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Comprehensive Studies on Excited-State Proton Transfer of a Series of 2-(2 '-Hydroxyphenyl)benzothiazole Derivatives: Synthesis, Optical Properties, and Theoretical Calculations
Cheng, Jinling1,2; Liu, Di1; Li, Wei1; Bao, Lijun1; Han, Keli2
Source PublicationJOURNAL OF PHYSICAL CHEMISTRY C
2015-02-26
DOI10.1021/jp511578v
Volume119Issue:8Pages:4242-4251
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences ; Technology
WOS SubjectChemistry, Physical ; Nanoscience & Nanotechnology ; Materials Science, Multidisciplinary
WOS Research AreaChemistry ; Science & Technology - Other Topics ; Materials Science
WOS KeywordLIGHT-EMITTING-DIODES ; INTRAMOLECULAR PROTON ; TRANSFER ESIPT ; IRIDIUM COMPLEXES ; COUPLED ELECTRON ; FLUORESCENCE ; DENSITY ; MECHANISM ; EXCHANGE ; ELECTROLUMINESCENCE
AbstractA group of novel 2-(2'-hydroxyphenyl)benzothiazole derivatives (1-4) with excited-state intramolecular proton transfer (ESIPT) character were synthesized. Their photophysical properties were studied by means of steady-state absorption and fluorescence spectra and time-resolved emission method as well as theoretical calculation in a variety of solvents. All of these compounds can yield single fluorescence at the green region in nonpolar solvents such as n-hexane, while dual fluorescence consisting of the blue and green bands was captured in strong polar solvents like acetonitrile. In addition, a third emission band between the former two bands was detected for these molecules simultaneously with the blue and green ones generating the well-structured triple fluorescence in protic solvent like ethanol. Systematical comparison of the fluorescence of these compounds in a series of solvents demonstrated that nonpolar solvents would facilitate ESIPT process and the green emission from the keto format, while the strong polar solvents impede the ESIPT process and favor the blue normal emission from enol. Protic solvents facilitate deprotonation and make the phenolic anion coexist with keto and enol and consequently lead to triple fluorescence. On the premise of identical keto emission intensity, the normal emission intensity of these compound increases consecutively in the order of increasing electron-withdrawing ability of the substituents regardless of solvents. The results of quantum-chemical calculations are well in line with the experimental spectra.
Language英语
WOS IDWOS:000350329300039
Citation statistics
Cited Times:37[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/146053
Collection中国科学院大连化学物理研究所
Affiliation1.Dalian Univ Technol, Sch Chem, State Key Lab Fine Chem, Dalian 116024, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
Recommended Citation
GB/T 7714
Cheng, Jinling,Liu, Di,Li, Wei,et al. Comprehensive Studies on Excited-State Proton Transfer of a Series of 2-(2 '-Hydroxyphenyl)benzothiazole Derivatives: Synthesis, Optical Properties, and Theoretical Calculations[J]. JOURNAL OF PHYSICAL CHEMISTRY C,2015,119(8):4242-4251.
APA Cheng, Jinling,Liu, Di,Li, Wei,Bao, Lijun,&Han, Keli.(2015).Comprehensive Studies on Excited-State Proton Transfer of a Series of 2-(2 '-Hydroxyphenyl)benzothiazole Derivatives: Synthesis, Optical Properties, and Theoretical Calculations.JOURNAL OF PHYSICAL CHEMISTRY C,119(8),4242-4251.
MLA Cheng, Jinling,et al."Comprehensive Studies on Excited-State Proton Transfer of a Series of 2-(2 '-Hydroxyphenyl)benzothiazole Derivatives: Synthesis, Optical Properties, and Theoretical Calculations".JOURNAL OF PHYSICAL CHEMISTRY C 119.8(2015):4242-4251.
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