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Practical synthesis of photochromic diarylethenes in integrated flow microreactor systems

An effective method for the synthesis of photochromic diarylethenes through the generation of heteroaryllithiums and subsequent reaction with octafluorocyclopentene has been developed by using integrated flow microreactor systems. Reactions can be conducted without using cryogenic conditions by virtue of effective temperature and residence time control, although much lower temperatures (<-78C) are needed for batch macroreactions. Moreover, the synthesis of unsymmetrical diarylethenes, which is difficult to achieve when using conventional batch macrosystems, has been accomplished based on the selective introduction of one aryl group to give arylheptafluorocyclopentene followed by the introduction of another aryl group. The productivity of the laboratory-scale system is approximately 0.5 mmolmin-1. Therefore, the present integrated flow microreactor method serves as a practical way of synthesizing various photochromic diarylethene derivatives. Too successful to be cool: An effective method for the synthesis of photochromic diarylethenes has been developed by using integrated flow microreactor systems. Reactions can be conducted without the need for cryogenic conditions by using these systems (see picture). The synthesis of unsymmetrical diarylethenes, which is difficult to achieve by using conventional macro batch systems, has also been accomplished. Copyright One of the oldest and most widely used commercial enzyme inhibitors is aspirin, Application In Synthesis of 3-Bromo-2-methylbenzo[b]thiophene, which selectively inhibits one of the enzymes involved in the synthesis of molecules that trigger inflammation. you can also check out more blogs about 10243-15-9

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Benzothiophene – Wikipedia,
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Photochromism and fluorescence properties of 1,2-bis(2-alkyl-1- benzothiophene-3-yl)perhydrocyclopentenes

Three 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perhydrocyclopentenes with different alkyl chain lengths (methyl, ethyl, and propyl) at the reactive carbons were synthesized, and their photophysical properties were compared with those of 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perfluorocyclopentenes. The structures of the perhydrocyclopentenes were analyzed by X-ray crystallography, and their cyclization/cycloreversion reaction and fluorescence quantum yields, and fluorescence lifetimes were measured by steady-state spectroscopy and the time-correlated single photon counting method, respectively. From these results, we found the following three differences between perhydrocyclopentenes and perfluorocyclopentenes. (1) For the closed-ring isomers, the absorption bands of the perhydrocyclopentenes (around 450 nm) shifted to a shorter wavelength than those of the perfluorocyclopentenes (around 530 nm) because of the acceptor nature of the perfluorocyclopentene moiety. (2) The cyclization/cycloreversion quantum yields of the perhydrocyclopentenes were slightly larger than those of the perfluorocyclopentenes in hexane. (3) Interestingly, the fluorescence of both the open- and closed-ring isomers was observed only for the perhydrocyclopentenes, and the lifetimes of the closed-ring isomers were estimated to be <30 ps. The fluorescence of the closed-ring isomers of the perhydrocyclopentenes was mainly due to the suppression of nonradiative deactivation from the excited state directly to the ground state compared with the perfluorocyclopentenes. We¡¯ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 10243-15-9, and how the biochemistry of the body works.Synthetic Route of 10243-15-9

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Benzothiophene – Wikipedia,
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Convenient synthesis of photochromic symmetrical or unsymmetrical bis(heteroaryl)maleimides via the Suzuki-Miyaura cross-coupling reaction

A general method for the synthesis of symmetrical or unsymmetrical bis(heteroaryl)maleimides by a one-pot procedure involving Suzuki-Miyaura cross-coupling sequence was developed on the basis of the reaction of 3,4-diiodo-1-benzyl-1H-pyrrole-2,5-dione with cyclic boronate esters using PdCl2(dppf) as the catalyst. Photochromic properties of the products were examined.

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Reference of 10243-15-9, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 10243-15-9, molcular formula is C9H7BrS, introducing its new discovery.

Sterically hindered diarylethenes with a benzobis(thiadiazole) bridge: Photochemical and kinetic studies

Four rationally designed diarylethenes (DAEs) 1-4 with a benzobis(thiadiazole) bridge are specifically designed for gaining insights into steric effects on photochromic performances. It is shown that, upon increasing steric hindrance, the exchanging rate between two main conformers in the ring-open form gradually slows down, offering the opportunity for isolating photoactive anti-parallel conformers. Impressively, the separated anti-parallel conformer shows high cyclization quantum yields over the unresolved common DAEs. The typical donor-pi-acceptor (D-pi-A) feature in ring-open DAEs 1-4 endows their prominent fluorescence, which can be conveniently modulated by photocyclization. In the ring-closed form, the excess steric hindrance is found to seriously disrupt the thermal bistability, and particularly 3c fades quickly with a half-life of several hours at ambient temperature. In contrast, both 1c and 2c exhibit excellent stability, which originates from the stabilization effects of intramolecular hydrogen bonds. This work demonstrates the steric effects on the photochemical and kinetic behaviors of DAEs, providing a unique approach to develop photochromic DAEs with high photosensitivity.

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Benzothiophene – Wikipedia,
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5,6,7,12-Tetrahydrodibenz[c,f][1,5]azabismocines: Highly reactive and recoverable organo-bismuth reagents for cross-coupling reactions with Aryl Bromides

Hypervalent organobismuth compounds efficiently couple with aryl bromides in the presence of [Pd(PPh3)4] catalyst. Application of this protocol to a one-pot multi-coupling reaction with bromophenylboronic esters leads to the formation of up to nine bonds in good yields (see scheme).

