154566-75-3

Usage

Uses

Used in Organic Synthesis:
2-Thiophenecarboxaldehyde, 4,4'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-methylis used as a reactive intermediate in organic synthesis for the preparation of various complex organic molecules. Its reactivity, stemming from the aldehyde group and the electron-withdrawing fluorine atoms, allows for a wide range of chemical reactions, such as condensation, reduction, and oxidation, enabling the synthesis of diverse organic compounds.
Used in Chemical Research:
In the field of chemical research, 2-Thiophenecarboxaldehyde, 4,4'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-methylserves as a valuable compound for studying the effects of structural modifications on the reactivity and properties of organic molecules. Its unique structure, which includes a thiophene ring, a carboxaldehyde functional group, and a hexafluoro-cyclopentene moiety, provides a platform for investigating the influence of these structural elements on the compound's reactivity and potential applications.
Used in Material Science:
2-Thiophenecarboxaldehyde, 4,4'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-methylmay have potential applications in material science due to its unique structure and properties. The presence of the thiophene ring, carboxaldehyde functional group, and hexafluoro-cyclopentene moiety could contribute to the development of new materials with specific properties, such as electrical conductivity, thermal stability, or chemical resistance. Further research and development in this area could lead to the discovery of novel materials with a wide range of applications in various industries.

Upstream product

• 154586-93-3 C₂₁H₂₂F₆O₄S₂ 
• 17249-82-0 2-chloro-5-methylthiophene 
• 61074-71-3 3-bromo-5-chloro-2-methylthiophene 
• 13679-70-4 5-methylthiophene-2-carboxaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 222730-43-0 1,2-bis(5-chloro-2-methylthien-3-yl)perfluorocyclopent-1-ene 
• 4885-02-3 Dichloromethyl methyl ether 
• 159590-08-6 3,3’-(perfluorocyclopent-1-ene-1,2-diyl)bis(2-methylthiophene) 
• 559-40-0 octaperfluorocyclopentene 
• 1195623-96-1 5-methyl-4-bromo-2-thiopheneformaldehyde diethyl acetal 
• 29421-73-6 3,5-dibromo-2-methylthiophene 
• 479196-49-1 3-bromo-5-[(1,3-dioxolane)-2-yl]-2-methylthiophene 
• 706-79-6 1,2-dichloro-3,3,4,4,5,5-hexafluorocyclopentene 
• 1314941-28-0 (5-formyl-2-methylthienyl)-3-boronic acid pinacol ester 

Downstream Products

• 154566-78-6 1-<5'-(1'',3''-Benzodithiole-2''-ylidenylmethyl)-2'-methylthien-3'-yl>-2-<5'''-formyl-2'''-methylthien-3'''-yl>perfluorocyclopentene 
• 154566-76-4 1,2-Bis<5'-(1'',3''-benzodithiole-2''-ylidenylmethyl)-2'-methylthien-3'-yl>perfluorocyclopentene 
• 384330-49-8 1,2-bis(2'-methyl-5'-(carboxylic acid)-3'-thienyl) perfluorocyclopentene 
• 1264251-34-4 1,2-bis[5-(2,2-dibromoethenyl)-2-methylthiophen-3-yl]hexafluorocyclopent-1-ene 
• 1306591-73-0 (5E,5'E)-5,5'-[(3,3,4,4,5,5-hexafluorocyclopent-1-ene-1,2-diyl)-4,4'-bis(5-methylthiophen-2-ylmethylidene)]bis(2-thioxo-1,3-thiazolidin-4-one) 
• 1306591-74-1 (5E,5'E)-5,5'-[(3,3,4,4,5,5-hexafluorocyclopent-1-ene-1,2-diyl)-4,4'-bis(5-methylthiophen-2-ylmethylidene)]bis(3-methyl-2-thioxo-1,3-thiazolidin-4-one) 
• 1306591-75-2 (5E,5'E)-5,5'-[(3,3,4,4,5,5-hexafluorocyclopent-1-ene-1,2-diyl)-4,4'-bis(5-methylthiophen-2-ylmethylidene)]bis(3-phenyl-2-thioxo-1,3-thiazolidin-4-one) 
• 1347647-88-4 C₂₅H₂₂F₆O₄S₂ 
• 1338348-36-9 C₄₉H₃₈F₆N₄S₂ 
• 1338348-37-0 C₄₉H₃₈F₆N₄O₄S₂ 
• 1338348-34-7 C₄₅H₃₀F₆N₄S₂ 
• 1400758-38-4 C₂₇H₁₇F₆NO₂S₂ 

