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• 135900-99-1 3-bromo-2-methyl-5-phenylthiophene 1,1-dioxide 
• 182003-69-6 3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenyl(3-thienyl))cyclopent-1-enyl)-2-methyl-5-phenylthiophene 
• 359863-62-0 1-(2-methoxy-5-phenyl-3-thienyl)-2-(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene 
• 308255-22-3 1-[2-methyl-5-phenyl-3-thienyl]heptafluorocyclopentene 
• 522600-87-9 3-(3,3,4,4,5,5-hexafluoro-2-triphenylvinyl-cyclopent-1-enyl)-2-methyl-5-phenyl-thiophene 
• 933995-28-9 1-[1,3,5-trimethyl-1-pyrazol-4-yl]-2-[2-methyl-5-phenyl-1-thien-3-yl]perfluorocyclopentene 
• 61285-28-7 3-iodo-2-methyl-5-phenylthiophene 
• 1309657-42-8 1-(2-methyl-1-naphthyl)-2-(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene 
• 1229936-89-3 (2R,3S,5R)-5-(4-amino-6-methyl-5-(2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-en-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol 
• 1229936-73-5 4,4,5,5-tetramethyl-2-(2-(2-methyl-5-phenylthiophen-3-yl)cyclopent-1-enyl)-1,3,2-dioxaborolane 
• 1607796-22-4 1-(4-methoxymethoxy-2,6-dimethylphenyl)-2-(2-methyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluorocyclopentene 

Relevant academic research and scientific papers

The role of atropisomers on the photo-reactivity and fatigue of diarylethene-based metal-organic frameworks

Photo-responsive metal-organic frameworks (MOFs) are one example of light controlled smart materials for use in advanced sensors, data storage, actuators and molecular switches. Herein we show the design, synthesis and characterization of a photo-responsi

Development of High-Performance Pyrimidine Nucleoside and Oligonucleotide Diarylethene Photoswitches

Nucleosidic and oligonucleotidic diarylethenes (DAEs) are an emerging class of photochromes with high application potential. However, their further development is hampered by the poor understanding of how the chemical structure modulates the photochromic properties. Here we synthesized 26 systematically varied deoxyuridine- and deoxycytidine-derived DAEs and analyzed reaction quantum yields, composition of the photostationary states, thermal and photochemical stability, and reversibility. This analysis identified two high-performance photoswitches with near-quantitative, fully reversible back-and-forth switching and no detectable thermal or photochemical deterioration. When incorporated into an oligonucleotide with the sequence of a promotor, the nucleotides maintained their photochromism and allowed the modulation of the transcription activity of T7 RNA polymerase with an up to 2.4-fold turn-off factor, demonstrating the potential for optochemical control of biological processes.

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.

A dual-mode visual detector for toxic hydrazine

Hydrazine (N2H4) is one of the commonly used chemical reagents in numerous industries and applications but its toxicity to humans poses a need to develop simple visual detection methods. Herein, we demonstrate a novel dual-mode system to detect and simultaneously consume hydrazine in vapour and solution by using a small photoresponsive molecule that has altered optical response (both colourimetric and fluorescent) after reacting with hydrazine. This journal is

Norbornadiene-bridged diarylethenes and their conversion into turn-off fluorescent photoswitches

We describe the synthesis and characterization of novel diarylethene photoswitches that contain a norbornadiene bridge and operate as p-type positive photochromes. One of the double bonds of norbornadiene is furthermore utilized to attach a fluoresceine tetrazine by an iEDDA cascade reaction, thereby forming a turn-off mode fluorescent photoswitch. This journal is

Mechanistic Insights into the Triplet Sensitized Photochromism of Diarylethenes

Operating photoswitchable molecules repetitively and reliably is crucial for most of their applications, in particular in (opto)electronic devices, and related to reversibility and fatigue resistance, which both critically depend on the photoisomerization mechanism defined by the substitution pattern. Two diarylethene photoswitches bearing biacetyl triplet sensitizers either at the periphery or at the core were investigated using both stationary as well as transient UV/Vis absorption spectroscopy ranging from the femtosecond to the microsecond time scale. The diarylethene with two biacetyl moieties at the periphery is switching predominantly from the triplet excited state, giving rise to an enhanced fatigue resistance. In contrast, the diarylethene bearing one diketone at the photoreactive inner carbon atom cyclizes from the singlet excited state and shows significantly higher quantum yields for both cyclization and cycloreversion.

Reversible ON/OFF switching of photoluminescence from CsPbX3 quantum dots coated with silica using photochromic diarylethene

Highly luminescent silica-coated CsPbX3 quantum dots (QDs) with good photostability were synthesized and coupled with photochromic diarylethene to modulate the QDs' photoluminescence (PL). Upon successive UV and visible light irradiation, the P

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.

Imidazole - the thiophen is fragrant heterocyclic ultra-short wavelength photochromic diaryl ethylene compound synthetic methods and application

The invention discloses a method for synthesizing an ultrashort-wavelength photochromic diarylethene compound by using imidazole-thiophene aromatic heterocycle and an application of the compound. A photochromic material can maintain good photochromic performance in a solution or film, has weaker fluorescence when the open-loop state ranges from 265 nm to 276 nm, has high fluorescence when the closed-loop state ranges from 400 nm to 550 nm, can be applied to a fluorescent photoswitch, an anti-forgery technology, a short-wavelength high-density holographic optical storage material and the like, and compared with the symmetrical thiophene or benzothiophene octafluorocyclopentene material, the material preparing cost is lower, and the application prospect is broader.

Photochromism of new unsymmetrical diarylethenes with a quinoline moiety

Three unsymmetrical diarylethenes with a 6-membered quinoline moiety were synthesized to investigate the effects of the substituents on their photochromism, and fluorescence, and the structure of one diarylethene was determined by single crystal X-ray dif