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Reversible Photomodulation of Electronic Communication in a pi-Conjugated Photoswitch-Fluorophore Molecular Dyad

The extent of electronic coupling between a boron dipyrromethene (BODIPY) fluorophore and a diarylethene (DAE) photoswitch has been modulated in a covalently linked molecular dyad by irradiation with either UV or visible light. In the open isomer, both moieties can be regarded as individual chromophores, while in the closed form the lowest electronic (S0?S1) transition of the dyad is slightly shifted, enabling photomodulation of its fluorescence. Transient spectroscopy confirms that the dyad behaves dramatically different in the two switching states: while in the open isomer it resembles an undisturbed BODIPY fluorophore, in the closed isomer no fluorescence occurs and instead a red-shifted DAE behavior prevails.

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A SYNTHESIS OF BENZONAPHTHO<2,3-d>THIOPHENE DERIVATIVES via BENZOTHIOPHENE-2,3-QUINODIMETHANE INTERMEDIATES

2-Methyl- and 2-ethyl-3-(alpha-aryl)hydroxymethylbenzothiophene (6a)-(6d) were heated at 400 deg C for 5 min to yield the corresponding benzonaphtho<2,3-d>thiophene derivatives (9a)-(9d), respectively.In a similar fashion, the alcohol (8a) gave 5-methylbenzonaphtho<2,3-d>thiophene (9e) and 5,10-dimethyl derivative (3). 8-Methoxy-5-methyl- (9f) and 5-phenyl derivative (9g) were obtained from the corresponding alcohols (8b) and (8c), respectively.

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10243-15-9, Name is 3-Bromo-2-methylbenzo[b]thiophene, belongs to benzothiophene compound, is a common compound. Quality Control of 3-Bromo-2-methylbenzo[b]thiopheneIn an article, once mentioned the new application about 10243-15-9.

Synthesis and Reactions of 2,3,5,6-Tetrahydro-2,5-ethano-3-benzazocin-4(1H)-one and a Thieno-extended Analogue: X-Ray Structure of 3-Methyl-2,3,5,6-tetrahydro-2,5-ethano<1>benzothieno<3,2-d>azocin-4(1H)-one

5,6,7,8,9,10-Hexahydro-6,9-methanobenzocyclo-octen-11-one (3) was prepared through condensation of o-xylene-alpha,alpha’-diyl dibromide with N-cyclopentylidenepyrrolidine and converted by Beckmann rearrangement of its oxime (4) into 2,3,5,6-tetrahydro-2,5-ethano-3-benzazocin-4(1H)-one (6). 2,3-Bis(bromomethyl)benzothiophene was converted similarly into a mixture of 1,4,5,6-tetrahydro-2,5-ethano<1>benzothieno<2.3-d>azocin-3(2H)-one (15) and the isomeric lactam (19).Lactam (6) was N-methylated and both the parent lactam (6) and the N-methyl derivative (23) were reducedwith lithium aluminium hydride to the saturated products (24) and (25), respectively.Conversion of lactam (6) into the corresponding thiolactam (26) with phosphorus pentasulphide followed by alkylation of the latter compound gave an N-(29) or S-alkylated derivative, (27) or (28), depending on the reagent and reaction conditions.Similar reactions are reported also for lactams (15) and (19).The 4(1H)-one structures of compounds (15) – (22) are based on an X-ray analysis of 3-methyl-2,3,5,6-tetrahydro-2,5-ethano<1>benzothieno<3,2-d>azocin-4(1H)-one (20).We also report syntheses of 2-azido-5,6,7,8,9,10-hexahydro-6,9-methanobenzocyclo-octen-11-one (33) and 3-nitro(and 1,3-dinitro)-6,7,8,9,10,11-hexahydro-7,10-methanocyclo-octa<1>benzothiophen-12-one, (36) and (37), respectively.

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Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes

Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes’ intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Synthesis of a novel family of photochromic amorphous molecular materials based on dithienylethene, their photochromic properties and application for dual image formation

A novel family of photochromic amorphous molecular materials containing a dithienylethene moiety, 1-{5-[4-(di-p-tolylamino)phenyl]-2-methylthiophen-3-yl}-2- (2,5-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene, 1-{5-[4-(di-p-tolylamino)phenyl]-2-methylthiophen-3-yl}-2- (2-methylbenzo[b]thiophen-3-yl)-3, 3,4,4,5,5-hexafluorocyclopentene and 1,2-bis{5-[4-(di-p-tolylamino)phenyl]-2-methylthiophen-3-yl}-3, 3,4,4,5,5-hexafluorocyclopentene, have been designed and synthesised. These compounds, together with their photocyclised products, were found to readily form amorphous glasses with well-defined glass transition temperatures and to undergo photochromism as amorphous films as well as in solution. These compounds are characterised by high quantum yields for the photocyclisation reactions, very low quantum yields for the reverse ring-opening reactions and, hence, almost 100% fractions of the photocyclised form at the photostationary state in solution. These results suggest that the anti-parallel conformer is more populated than the parallel conformer. Optical dichroism was induced by irradiation of coloured films of the photocyclised compounds with linearly polarised red light, and dual image formation at the same location was realised by utilising this phenomenon.

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Benzothiophene – Wikipedia,
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