Relevant academic research and scientific papers

Ring-opening and -closure reaction dynamics of a photochromic dithienylethene derivative

The influence of a bulky, strongly coupled substituent (benzoyl-phenyl-ethenyl, BPE) on the dynamics of the photoinduced ring-closure and ring-opening reactions of 1,2-bis[[2-methyl-thien-3-yl]]perfluorocyclopentene (BMTFP) in solution was investigated. UV/vis absorption spectroscopy in combination with chemical actinometry was employed to determine the reaction quantum yields. The relaxation and reaction dynamics were studied by transient absorption spectroscopy, exciting the S0-S2 transition of the open isomer with pump pulses at 288 nm, while 657 and 410 nm pulses were used to excite the S1 and S2 states of the closed isomer, respectively. Transient absorption spectra in the range of 350-950 nm were recorded using temporally delayed, white-light continuum probe pulses. After structural relaxation in the S1 excited state, the ring-closure reaction takes place with high quantum yield through a conical intersection. This conical intersection acts also as relaxation funnel for the S1 excited state of the closed isomer, from which it is separated by an energy barrier. The branching in the conical intersection favors the closed isomer, so that the ring-opening reaction yield is small (10-3-10-4). This yield was found to vary by a factor of 6 for different isomers obtained by rotation around the ethylene bond of the substituent.

Diarylethene-based conjugated polymer networks for ultrafast photochromic films

Diarylethene polymers are an emerging class of photochromic materials which offer new opportunities for the development of optical data recording and storage. This work reports two diarylethene-based conjugated polymer networks DPP-1 and DPP-2 constructed by Schiff-base polymerization of two-connected photochromic unit 1,2-bis(5-formyl-2-methylthiophen-3-yl)perfluorocyclopentene (DEA-CHO) and tetrahedral four-connected unit tetra(p-aminophenyl)methane (TAPM) or plane three-connected unit 1,3,5-tris(4-aminophenyl)triazine (TAPT). The molecular structures of DPP-1 and DPP-2 were characterized by FT-IR and 13C CP-MAS solid state NMR spectroscopy, and the morphology was investigated through scanning electron microscopy (SEM) and transmission electron microscopy (TEM). The model compound was used to indicate the possibility of constructing DPP-1 and DPP-2. DPP-1 and DPP-2 exhibited high chemical stability in the presence of strong acid (6 M HCl) and strong base (6 M NaOH) for 5 days. DPP-1 and DPP-2 showed ultrafast photochromic transformation between the open form (yellow) and closed form (green) with alternate irradiation of ultraviolet and visible light in 50 seconds, which were measured through UV-vis-NIR experiments. X-ray photoelectron spectroscopy (XPS) demonstrated that the electronic arrangement around the sulfur atoms changed during the process of the open form to the closed form. Moreover, DPP-1 and DPP-2 displayed excellent fatigue resistance that the absorbance only lost ca. 5% after three cycles. DPP-1/PMMA and DPP-2/PMMA films fabricated by dispersing diarylethene-based conjugated polymer networks in the poly(methyl methacrylate) (PMMA) matrix also exhibited great photochromic reversibility and fatigue resistance, which provide potential applications towards the development of optical rewritable patterning and information storage devices.

Near-infrared photochromic diarylethenes based on the changes in the π-conjugated system and the electronic properties of the heteroaryl moieties

It is very challenging to construct photochromic materials with absorption and reactivity in the near-infrared (NIR) spectral region. Herein, four unsymmetrical diarylethene derivatives 1o-4o, which contain both indole and thiophene moieties, have been successfully synthesized, and their photochromic behaviors have been shifted to the NIR region. These newly developed NIR photochromic materials are highly sensitive and responsive to photostimuli both in solution and in poly(methyl methacrylate) films. It has been shown that 1o-4o exhibit remarkable UV/Vis and fluorescence spectral changes, allowing them to behave as reversible optical molecular switches in the NIR region. Four unsymmetrical diarylethene derivatives, 1o-4o, which contain both indole and thiophene moieties, have been successfully synthesized, and their photochromic behaviors have been shifted to the NIR region. The photophysical and photochromic properties of 1o-4o were comprehensively investigated by NMR, UV/Vis, fluorescence spectral and X-ray crystallographic analysis. Copyright

Preparation method of near-infrared absorption amphiphilic diene photochromic molecule and reversible photo-thermal method Application of photoacoustic

The invention discloses preparation of a near-infrared absorption amphiphilic diene photochromic molecule and application of reversible photo-thermal and photoacoustic, and belongs to the technical field of functional materials. The structure is as follows. or. In-flight R1 , R2 , R3 Are all selected from C1 - C6 A straight-chain alkyl group. The photochromic protein nanoparticles assembled with albumin can be used for preparing photothermal therapeutic materials and photoacoustic contrast agents.

