15375-48-1

Usage

InChI:InChI=1/C15H15NS/c1-2-11-16-12-7-3-5-9-14(12)17-15-10-6-4-8-13(15)16/h3-10H,2,11H2,1H3

Upstream product

• 20962-92-9 10-allylphenothiazine 
• 92-84-2 10H-phenothiazine 
• 106-94-5 propyl bromide 
• 107-08-4 1-iodo-propane 

Relevant academic research and scientific papers

Alkyl Chain Length Effects on the Photoionization of N-Alkylphenothiazines and Sulfonated Alkylphenothiazines in Anionic Alkyl Sulfate and Cationic Alkyltrimethylammonium Bromide Micelles

The photoionization yields of N-alkylphenothiazines solubilized in either cationic or anionic micelles at 77 K were studied as a function of both alkyl and surfactant chain length.The results are compared to similar work on sulfonated N-alkylphenothiazines.The location of the phenothiazine moiety with respect to the micelle-water interface together with cation-water interactions is a major factor controlling the photoionization efficiency.The position of the N-alkylphenothiazine chromophore within a micelle can be altered by changing the alkyl chain length.The photoefficiency is also affected by the surface charge of the micelle.

NIR-Absorbing Donor–Acceptor Based 1,1,4,4-Tetracyanobuta-1,3-Diene (TCBD)- and Cyclohexa-2,5-Diene-1,4-Ylidene-Expanded TCBD-Substituted Ferrocenyl Phenothiazines

A series of unsymmetrical (D-A-D1, D1-π-D-A-D1, and D1-A1-D-A2-D1; A=acceptor, D=donor) and symmetrical (D1-A-D-A-D1) phenothiazines (4 b, 4 c, 4 c′, 5 b, 5 c, 5 d, 5 d′, 5 e, 5 e′, 5 f, and 5 f′) were designed and synthesized by a [2+2] cycloaddition–electrocyclic ring-opening reaction of ferrocenyl-substituted phenothiazines with tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ). The photophysical, electrochemical, and computational studies show a strong charge-transfer (CT) interaction in the phenothiazine derivatives that can be tuned by varying the number of TCNE/TCNQ acceptors. Phenothiazines 4 b, 4 c, 4 c′, 5 b, 5 c, 5 d, 5 d′, 5 e, 5 e′, 5 f and 5 f′ show redshifted absorption in the λ=400 to 900 nm region, as a result of a low HOMO–LUMO gap, which is supported by TD-DFT calculations. The electrochemical study exhibits reduction waves at low potential due to strong 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) and cyclohexa-2,5-diene-1,4-ylidene-expanded TCBD acceptors. The incorporation of cyclohexa-2,5-diene-1,4-ylidene-expanded TCBD stabilized the LUMO energy level to a greater extent than TCBD.

Piezofluorochromic properties of AIE-active 9,10-bis(N-alkylpheno-thiazin- 3-yl-vinyl-2)anthracenes with different length of alkyl chains

9,10-Bis(N-alkylphenothiazin-3-yl-vinyl-2)anthracenes (PT-Cn) with different carbon numbers (n) of alkyl chains (n = 2, 3, 5, 6, 7, 9, 12, 18) are prepared to further understand the effect of alkyl lengths on the solid-state fluorescence and piezochromic luminescence of alkyl-containing 9,10-bis(arylvinyl)anthracenes. The results show that the fluorescence emissions of both pressed and annealed PT-Cn are gradually blue-shifted, but the blue-shifted amplitudes of annealed states are more remarkable with the increase of alkyl length, leading to that longer alkyl-containing PT-Cn show larger piezofluorochromism (PFC) spectral shifts. Powder wide-angle X-ray diffraction and differential scanning calorimetry experiments reveal that the transformation between crystalline and amorphous states under various external stimuli is responsible for the PFC and restoration behaviors. This work demonstrates once again that combining the simple alternation of molecular chemical structure and the physical change of aggregate morphology under external stimuli could tune the solid-state optical properties of some organic fluorophores.

Photoinduced charge separation of phenothiazine derivatives in layered zirconium phosphate at room temperature

The photoionization of alkylphenothiazines in layered α-zirconium phosphate (α-ZrP or ZrP) has been studied by electron spin resonance (ESR) and diffuse reflectance spectroscopies. Alkylphenothiazines (PC(n) where n = 1, 2, 3, 4, 6, 8, 10, 16) were synthesized and used to study the effects of the alkyl chain length. Phenothiazine and N-alkylphenothiazines were incorporated into ZrP by impregnation and ion-exchange methods. By both methods N-alkylphenothiazines are only incorporated onto the external surface of zirconium phosphate rather than into the interlayer space. The alkylphenothiazines photooxidize at room temperature to form stable alkylphenothiazine cation radicals (PC(n)+) which are measured by ESR and diffuse reflectance. The framework of ZrP is suggested to be the electron acceptor. Both the photoyield and the decay rate of the alkylphenothiazine cation radical depend on the alkyl chain length. As the alkyl chain length of the PC(n)+ cation radical increases from methyl to hexyl, the photooxidation yield increases; and as the alkyl chain length increases further from hexyl to hexadecyl, the photooxidation yield decreases. However, the decay rate of the PC(n)+ cation radical gradually increases from methyl to hexadecyl which is explained in terms of a greater inductive effect for longer alkyl chains on the PC(n)+ cation radicals. Also, the resolution of the ESR spectrum decreases with increasing alkyl chain length which is interpreted as being due to decreasing mobility of the radical which should also decrease the decay rate. Both impregnation and ion-exchange methods are reasonably effective for incorporating alkylphenothiazine molecules into ZrP for efficient photooxidation. The photoyields of N-alkylphenothiazines in ZrP are larger than in silica gel which suggests that ZrP assemblies can be utilized for solar energy conversion and storage.

