1196-81-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Ethylbenzo[b]thiophene is used as a key intermediate in the synthesis of Raloxifene, a breast cancer therapeutic. Its presence in the molecular structure of Raloxifene contributes to the drug's effectiveness in treating and preventing osteoporosis, as well as its potential role in reducing the risk of breast cancer in postmenopausal women.
Used in Organic Industry:
2-Ethylbenzo[b]thiophene is also utilized in hydrodesulfurization reactions, which are essential processes in the petroleum industry for removing sulfur-containing compounds from crude oil. Its involvement in these reactions helps in producing cleaner and more environmentally friendly fuels, thus contributing to the overall sustainability of the industry.

InChI:InChI=1/C10H10S/c1-2-9-7-8-5-3-4-6-10(8)11-9/h3-7H,2H2,1H3

Upstream product

• 95-15-8 Benzo[b]thiophene 
• 74-96-4 ethyl bromide 
• 97-94-9 triethyl borane 
• 1191415-24-3 2-(2,2-dibromovinyl)benzenethiol 
• 64-67-5 diethyl sulfate 
• 697-11-0 hexafluorocyclobut-1-ene 
• 64860-32-8 3-bromo-2-ethylbenzothiophene 
• 75-03-6 ethyl iodide 
• 107-08-4 1-iodo-propane 
• 1442-03-1 2-methylsulfanyl-benzoyl chloride 
• 113195-41-8 1-(2-methylsulfanylbenzoyl)hexylidene(triphenyl)phosphorane 
• 113195-40-7 1-(2-methylsulfanylbenzoyl)pentylidene(triphenyl)phosphorane 
• 113195-39-4 1-(2-methylsulfanylbenzoyl)butylidene(triphenyl)phosphorane 
• 113195-37-2 1-(2-methylsulfanylbenzoyl)ethylidene(triphenyl)phosphorane 

Downstream Products

• 22720-75-8 2-acetyl benzo[b]thiophene 

Relevant academic research and scientific papers

Synthesis and the optoelectronic properties of diarylethene derivatives having benzothiophene and n-alkyl thiophene units

Six new unsymmetrical diarylethenes having both benzothiophene and n-alkylthiophene units have been synthesized. The structures of diarylethenes 2a-6a were determined by single-crystal X-ray diffraction analysis. The results showed that the alkyl chain le

Photoswitchable "turn-on" Fluorescence Diarylethenes: Substituent Effects on Photochemical Properties and Electrochromism

A series of "turn-on" fluorescence diarylethenes derived from 2,3-bis(2-methylbenzo[b]thiophen-3-yl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one (1) with alkyl and acetyl substituents were synthesized. The photochemical and photophysical properties of these derivatives, including the photoreaction of crystalline 1, were thoroughly investigated to reveal substituent effects on their properties. The results indicated that alkyl substituents did not significantly affect the absorption and emission spectra of the diarylethenes. However, large absorption and emission wavelength shifts were observed for the diarylethene with an acetyl substituent due to extension of π-π conjugation. Significantly, all of the fluorescent ring-closed forms of the compounds isomerized to their ring-open forms in the presence of Cu2+ in the dark. EPR results provide clear evidence for the formation of the compound 1 radical cation intermediate that might be generated in the reaction between c-1 and Cu2+. DFT calculations found that the ground-state activation energy for ring-opening of 1.+ was approximately 9.2 kcal mol-1 lower than that of 1 without Cu2+, such that a Cu2+-catalyzed oxidative cycloreversion reaction at room temperature might be possible.

Fully Reversible Multistate Fluorescence Switching: Organogel System Consisting of Luminescent Cyanostilbene and Turn-On Diarylethene

Multicolor tunable and multistate switchable organogel is reported, which consists of a cyanostilbene organogelator showing aggregation-induced enhanced emission and a turn-on type photochromic diarylethene dye. The mixed organogel can be reversibly switched among four different states (blue-emitting gel, nonemissive sol, green-emitting gel, and green-emitting sol) modulated by a combination of orthogonal stimuli of heat and light. It is interestingly noted that this four-state switching constitutes a combinational logic circuit consisting of two stimuli inputs and three outputs. Reversible fluorescence writing, switching, erasing, and image patterning processes on this mixture gel system are demonstrated.

Syntheses and substituent effects on the properties of unsymmetrical photochromic diarylethenes bearing a benzothiophene unit

Photochromic unsymmetrical diarylethenes 1a5a that bear different electron-donating or electron-withdrawing substitutes have been synthesized, and the structures of 2a5a determined by single-crystal X-ray diffraction analysis. Substituent effects on their

Regulation of an Ambient-Light-Induced Photocyclization Pathway (Norrish–Yang Versus 6π) by Substituent Choice

