Excited-state proton transfer of 4-hydroxyl-1, 8-naphthalimide derivatives: A combined experimental and theoretical investigation

doi:10.1016/j.jlumin.2016.04.030

	Excited-state proton transfer of 4-hydroxyl-1, 8-naphthalimide derivatives: A combined experimental and theoretical investigation
	Qu, Zongjin; Li, Peng; Zhang, Xuexiang; Wang, Endong; Wang, Yanni; Zhou, Panwang
刊名	JOURNAL OF LUMINESCENCE
	2016-09-01
卷号	177 页码:197-203
关键词	Naphthalimide Excited-state Proton Transfer Photoacid Contact Ion Pair Time-dependent Density Functional Theory
ISSN号	0022-2313
DOI	10.1016/j.jlumin.2016.04.030
文献子类	Article
英文摘要	The photophysical properties of N-butyl-4-hydroxyl-1, 8-naphthalimide (BOH) and N-(morpholinoethyl) - 4-hydroxy-1, 8-naphthalimide (MOH) in various solvents are presented and the density functional theory (DFT)/time-dependent density functional theory (TDDFT) methods at the B3LYP/TZVP theoretical level are adopted to investigate the UV-visible absorption and emission data. An efficient intermolecular excited-state proton transfer (ESPT) reaction occurs for both compounds in DMSO, methanol and water. In aqueous solution, both BOH and MOH can be used as ratiometric pH probes and perform as strong photoacids with pKa*= -2.2, -2.4, respectively. Most interestingly, in the steady-state fluorescence spectra of BOH and MOH in concentrated HCl, an unexpected blue-shifted band is observed and assumed to originate from the contact ion pair (CIP) formed by hydronium ion and the anionic form of the photoacid resulted from ESPT. Theoretical calculations are used to simulate the CIP in the case of BOH, which afford reasonable results compared with the experimental data. (c) 2016 Elsevier B.V. All rights reserved.
WOS关键词	RATIOMETRIC FLUORESCENT-PROBE ; IMAGING HYDROGEN-SULFIDE ; LARGE EMISSION SHIFT ; LIVING CELLS ; 1,8-NAPHTHALIMIDE DERIVATIVES ; FAST-RESPONSE ; PEROXIDE ; CHEMODOSIMETER ; DYNAMICS ; SOLVENTS
WOS研究方向	Optics
语种	英语
出版者	ELSEVIER SCIENCE BV
WOS记录号	WOS:000377997700030
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/170558]
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	Zhou, Panwang
作者单位	Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian, Peoples R China
推荐引用方式 GB/T 7714	Qu, Zongjin,Li, Peng,Zhang, Xuexiang,et al. Excited-state proton transfer of 4-hydroxyl-1, 8-naphthalimide derivatives: A combined experimental and theoretical investigation[J]. JOURNAL OF LUMINESCENCE,2016,177:197-203.
APA	Qu, Zongjin,Li, Peng,Zhang, Xuexiang,Wang, Endong,Wang, Yanni,&Zhou, Panwang.(2016).Excited-state proton transfer of 4-hydroxyl-1, 8-naphthalimide derivatives: A combined experimental and theoretical investigation.JOURNAL OF LUMINESCENCE,177,197-203.
MLA	Qu, Zongjin,et al."Excited-state proton transfer of 4-hydroxyl-1, 8-naphthalimide derivatives: A combined experimental and theoretical investigation".JOURNAL OF LUMINESCENCE 177(2016):197-203.