117850-52-9

Usage

Uses

Used in Pharmaceutical Industry:
S2153 is used as a solvent for various pharmaceutical formulations due to its ability to dissolve a broad spectrum of substances, facilitating the creation of effective and stable medications.
Used in Personal Care Products:
In the personal care industry, S2153 is used as a solvent and plasticizer to improve the texture and consistency of products, ensuring they are both effective and pleasant to use.
Used in Industrial Applications:
S2153 is utilized as a solvent and plasticizer in industrial settings to enhance the properties of various materials, contributing to the production of high-quality goods.

Upstream product

• 20893-30-5 2-cyanomethylthiophene 
• 17754-90-4 4-(Diethylamino)salicylaldehyde 
• 1918-77-0 Thiophene-2-acetic acid 
• 6165-68-0 thiophene boronic acid 
• 133590-13-3 3-bromo-7-(diethylamino)-2H-chromen-2-one 
• 20571-42-0 7-diethylamino-2H-benzopyran-2-one 
• 64-67-5 diethyl sulfate 

Downstream Products

• 1447841-39-5 C₅₁H₇₅NO₂P₂PtS 

Relevant academic research and scientific papers

Investigation of novel carbazole-functionalized coumarin derivatives as organic luminescent materials

Four new carbazole-based coumarin derivatives comprising a carbazole core and one or two coumarin chromophores, 7-(diethylamino)-3-(4-(9-(p-tolyl)-9H-carbazol-3-yl)phenyl)coumarin (Cz-Ph-C) and 3,3'-((9-(p-tolyl)-9H-carbazole-3,6-diyl)bis(4,4′-phenyl))bis

Synthesis, characterization, and properties of novel bis(aryl)carbazole-containing N-coumarin derivatives

A series of novel N-coumarin derivatives containing oligothiophene-substituted N-coumarins as the core and bis(aryl)carbazoles as the substituent were synthesized and characterized. Their optical, electrochemical, and thermal properties were investigated. The electroluminescence (EL) properties of the selected materials were also studied. Solution-processed OLEDs with green and yellow light emission, turn-on voltages of 2.7-2.9 V, and maximum luminance efficiencies of up to 3.94 cd A-1 at 17.6 mA cm-2 (maximum power efficiency of 1.62 lm W-1) were prepared.

Sectional intramolecular charge transfer manipulating in a D-A-D' coumarin derivative for recessive rewritable paper

External-stimuli-responsive rewritable paper has attracted significant attention for application in secure information. However, to encrypt information on papers which can not be read out under visible light is still challenging. In this work, recessive rewritable paper for security information handling was realized via sectional intramolecular charge transfer (SICT) manipulating in a delicately designed coumarin derivative CMNT. By rational arranging a thiophenyl group and a diethylamino group as electron donors at the 3- and 7-position of coumarin skeleton, respectively, CMNT exhibited obvious fluorescence switching upon BF3 and trimethylamine stimuli. After impregnating a filter paper into CMNT solution with low concentration (1 × 10?6 M), no color change of the paper could be observed under visible light. Meanwhile, when writing and erasing the information on the paper by BF3 ink and trimethylamine eraser, respectively, the process can only be witnessed under UV light. Studies revealed the ICT effect from diethylamino group to chromen-2-one was suppressed after adding BF3, while the ICT channel from thiophenyl group to chromen-2-one was retained, thus producing such unique phenomenon.

A Coumarin-Based Analogue of Thiacetazone as Dual Covalent Inhibitor and Potential Fluorescent Label of HadA in Mycobacterium tuberculosis

A novel coumarin-based molecule, designed as a fluorescent surrogate of a thiacetazone-derived antitubercular agent, was quickly and easily synthesized from readily available starting materials. This small molecule, coined Coum-TAC, exhibited a combination of appropriate physicochemical and biological properties, including resistance toward hydrolysis and excellent antitubercular efficiency similar to that of well-known thiacetazone derivatives, as well as efficient covalent labeling of HadA, a relevant therapeutic target to combat Mycobacterium tuberculosis. More remarkably, Coum-TAC was successfully implemented as an imaging probe that is capable of labeling Mycobacterium tuberculosis in a selective manner, with an enrichment at the level of the poles, thus giving for the first time relevant insights about the polar localization of HadA in the mycobacteria.

Synthesis, characterisation, and electroluminescence properties of N-coumarin derivatives containing peripheral triphenylamine

A series of N-coumarin derivatives, namely CThnT and CThnCT (n = 1-2), containing triphenylamine or triphenylaminesubstituted carbazole as substituent were synthesised, and their structures were confirmed by MALDITOF MS, and NMR and IR spectroscopy. Their optical, physical and electroluminescence properties as non-doped solutionprocessed light-emitters for OLEDs were investigated. DSC, TGA, AFM and PL spectra revealed their good filmforming properties, high thermal and morphological stability, and good photoluminescence characteristics. The doublelayer solution-processed OLEDs (ITO/PEDOT:PSS/EML/BCP/LiF:Al) fabricated using CThnT and CThnCT as the emissive layer and BCP as the electron-transporting and hole-blocking layer, exhibited stable green to orange electroluminescence (λEL = 536-592 nm) with turn-on voltages of 2.7-2.9 V and maximum luminance efficiencies up to 3.94 cdA-1 at 17.6 mAcm-2 (maximum power efficiency of 1.62 lmW-1).

