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Solvatochromic Fluorescence Emission of an Anthranol Derivative without Typical Donor-Acceptor Structure: An Experimental and Theoretical Study
Alternative TitleJ. Phys. Chem. C
Zhang, Jian1; Zhao, Chongyang2; Liu, Heng1; Lv, Yanlin1; Liu, Rongji3; Zhang, Shuangshuang3; Chen, Hui2; Zhang, Guangjin3; Tian, Zhiyuan1
2015-02-05
Source PublicationJOURNAL OF PHYSICAL CHEMISTRY C
ISSN1932-7447
Volume119Issue:5Pages:2761-2769
AbstractAn anthranol derivative (DTDDP) and an anthraquinone derivative diastereomer (DDDP) without typical donor-acceptor (D-A) structural features were synthesized from 1,4-diaminoanthraquinone via a one-step reaction. The absorption and fluorescence emission properties of DTDDP and DDDP were investigated in common organic solvents with different polarity. In spite of a lack of apparent D-A structure, DTDDP exhibited apparent solvatochromic fluorescence emission with shift >80 nm in aprotic media. The linear correlation of the Stokes shift of DTDDP in a Lippert-Mataga plot was observed, and the change in the dipole moment of DTDDP upon excitation, 10.7 D, was determined. Time-dependent density functional theory (TDDFT) calculation confirmed the marked hole-electron separation of the excited DTDDP molecule as compared to that of the excited DDDP molecule. The experimental results and the theoretical calculation revealed the excited-state intramolecular charge-transfer nature of the emitting state of DTDDP molecules, which is responsible for the observed solvatochromic fluorescence emission features. The photooxidation-mediated facile conversion of DTDDP to its anthraquinone form counterpart DDDP was also confirmed.; An anthranol derivative (DTDDP) and an anthraquinone derivative diastereomer (DDDP) without typical donor-acceptor (D-A) structural features were synthesized from 1,4-diaminoanthraquinone via a one-step reaction. The absorption and fluorescence emission properties of DTDDP and DDDP were investigated in common organic solvents with different polarity. In spite of a lack of apparent D-A structure, DTDDP exhibited apparent solvatochromic fluorescence emission with shift >80 nm in aprotic media. The linear correlation of the Stokes shift of DTDDP in a Lippert-Mataga plot was observed, and the change in the dipole moment of DTDDP upon excitation, 10.7 D, was determined. Time-dependent density functional theory (TDDFT) calculation confirmed the marked hole-electron separation of the excited DTDDP molecule as compared to that of the excited DDDP molecule. The experimental results and the theoretical calculation revealed the excited-state intramolecular charge-transfer nature of the emitting state of DTDDP molecules, which is responsible for the observed solvatochromic fluorescence emission features. The photooxidation-mediated facile conversion of DTDDP to its anthraquinone form counterpart DDDP was also confirmed.
KeywordIntramolecular Charge-transfer Aggregation-induced Emission Light-emitting-diodes 2-photon Absorption Solar-cells Photophysics Polymers
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences ; Technology
DOI10.1021/jp511264r
URL查看原文
Indexed BySCI
Language英语
WOS KeywordINTRAMOLECULAR CHARGE-TRANSFER ; AGGREGATION-INDUCED EMISSION ; LIGHT-EMITTING-DIODES ; 2-PHOTON ABSORPTION ; SOLAR-CELLS ; PHOTOPHYSICS ; POLYMERS
WOS Research AreaChemistry ; Science & Technology - Other Topics ; Materials Science
WOS SubjectChemistry, Physical ; Nanoscience & Nanotechnology ; Materials Science, Multidisciplinary
WOS IDWOS:000349136400057
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Cited Times:12[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/11890
Collection研究所(批量导入)
Affiliation1.UCAS, Sch Chem & Chem Engn, Beijing 100049, Peoples R China
2.Chinese Acad Sci, Inst Chem, Key Lab Photochem, BNLMS, Beijing 100190, Peoples R China
3.Chinese Acad Sci, Inst Proc Engn, Beijing Key Lab Ion Liquids Clean Proc, Key Lab Green Proc & Engn, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Zhang, Jian,Zhao, Chongyang,Liu, Heng,et al. Solvatochromic Fluorescence Emission of an Anthranol Derivative without Typical Donor-Acceptor Structure: An Experimental and Theoretical Study[J]. JOURNAL OF PHYSICAL CHEMISTRY C,2015,119(5):2761-2769.
APA Zhang, Jian.,Zhao, Chongyang.,Liu, Heng.,Lv, Yanlin.,Liu, Rongji.,...&Tian, Zhiyuan.(2015).Solvatochromic Fluorescence Emission of an Anthranol Derivative without Typical Donor-Acceptor Structure: An Experimental and Theoretical Study.JOURNAL OF PHYSICAL CHEMISTRY C,119(5),2761-2769.
MLA Zhang, Jian,et al."Solvatochromic Fluorescence Emission of an Anthranol Derivative without Typical Donor-Acceptor Structure: An Experimental and Theoretical Study".JOURNAL OF PHYSICAL CHEMISTRY C 119.5(2015):2761-2769.
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