Stabilization of ultra-small gold nanoparticles in a photochromic organic cage: modulating photocatalytic CO2reduction by tuning light irradiation

Synthesis and stabilization of ultra-small metal nanoparticles (MNPs) composed of a few atoms are of paramount importance in modulating their material properties based on quantum confinement effects. The highly reactive surface of small MNPs tends to aggregate, resulting in bigger particles and subsequent deterioration of the catalytic activity. In this work, we exploited a dithienylethene (DTE) based photochromic organic cage (TAE-DTE) for thein situstabilization of ultra-small Au NPs (Au@TAE-DTE) (2reduction to CO. Importantly, irradiating with light of the full range (λ= 250-750 nm) allowed for co-existence of both photoisomers which thereby showed wide spectrum absorption as compared to individual photoisomers, consequently displaying substantially enhanced performance for the photocatalytic CO2reduction. Further, the real-time progress of the CO2reduction reaction and corresponding reaction intermediates was detected by anin situDRIFT experiment.

Diarylethene compound, preparation and applications thereof

The invention relates to a diarylethene compound, preparation and applications thereof, and specificallydiscloses a compound represented by a formula (A), wherein various groups are defined in the specification. According to the invention, the compound is an excellent photochromic compound, and can be subjected to a photoisomerization reaction under the irradiation of light with specific wavelength to generate a ring-closing compound; and the compound and the photoisomerized ring-closing derivative thereof have high activity on agricultural and forestry pests such as aphids, aedes albopictus larvae of NematoceraCulicidae, and the like, and the activity of the ring-closing compound after illumination is higher than the activity of the ring-opening compound before illumination.

Photoswitchable J-aggregated processable organogel by integrating a photochromic acceptor

A novel αchromophoric 1,4-bis(anthracenylethynyl)benzene (BAB)-based highly emissive J-aggregated organogel has been synthesized and characterized. Single-crystal structure determination of asymmetric π-chromophoric bola-amphiphilic BAB1 (dodecyl and triethyleneglycolmonomethylether containing side chains of bis(anthracenylethynyl)benzene) supports J-aggregation. Further, a photochromic acceptor chromophore, 4,4′-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2-carbaldehyde), is noncovalently encapsulated in the gel and photoswitching studies have been performed based on photochromic F?rster resonance energy transfer. The modulated emission of the processable soft material is further exploited for rewritable display. However, BAB2 (dodecyl side chain on both sides) does not show gelation property due to its low solubility.

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.

Diarylethene type photochromic insecticidal compound and preparation method and purpose thereof

The invention relates to a diarylethene type photochromic insecticidal compound and a preparation method and a purpose thereof. Specifically, the invention discloses a compound as shown in formula (A) or an optical isomer or a cis-trans-isomer thereof, or an agricultural pharmaceutically acceptable salt, and the definitions of substituent groups are as stated in the description. The invention also discloses the preparation method and the purpose of the compound. The formula (A) is shown in the description.

Photochromic thiopheneglyoxylic luen cholic acid water-soluble symmetrical entire fluorine link pentene compound, preparation method and application

The invention discloses a photochromic thiophene-linked cholic acid water-soluble symmetrical perfluorocyclopentene compound and a preparation method and application of the compound. The photochromic material can keep good photochromic property in a solution or a thin film and has fluorescence in the range of 350-550nm in an open-loop state; and furthermore, as the ultraviolet irradiation time is prolonged, the strength of a fluorescence emission spectrum is reduced. Thus, the photochromic material can be used for fluorescence detection and fluorescence light control switching; and compared with a symmetrical thiophene or benzothiophene type perfluorocyclopentene material, the compound has the advantages that the cost of the preparation materials is relatively low and the application prospects are relatively great.