qiaoli.(2018).Elaborating the excited state behavior of 2-(4-N,N-dimethylaminophenyl)-imidazo[4,5-c]pyridine coupling with methanol solvent.JOURNAL OF PHYSICAL ORGANIC CHEMISTRY,31(3).
MLA	Yang, Dapeng,et al."Elaborating the excited state behavior of 2-(4-N,N-dimethylaminophenyl)-imidazo[4,5-c]pyridine coupling with methanol solvent".JOURNAL OF PHYSICAL ORGANIC CHEMISTRY 31.3(2018).