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.
Synthesis and Density Functional Theory Studies of Pyridinyl hydrazide-Tethered Fused Thiazine
Gokulakrishnan, Kannan,Padmavathy, Krishnaraj,Ramalingan, Chennan,Saravanan, Vadivel,Sugunadevi, Ayyanar
, p. 479 - 487 (2021/11/22)
Synthesis of pyridinyl hydrazide-tethered fused thiazine 6 has been accomplished by adopting multistep synthetic strategy and its structure has been established based on analytical and spectroscopic techniques. Density functional theory (DFT) studies of the molecule 6 have been performed employing DFT-B3LYP method with 6-311++G(d,p) basis set. Vibrational analysis and ultraviolet-visible spectral analysis results obtained from DFT studies have been found to correlate well with the ones obtained experimentally. To determine the energetic behavior of the synthesized compound, Mulliken population analysis has been carried out. To anticipate the location of electrostatic potentials and related properties of the same, molecular electrostatic potential analysis has been made. Besides, to have an idea about the charge transfer interface within the molecule, highest occupied molecular orbital and lowest unoccupied molecular orbital analyses have been performed.
Phenothiazine and diphenylsulfone-based donor–acceptor π-systems exhibiting remarkable mechanofluorochromism
Feng, Xiucun,Fu, Shengjie,Huang, Qian,Liu, Xingliang,Xu, Defang,Zhang, Weidong,Zhang, Zhan,Zhou, Hongke
, (2020/10/02)
Two donor–acceptor luminophores PTZ-DPS and BPTZ-DPS, which are constructed by electron-donor phenothiazine and electron-acceptor diphenylsulfone moiety, are designed and synthesized. Through the effective combination of phenothiazine and diphenylsulfone unit, PTZ-DPS and BPTZ-DPS molecules adopt twisted molecular conformation, unique intramolecular charge transfer (ICT) behavior and intense fluorescence in both solution and solid state. The solid-state luminescence efficiencies of the two luminophores reach 32.84% and 39.69%, respectively. It is particularly noteworthy that both PTZ-DPS and BPTZ-DPS exhibit switchable mechanofluorochromism with high contrast. Upon external force stimulation, the fluorescence colors of the PTZ-DPS and BPTZ-DPS solid powders that change dramatically from initial bright green and yellow to orange, respectively, are observed. Meanwhile, the emission bands red shift from 499 nm to 564 nm–589 nm and 592 nm, respectively, suggesting the large spectral red shifts of 90 nm and 28 nm. Moreover, the mechanofluorochromic (MFC) behavior of PTZ-DPS and BPTZ-DPS also show good reversibility when fume the ground powders by DCM vapor. PXRD and spectral data suggest that the phase transition between crystalline to amorphous states is responsible for MFC behavior of PTZ-DPS and BPTZ-DPS, and the red-shift in the PL spectrum upon grinding originates from the planarization of the molecular conformation and subsequent planar intramolecular charge transfer (PICT).
