Concerted Mechanisms of Excited-State Proton Intramolecular Transfer for Bis-2,4-(2-benzoxazolyl)-hydroquinone and Its Derivatives

	Concerted Mechanisms of Excited-State Proton Intramolecular Transfer for Bis-2,4-(2-benzoxazolyl)-hydroquinone and Its Derivatives
	Yang, Chuanlu 1; Wang, Meishan 1; Bao, Dongshuai 1; Ma, Xiaoguang 1; Yang, Yunfan 2
刊名	JOURNAL OF PHYSICAL CHEMISTRY A
	2017-11-02
卷号	121 期号:43 页码:8217-8226
英文摘要	The concerted mechanisms of excited state intramolecular proton transfer (ESIPT) of bis-2,4-(2-benzoxazolyl)-hydroquinone (BBHQ') and its derivatives (BBHQ'(-) and DHBO') have been investigated using the density functional theory (DFT) and the time-dependent density functional theory (TDDFT). The calculated absorption and emission spectra of BBHQ' and its derivatives are in good agreement with the experimental results. The calculated bond lengths, bond angles, and IR vibrational spectra linked with hydrogen bond of molecular BBHQ' in the S-0 and S-1 states demonstrate that the hydrogen bond is strengthened in the S-1 state. Compared to BBHQ', BBHQ'(-) has a weak change of hydrogen bond between the S-1 and S-0 states. The calculation results show that there are three stable structures of BBHQ in the S-1 state. We find that the structure corresponding to the 481 nm fluorescence spectrum corresponds to BBHQ'-A rather than BBHQ'-K (Tetrahedron Lett., 2016, 57, 3518). The calculated frontier molecular orbitals (MOs) indicate the nature of the charge distribution and the trend of proton transfer of BBHQ'-A. The constructed potential energy surfaces of BBHQ and DBHO' further elucidate the proposed mechanism that one-proton or two-proton transfer can happen (stepwise or synchronous) in the S-1 states. The proposed ESIPT mechanism can provide a good explanation of the phenomenon of fluorescence quenching of BBHQ and its derivatives. Finally, the weak interaction types are discriminated through the reduced density gradient (RDG) analyses of BBHQ., and BBHQ'(-).
WOS标题词	Science & Technology ; Physical Sciences
类目[WOS]	Chemistry, Physical ; Physics, Atomic, Molecular & Chemical
研究领域[WOS]	Chemistry ; Physics
关键词[WOS]	TRANSITION-STATES ; BORATE COMPLEXES ; HYDROXIDE IONS ; DYNAMICS ; BENZOXAZOLE ; DENSITY ; SENSOR ; WATER ; 6-HYDROXYQUINOLINE ; PHOTOCHEMISTRY
收录类别	SCI
语种	英语
WOS记录号	WOS:000414622800006
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/149711]
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
作者单位	1.Ludong Univ, Sch Phys & Optoelect Engn, Yantai 264025, 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, Chuanlu,Wang, Meishan,Bao, Dongshuai,et al. Concerted Mechanisms of Excited-State Proton Intramolecular Transfer for Bis-2,4-(2-benzoxazolyl)-hydroquinone and Its Derivatives[J]. JOURNAL OF PHYSICAL CHEMISTRY A,2017,121(43):8217-8226.
APA	Yang, Chuanlu,Wang, Meishan,Bao, Dongshuai,Ma, Xiaoguang,&Yang, Yunfan.(2017).Concerted Mechanisms of Excited-State Proton Intramolecular Transfer for Bis-2,4-(2-benzoxazolyl)-hydroquinone and Its Derivatives.JOURNAL OF PHYSICAL CHEMISTRY A,121(43),8217-8226.
MLA	Yang, Chuanlu,et al."Concerted Mechanisms of Excited-State Proton Intramolecular Transfer for Bis-2,4-(2-benzoxazolyl)-hydroquinone and Its Derivatives".JOURNAL OF PHYSICAL CHEMISTRY A 121.43(2017):8217-8226.