Photocyclization, irrespective of whether multiple steps (e.g., Norrish–Yang cyclization) or a single concerted step (e.g., 6π photocyclization) are involved, is an intramolecular photochemical process resulting in the formation of one new single bond to afford a ring system. In particular, visible-light-induced photocyclization offers a green and sustainable route to organic cyclic compounds that are difficult to access by thermal reactions. Herein, we describe the ambient light-induced intramolecular photocyclization of a series of donor/acceptor chromophores 1 d–3 d containing two types of photoresponsive motifs, namely an electron-deficient BF2-chelated ketone fused with an electron-rich thiophene, and probe the solution-phase and solid-state photochromic performance of these compounds. The results reveal that simple variation of R substituents on the diaryl moiety allows one to control the intramolecular photocyclization mechanism with high photochemical selectivity, e.g., under ambient light, methyl-substituted 1 d and 2 d undergo reversible 6π photocyclization, whereas ethyl-substituted 3 d exclusively undergoes irreversible Norrish–Yang photocyclization. Single-crystal X-ray analysis of Norrish–Yang cyclization products reveals the formation of four pairs of conformational enantiomers differing in the dihedral angle between benzothiophene and the BF2 core, namely (±)N-3 d@68°, (±)N-3 d@-77°, (±)N-3 d@-78°, and (±)N-3 d@-102°. The UV/Vis absorption spectra of 1 d–3 d cover a broad visible-light region (380–572 nm), while DFT and TD-DFT calculations reveal that absorption in this region is dominated by the charge-transfer (CT) transition from the thiophene-centered HOMO to the LUMO of the electron-deficient π-conjugated BF2-chelated unit and the n→π* and π→π* transitions within the latter unit. The spatial separation of the HOMO and LUMO of these dyes promotes triplet-state generation and self-photosensitizes intramolecular photocyclization in the visible-light region. Three-dimensional time-resolved and steady-state emission spectra of 3 d show that the Norrish–Yang photocyclization takes place within milliseconds with excellent conversion efficiency (96 %).

Mono-and bithiophene-substituted diarylethene photoswitches with emissive open or closed forms

We present a new series of photochromic 1,2-bis(2-ethylbenzo[b]thiophen-3-yl)perfluorocyclopentenes with an oxidized benzothiophene core (O) or a nonoxidized one, decorated with mono-(Th1) and bithiophene (Th2) units attached to positions 6 and 6′ (Sy = symmetric) or only to position 6 (As = asymmetric). Oxidized compounds have highly fluorescent closed forms emitting in the visible region (yellow to red). The dyes with nonoxidized benzothiophenes possess fluorescent open forms with rather low emission efficiency. The photoswitching kinetics was studied at several wavelengths with UV and visible light. New diarylethenes underwent ring-closure reactions by irradiation with UV light (365 nm, 405 nm), and the reversible ring-opening by irradiation with visible light (470 nm, 530 nm). The on-switching of fluorescence due to the ring-closure reaction was observed also with visible light of 470 nm (to an extent of 10% for compound SyOTh1) and attributed to the Urbach tail effect. Due to a high degree of fluorescence modulation (>270), good fatigue resistance and large fluorescence quantum yield, compound SyOTh1 emerged as a candidate for single-molecule based super-resolution fluorescence microscopy.

Photochromic diaryl ethylene compound with up-conversion luminescence property and application thereof

The invention provides a photochromic diaryl ethylene compound with up-conversion luminescence performance and application thereof. The photochromic diaryl ethylene compound has a structure as shown in a formula I in the specification. The photochromic diaryl ethylene compound is a switching type single-photon absorption up-conversion luminescent material, can realize up-conversion luminescence of high-vibration energy level absorption, and can realize the switching effect of up-conversion luminescence through regulation and control of light with multiple wavelengths. Due to the fact that light with a long wavelength has a high tissue penetrating power, the photochromic diaryl ethylene compound can also effectively eliminate background noise such as auto-fluorescence, and is expected to be applied to a super-resolution single-photon imaging system.

Fluorescence opening type diarylethene fluorescent probe, and preparation method and application thereof

The invention provides a fluorescence opening type diarylethene fluorescent probe, and a preparation method and application thereof. The fluorescence opening type diarylethene fluorescent probe has a structure as shown in a formula I, the probe is compose

Development of Red-Shifted and Fluorogenic Nucleoside and Oligonucleotide Diarylethene Photoswitches

The reversible modulation of fluorescence signals by light is of high interest for applications in super-resolution microscopy, especially on the DNA level. In this article we describe the systematic variation of the core structure in nucleoside-based diarylethenes (DAEs), in order to generate intrinsically fluorescent photochromes. The introduction of aromatic bridging units resulted in a bathochromic shift of the visible absorption maximum of the closed-ring form, but caused reduced thermal stability and switching efficiency. The replacement of the thiophene aryl unit by thiazol improved the thermal stability, whereas the introduction of a benzothiophene unit led to inherent and modulatable turn-off fluorescence. This feature was further optimized by introducing a fluorescent indole nucleobase into the DAE core, resulting in an effective photoswitch with a fluorescence quantum yield of 0.0166 and a fluorescence turn-off factor of 3.2. The site-specific incorporation into an oligonucleotide resulted in fluorescence-switchable DNA with high cyclization quantum yields and switching efficiency, which may facilitate future applications.

Di(benzothienyl)cyclobutenes: Toward Strained Photoswitchable Fluorophores

Bis(benzothienyl)ethene sulfones are very interesting molecules for super-resolution microscopy due to their photoswitching properties. However, functionalization of the ‘classical’ bis(benzothienyl)ethene sulfones with a five-membered central ring leads to significant decrease of quantum yields of photoconversion of the fluorescent closed form of the dye to the non-fluorescent open form that limits their application in microscopy. Here, we designed and synthesized diarylethenes with a fluorinated four-membered central ring that adds extra strain to the closed form of the dye. The reaction mechanism of their formation was studied, and byproducts formed upon structural rearrangement of the benzothiophene fragment were characterized. The photochromic properties of the new molecules were investigated by NMR and absorption spectroscopy. Some of these compounds show enhanced tendency to ring opening and have quantum yields of the ring-opening reaction in the range of 0.2–0.5.