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Elucidating the Structure-Reactivity Correlations of Phenothiazine-Based Fluorescent Probes toward ClO-
Wang, Shichao1; Zhang, Boyu1; Wang, Wenjing2; Feng, Gang1; Yuan, Daqiang2; Zhang, Xuanjun1
2018-06-07
Source PublicationCHEMISTRY-A EUROPEAN JOURNAL
ISSN0947-6539
Volume24Issue:32Pages:8157-8166
Abstract

In this work, with the aim of developing effective molecular probes and investigating the structure-reactivity correlation, a short series of phenothiazine-based fluorescent probes are designed for the detection of ClO- with differing electron push-pull groups. Sensing experiment results and single-crystal X-ray analysis with the aid of time-dependent DFT (TD-DFT) calculations reveal that substituting groups with increasing electron-withdrawing ability can increase the dihedral angle of the phenothiazine moiety and reduce the gap energy of the probes, leading to enhanced reactivity toward ClO-. Both PT1 and PT2 show two-color switching upon detection of ClO-. PT1, with the strong electron-donating group thiophene, shows a fluorescence color switch from salmon to blue. PT2, with a medium electron-donating/accepting group benzothiazole, shows a fluorescence color switch from red to green. However, both PT1 and PT2 show almost no response to ONOO-. Through the introduction of strong electron-withdrawing ketone combined with a cyano group, PT3 shows a cyan emission upon detection of ClO- and weak red emission upon detection of ONOO-. HRMS and (HNMR)-H-1 results confirm that PT1 and PT2 have the same sensing mode, in which the divalent sulfur of phenothiazine can be oxidized to sulfoxide by ClO-. Upon reaction with ClO-, PT3 experiences two-step reactions. It is first oxidized into the sulfone structure by ClO-, and then transformed into sulfoxide phenothiazine aldehyde. Upon encountering ONOO-, PT3 changes into an aldehyde structure and some nonfluorescent byproducts. Owing to their special selectivity and high sensitivity, PT1 and PT2 are applied to image the endogenous ClO- in macrophage cells and zebrafish larvae. This study is expected to provide useful guidelines for probe design for various applications.

KeywordDensity Functional Calculations Fluorescent Probes Hypochlorous Acid Imaging Phenothiazine
DOI10.1002/chem.201800356
URLView the original
Indexed BySCI ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000437268400020
PublisherWILEY-V C H VERLAG GMBH
The Source to ArticleWOS
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Cited Times [WOS]:3   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionFaculty of Health Sciences
Affiliation1.Universidade de Macau
2.State Key Laboratory of Structural Chemistry, Fuzhou
Recommended Citation
GB/T 7714
Wang, Shichao,Zhang, Boyu,Wang, Wenjing,et al. Elucidating the Structure-Reactivity Correlations of Phenothiazine-Based Fluorescent Probes toward ClO-[J]. CHEMISTRY-A EUROPEAN JOURNAL,2018,24(32):8157-8166.
APA Wang, Shichao,Zhang, Boyu,Wang, Wenjing,Feng, Gang,Yuan, Daqiang,&Zhang, Xuanjun.(2018).Elucidating the Structure-Reactivity Correlations of Phenothiazine-Based Fluorescent Probes toward ClO-.CHEMISTRY-A EUROPEAN JOURNAL,24(32),8157-8166.
MLA Wang, Shichao,et al."Elucidating the Structure-Reactivity Correlations of Phenothiazine-Based Fluorescent Probes toward ClO-".CHEMISTRY-A EUROPEAN JOURNAL 24.32(2018):8157-8166.
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