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Theoretical Investigation of an Excited-State Intramolecular Proton-Transfer Mechanism for an Asymmetric Structure of 3,7-Dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde: Single or Double?
Tang, Zhe1,2; Wang, Yi1; Bao, Dongshuai2; Lv, Meiheng2; Yang, Yi3; Tian, Jing1; Dong, Liang1
Source PublicationJOURNAL OF PHYSICAL CHEMISTRY A
2017-11-23
ISSN1089-5639
DOI10.1021/acs.jpca.7b08266
Volume121Issue:46Pages:8807-8814
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Physical ; Physics, Atomic, Molecular & Chemical
WOS Research AreaChemistry ; Physics
WOS KeywordDENSITY-FUNCTIONAL THEORY ; RAMAN-SPECTROSCOPY ; TRANSFER KINETICS ; 3-HYDROXYFLAVONE ; FLUORESCENCE ; DYNAMICS ; DESIGN ; PROBE ; CHROMOPHORES ; PHOTOPHYSICS
Abstract3,7-Dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde in methylcyclohexane solvent was chosen to investigate excited-state intramolecular proton-transfer mechanisms by using a time-dependent density functional theory method. The results show that the single- and double-proton transfer mechanisms are related and exist simultaneously in the excited states, which differs from those reported in previous experiments (Serdiuk, I. E. et al. RSC Adv. 2015, S, 102191-102203). The analyses of bond distance, bond angle, the molecular electrostatic potential surface, and infrared-vibrational spectra show that two intramolecular hydrogen bonds were formed in the S-0 (s)tate, and upon excitation, the two intramolecular hydrogen bonds were strengthened in the S-1 state, which can facilitate the proton-transfer process. The calculated absorption and fluorescence spectra agree well with the experimental results. The constructed potential energy surfaces on the S-1 and S-0 states can explain the proton-transfer process. In the S1 state, three types of proton-transfer processes exist as type 1 (single-proton transfer: H-2 from O-1 to O-3), type 2 (single proton transfer: H-S from O-4 to O-6), and type 3 (double-proton transfer). The relationship of the potential barrier is type 1 (1.02 kcal/mol) < type 2 (1.57 kcal/mol) < type 3 (2.29 kcal/mol), which indicates that type 1 is most susceptible to proton transfer.
Language英语
WOS IDWOS:000416495300008
PublisherAMER CHEMICAL SOC
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/169277
Collection中国科学院大连化学物理研究所
Corresponding AuthorWang, Yi
Affiliation1.Dalian Polytech Univ, Sch Biol Engn, Dalian 116034, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
3.Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian 116034, Peoples R China
Recommended Citation
GB/T 7714
Tang, Zhe,Wang, Yi,Bao, Dongshuai,et al. Theoretical Investigation of an Excited-State Intramolecular Proton-Transfer Mechanism for an Asymmetric Structure of 3,7-Dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde: Single or Double?[J]. JOURNAL OF PHYSICAL CHEMISTRY A,2017,121(46):8807-8814.
APA Tang, Zhe.,Wang, Yi.,Bao, Dongshuai.,Lv, Meiheng.,Yang, Yi.,...&Dong, Liang.(2017).Theoretical Investigation of an Excited-State Intramolecular Proton-Transfer Mechanism for an Asymmetric Structure of 3,7-Dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde: Single or Double?.JOURNAL OF PHYSICAL CHEMISTRY A,121(46),8807-8814.
MLA Tang, Zhe,et al."Theoretical Investigation of an Excited-State Intramolecular Proton-Transfer Mechanism for an Asymmetric Structure of 3,7-Dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde: Single or Double?".JOURNAL OF PHYSICAL CHEMISTRY A 121.46(2017):8807-8814.
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