N-coumarin derivatives as hole-transporting emitters for high efficiency solution-processed pure green electroluminescent devices

A series of new N-coumarin dyes containing oligothiophenyl N-coumarins as cores and carbazole dendrons up to the third generation as substituents were synthesized and characterized. Their optical, thermal, electrochemical, and electroluminescent properties as non-doped solution-processed hole-transporting light-emitters for electroluminescent devices were investigated. It was found that by incorporating carbazole dendrons in the molecule, we were able to reduce the crystallization and maintain the high emissive ability of a planar N-coumarin fluorescent core in the solid state as well as improve the thermal stability of the material. These N-coumarins showed a bright green fluorescence and could form morphologically stable amorphous thin films with glass-transition temperatures as high as 299 °C. Simple structured solution-processed organic light-emitting diodes using these dyes as emissive layers emitted a stable green electroluminescence (λEL = 517 nm) with high luminance efficiencies (up to 9.45 cd A-1 at 6.7 mA cm-2) and high green color purity.

Design and Synthesis of Coumarin–Imidazole Hybrid Chromophores: Solvatochromism, Acidochromism and Nonlinear Optical Properties

A set of linear and asymmetric coumarin–imidazole hybrid compounds having a N,N-diethylamine at 7-position and imidazole at 3-position on the coumarin were synthesized. Insertion of thiophene π-spacer between coumarin and imidazole moieties (5b, 5d) leads to redshifted absorption and emission compared to 5a and 5c. All the compounds show a noticeable response to trifluoroacetic acid with a redshifted absorption and an increase in emission intensity by twofold. The ratio of ground and excited state acidity constant was calculated using F?rster energy cycle, and the ratios were found to be 0.25, 0.96, 0.52 and 1.87, respectively, for 5a-5d. Due to the thiophene π-spacer, elongation of π-conjugation in 5b and 5d leads to high values of polarizability (α), first-order hyperpolarizability (β) and second-order hyperpolarizability (γ). Compound 5b exhibits a high value (895 GM) of two-photon absorption cross section (σ2PA), measured using two-level model.

3-carboxylic acid and formyl-derived coumarins as photoinitiators in photo-oxidation or photo-reduction processes for photopolymerization upon visible light: Photocomposite synthesis and 3d printing applications

In this paper, nine organic compounds based on the coumarin scaffold and different substituents were synthesized and used as high-performance photoinitiators for free radical pho-topolymerization (FRP) of meth(acrylate) functions under visible light irradiation using LED at 405 nm. In fact, these compounds showed a very high initiation capacity and very good polymerization profiles (both high rate of polymerization (Rp) and final conversion (FC)) using two and three-component photoinitiating systems based on coum/iodonium salt (0.1%/1% w/w) and coum/iodonium salt/amine (0.1%/1%/1% w/w/w), respectively. To demonstrate the efficiency of the initiation of photopolymerization, several techniques were used to study the photophysical and photochemical properties of coumarins, such as: UV-visible absorption spectroscopy, steady-state photolysis, real-time FTIR, and cyclic voltammetry. On the other hand, these compounds were also tested in direct laser write experiments (3D printing). The synthesis of photocomposites based on glass fiber or carbon fiber using an LED conveyor at 385 nm (0.7 W/cm2 ) was also examined.

Coumarins as powerful photosensitizers for the cationic polymerization of epoxy-silicones under near-UV and visible light and applications for 3D printing technology

In this study, eight coumarins (coumarins 1–8) are proposed as near-UV and blue light sensitive photoinitiators/photosensitizers for the cationic polymerization (CP) of epoxysilicones when combined with 4-isopropyl-4’-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (IOD). Among these coumarins, four of them (coumarins 1, 2, 6 and 8) have never been reported in the literature, i.e., these structures have been specifically designed to act as photoinitiators for silicones upon near UV and visible irradiation. Good final reactive epoxy function conversions (FCs) and also high rates of polymerization (Rp) were achieved in the presence of the newly proposed coumarin-based systems. The polymers generated from the photopolymerization of epoxysilicones can be considered as attractive candidates for several applications such as: elastomers, coatings, adhesives, and so on. The goal of this study focuses also on the comparison of the new proposed coumarins with well-established photosensitizers i.e., 1-chloro-4-propoxythioxanthone (CPTX), 9,10-dibutoxyanthracene (DBA) or some commercial coumarins (Com. Coum). As example of their high performance, the new proposed coumarins were also used for laser write experiments upon irradiation with a laser diode at 405 nm in order to develop new cationic 3D printing systems.

Application of coumarin dyes for organic photoredox catalysis

Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(iii)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins could be varied, a wide applicability to several classes of photoredox reactions is predicted.