A DFT/TDDFT Investigation of Excited State Dynamical Mechanism of (E)-1-((2,2-Diphenylhydrazono)methyl)naphthalen-2-ol

doi:10.1002/jccs.201700226

	A DFT/TDDFT Investigation of Excited State Dynamical Mechanism of (E)-1-((2,2-Diphenylhydrazono)methyl)naphthalen-2-ol
	Yang, Dapeng 1,3; Wu, Jingyuan 2; Jia, Min 1; Song, Xiaoyan 1
刊名	JOURNAL OF THE CHINESE CHEMICAL SOCIETY
	2017-12-01
卷号	64 期号:12 页码:1385-1391
关键词	Electronic Spectra Frontier Molecular Orbitals Excited-state Intramolecular Proton Transfer Potential Energy Surface
ISSN号	0009-4536
DOI	10.1002/jccs.201700226
文献子类	Article
英文摘要	The excited-state intramolecular proton transfer (ESIPT) mechanism of a new compound (E)-1-((2,2-diphenylhydrazono)methyl)naphthalen-2-ol (EDMN) sensor, reported and synthesized by Mukherjee et al. [Sensors Actuat. B-Chem. 2014, 202, 1190], is investigated in detail theoretically. The calculations on primary bond lengths, bond angles, and the corresponding infrared (IR) vibrational spectra and hydrogen-bond energy involved in intramolecular hydrogen bond between the S-0 and S-1 states confirm that the intramolecular hydrogen bond is strengthened in the S-1 state, which reveals the tendency of ESIPT reaction. The fact that the experimental absorption and emission spectra are well reproduced demonstrates the rationality and effectiveness of the time-dependent density functional theory (TDDFT) level of theory we adopt here. Furthermore, intramolecular charge transfer based on the frontier molecular orbitals (MOs) gives indication of the ESIPT reaction. The constructed potential energy curves of both the S-0 and S-1 states while keeping the OH distance of EDMN fixed at a series of values are used to illustrate the ESIPT process. The lower barrier of similar to 3.934 kcal/mol in the S-1 state potential energy curve (lower than the 8.254 kcal/mol in the S-0 state) provides the transfer mechanism.
WOS关键词	DENSITY-FUNCTIONAL THEORY ; INTRAMOLECULAR CHARGE-TRANSFER ; PROTON-TRANSFER MECHANISMS ; HYDROGEN-BONDING DYNAMICS ; RAMAN-SPECTROSCOPY ; AB-INITIO ; FLUORESCENCE ; SOLVENTS ; METHANOL ; DERIVATIVES
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000418159200001
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/168380]
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 450046, Henan, Peoples R China 2.Measurement & Testing Inst Mongolian Autonomous C, Fuxing 123100, Peoples R China 3.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam Theoret & Computat, Dalian 116023, Peoples R China
推荐引用方式 GB/T 7714	Yang, Dapeng,Wu, Jingyuan,Jia, Min,et al. A DFT/TDDFT Investigation of Excited State Dynamical Mechanism of (E)-1-((2,2-Diphenylhydrazono)methyl)naphthalen-2-ol[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY,2017,64(12):1385-1391.
APA	Yang, Dapeng,Wu, Jingyuan,Jia, Min,&Song, Xiaoyan.(2017).A DFT/TDDFT Investigation of Excited State Dynamical Mechanism of (E)-1-((2,2-Diphenylhydrazono)methyl)naphthalen-2-ol.JOURNAL OF THE CHINESE CHEMICAL SOCIETY,64(12),1385-1391.
MLA	Yang, Dapeng,et al."A DFT/TDDFT Investigation of Excited State Dynamical Mechanism of (E)-1-((2,2-Diphenylhydrazono)methyl)naphthalen-2-ol".JOURNAL OF THE CHINESE CHEMICAL SOCIETY 64.12(2017):1385-1391.