Photoionization of N-alkylphenothiazines in mesoporous metal silicoaluminophosphate molecular sieves

The photoionization of N-alkylphenothiazines (PCn where n = 1, 3, 6, 10, and 16) in mesoporous silicoaluminophosphate (UHM-3) and transition metal-substituted silicoaluminophosphate (MUHM-3 where M = Cu, Ni, Cr, and Mn) molecular sieves has been studied by electron spin resonance with ultraviolet irradiation at room temperature. Mesoporous UHM-3 and MUHM-3 molecular sieves were synthesized at room temperature. The effect of the ratio of Si/Al, the nature of the transition metal, and the concentration of the metal on the photoyield was examined. N-Alkylphenothiazine was incorporated into these mesoporous materials and the photoionization of PCn was studied.

Synthesis and photophysical study of novel coumarin based styryl dyes

New organic dyes comprising phenothiazine, carbazole, indole, diphenylamine moieties, as the electron donors, and coumarin ring as the electron acceptor through ethylenic π bridge were synthesized and characterized. The reaction of different coumarin-4-acetic acids with phenothiazine-3-carbaldehyde in the presence of piperidine in methanol gives highly fluorescent styryl derivatives having cis configuration of ethylenic double bond. Under similar conditions 7-methylcoumarin-4-acetic acid was condensed with indole-3-carbaldehyde, carbazole-3-carbaldehyde, and diphenyl amine aldehyde to give different styryl derivatives with trans configuration of ethylenic double bond. Synthesized compounds were also studied for photophysical properties and show solvatochromism.

Structure-activity relationship studies of phenothiazine derivatives as a new class of ferroptosis inhibitors together with the therapeutic effect in an ischemic stroke model

Ferroptosis is a new type of programmed cell death discovered recently and has been demonstrated to be involved in a number of human diseases such as ischemic stroke. Ferroptosis inhibitors are expected to have potential to treat these diseases. Herein, we report the identification of promethazine derivatives as a new type of ferroptosis inhibitors. Structure-activity relationship (SAR) analyses led to the discovery of the most potent compound 2-(1-(4-(4-methylpiperazin-1-yl)phenyl)ethyl)-10H-phenothiazine (51), which showed an EC50 (half maximal effective concentration) value of 0.0005 μM in the erastin-induced HT1080 cell ferroptosis model. In the MCAO (middle cerebral artery occlusion) ischemic stroke model, 51 presented an excellent therapeutic effect. This compound also displayed favorable pharmacokinetic properties, in particular, a good ability to permeate the blood-brain barrier. Overall, 51 could be a promising lead compound for the treatment of ferroptosis related diseases and deserves further investigations.

All-PEGylated redox-active metal-free organic molecules in non-aqueous redox flow battery

Non-aqueous organic material-based redox flow batteries (NAORFBs) possess the advantage of using organic solvents to achieve high electrochemical potential. However, regardless of the great progress made in this regard in the past decade, further development has been restricted by the lack of stable electroactive organic materials and highly selective separators. Here, we present a NAORFB with all-PEGylated, metal-free, organic compounds as electroactive materials. PEGylated phenothiazine and PEGylated viologen are utilized as the catholyte and anolyte, respectively. Combined with a composite nanoporous aramid nanofiber separator, the all-PEGylated NAORFB presents outstanding cyclability, with a capacity retention of 99.90% per cycle and average coulombic efficiency of 99.7%. By contrast, NAORFBs using half-PEGylated and non-PEGylated electrolytes display inferior cyclability owing to the crossover of non-PEGylated materials. An extended investigation was also performed on the batteries using non-PEGylated or half-PEGylated materials for mechanistic elucidation. This work validates the PEGylation strategy in NAORFBs for enhanced overall performance with respect to solubility, cyclability, and alleviated crossover. This journal is

Reversible mechanochromism and aggregation induced enhanced emission in phenothiazine substituted tetraphenylethylene

Mono and tetra phenothiazine (PTZ) functionalized tetraphenylethylene (TPE) derivatives PTZTPE-1 and PTZTPE-4 were designed and synthesized by the Suzuki cross-coupling reactions between PTZ boronate ester and bromo TPEs. The PTZTPE-1 and PTZTPE-4 are hig

Stimuli-responsive phenothiazine-based donor-acceptor isomers: AIE, mechanochromism and polymorphism

The development of solid-state stimuli responsive materials has escalated following their intriguing colour switching properties and versatile material and optoelectronic applications. In this article, we have designed and synthesized donor-acceptor (D-A)