18413-61-1Relevant articles and documents
Synthesis and properties of imidazole-p-phenothiazine derivatives as light-emitting and ambipolar materials
Shao, Jing,Zhao, Xin,He, Xing,Zhang, Zhengyin,Zhai, Rongjia
, p. 1637 - 1640 (2014)
Novel phenothiazine derivatives were designed and synthesized for application as electroluminescent materials. They were characterized by means of 1H, 13C NMR and FTIR. The optical, electrochemical and thermal properties were also investigated. The relati
Elucidating the Structure–Reactivity Correlations of Phenothiazine-Based Fluorescent Probes toward ClO?
Wang, Shichao,Zhang, Boyu,Wang, Wenjing,Feng, Gang,Yuan, Daqiang,Zhang, Xuanjun
, p. 8157 - 8166 (2018)
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 1H NMR 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.
Switching photorelease to singlet oxygen generation by oxygen functionalization of phenothiazine photocages
Anoop, Anakuthil,Banerjee, Moumita,Ojha, Mamata,Ray, Souvik,Singh, Amit Kumar,Singh, N. D. Pradeep
supporting information, p. 2754 - 2757 (2022/03/07)
A phenothiazine-based photoremovable protecting group (PRPG) for single and dual release of carboxylic acids was developed. The change in the oxidation state of the sulfur atom of the phenothiazine PRPG resulted in singlet oxygen generation, rather than photorelease. The difference in the photochemistry between oxygen-free and oxygen-functionalized phenothiazine was investigated and supported by DFT calculations.
Design synthesis and property research based on phenothiazine reversible fluorescent probe
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Paragraph 0018; 0020, (2021/12/07)
The invention relates to the field of fluorescent probes, and provides a fluorescent probe capable of good selectivity GSH, in particular to a fluorescent probe which takes phenothiazine as a light emitting group and reacts with a Michael reaction acceptor - active double bond as a reaction site to synthesize a reversible specific identification GSH. The structural formula is as follows. The fluorescent probe of the present invention has high selectivity and sensitivity for GSH, a 1% DMSO (PBS) buffer solution containing pH=7.4, a probe (10 μm) pair Cys (200 μm). Hcy (15 μm) And GSH (5 mm) In response 35 min, the probe can have good selectivity for GSH through ultraviolet and fluorescence spectrometer detection results. In response to GSH different concentrations, as GSH concentration increases, the fluorescence emission intensity gradually decreases at 606 nm, fluorescence emission intensity and GSH concentration are in a linear relation in a certain range, and the fluorescence probe has the advantages of high GSH action speed, strong selectivity, high sensitivity, simple synthesis method, easily available raw materials and easiness in popularization.
Development of an ultrasensitive Ru(II) complex-based fluorescent probe with phenothiazine unit for selective detection HOCl and its application in water samples
Zhang, Jiulong,Zhang, Daobin,Xiao, Lin,Pu, Shouzhi
, (2021/02/03)
A near-infrared probe Ru-1 with a phenothiazine derivative moiety as a responsive unit was designed to sensitively and selectively recognize HOCl in pure PBS solution. Upon addition of HOCl to a PBS solution of Ru-1, S-atom of the phenothiazine unit oxidized to sulfoxide, accompanied with a marked fluorescence enhancement about 60 fold at 635 nm. Probe Ru-1 displayed excellent water-solubility (PBS solution), low detection limit (4.4 nM), long fluorescence lifetime (354.36 ns) and large Stokes shift (175 nm). The experiments of its quantitative detection HOCl in water samples implied the probe Ru-1 possessed potential application in the environment.
