219537-97-0

Usage

Uses

Used in Pharmaceutical Industry:
Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[5-chloro-2-methylis used as a building block for drug discovery for its potential to be incorporated into the molecular structures of new pharmaceutical compounds. The presence of diverse functional groups allows for various chemical modifications, which can be exploited to enhance the pharmacological properties of drug candidates.
Used in Agrochemical Industry:
In the agrochemical industry, Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[5-chloro-2-methylmay be utilized as a precursor or intermediate in the synthesis of agrochemicals, such as pesticides or herbicides. Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[5-chloro-2-methyl-'s structural features could contribute to the development of novel agrochemicals with improved efficacy and selectivity.
Used in Materials Science:
Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[5-chloro-2-methylis used in materials science for the synthesis of new materials with specific properties. Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[5-chloro-2-methyl-'s heterocyclic nature and substituents may contribute to the creation of materials with unique electronic, optical, or mechanical characteristics, suitable for applications in various industries, such as electronics, energy, or nanotechnology.

Upstream product

• 17249-82-0 2-chloro-5-methylthiophene 
• 2873-74-7 gloutaric dichloride 

Downstream Products

• 391895-16-2 3-(2-(5-chloro-2-methylthiophene-3-yl)cyclopent-1-enyl)-5-phenyl-2-methylthiophene 
• 911289-22-0 1,2-bis(5'-(dimesitylboryl)-2'-methylthien-3'-yl)pentene 
• 880088-25-5 1-[5-(4-bromophenyl)-2-methylthien-3-yl]-2-(2-methyl-5-phenylthien-3-yl)cyclopentene 
• 880088-24-4 1-[5-(3-bromophenyl)-2-methylthien-3-yl]-2-(2-methyl-5-phenylthien-3-yl)cyclopentene 
• 872858-24-7 1,2-bis[5'-(4''-acetylthio)-2'-methylthien-3'-yl]cyclopentene 
• 1349697-55-7 C₄₇H₆₂N₂O₂S₂ 
• 1349697-56-8 C₄₇H₆₂N₂O₄S₂ 
• 1349697-57-9 C₅₃H₇₄N₂O₂S₂ 
• 1388152-22-4 1,2-bis(2-methyl-5-(4-methylphenyl)thien-3-yl)cyclopent-1-ene 
• 869206-30-4 4,4'-(cyclopent-1-ene-1,2-diyl)bis(N-cyclohexyl-5-methylthiophene-2-carboxamide) 
• 608528-49-0 1,2‐bis(2‐methyl‐5‐(pyridin‐4‐yl)thiophen‐3‐yl)cyclopent‐1‐ene 

Relevant academic research and scientific papers

Low-symmetry porphyrin analogues with flexible open-form dithienylethene moieties: Intense near IR Q bands

Two low-symmetry porphyrinoids with a dithienylethene (DTE) moiety incorporated into the core macrocycle, that contain either a CHO or a bridging methyl ether group, have been serendipitously synthesized through a Rothemund condensation reaction. X-ray crystal structures demonstrate that CHO and bridging methyl ether groups on the DTE moiety changes the conformation of the macrocycle and significantly influences the relative energies of the frontier orbitals of the porphyrinoid π-system and results in a remarkable enhancement and broadening of the Q bands in the 450–800 nm region compared to those of conventional tetrapyrrolic porphyrins. The introduction of a DTE moiety provides an effective strategy for achieving the intense near-infrared region absorption that is required for many of the practical applications of porphyrinoids, through a disruption of the macrocyclic π-system that is similar to that of naturally occurring corrins.

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.

Visible-light photoswitching of ligand binding mode suggests G-quadruplex DNA as a target for photopharmacology

We report the selective targeting of telomeric G4 DNA with a dithienylethene ligand and demonstrate the robust visible-light mediated switching of the G4 ligand binding mode and G-tetrad structure in physiologically-relevant conditions. The toxicity of the ligand to cervical cancer cells is modulated by the photoisomeric state of the ligand, indicating for the first time the potential of G4 to serve as a target for photopharmacological strategies.

Fluorescent molecular photoswitch based on basket-shaped porphyrins

Here we present two novel basket-shaped porphyrins bridged by photochromic diarylethene derivatives, which show significant photoswitchable fluorescent properties. Their synthesis, structures, photochromism and fluorescence characteristics were reported in detail. They are desirable for reversible light-driven fluorescent molecular switches.

Light-controlled self-assembly of a dithienylethene bolaamphiphile in water

The self-assembly of bolaamphiphiles comprised of a central photochromic dithienylethene (DTE) chromophore was investigated in aqueous media. Irradiation at 254 nm induced a conversion from the open to closed states of the DTE chromophores. Whereas, in water, irradiation produced a photostationary state of 20 : 80 (open/closed), in methanol the ratio improved to 10 : 90 (open/closed). The open → closed transition was accompanied by the formation of 1D nanofibers during incubation in darkness. This journal is

A novel approach to achieve molecular switching in solid-state driving by thermal treatment: A photochromic zinc-coordination polymer

The molecular switching of complexes based on diarylethenes in a solid-state is their most frequently studied property. This switching becomes possible when the active carbon atoms acquire a suitable interatomic separation in the molecule. Even if the structural analysis may suggest conditions disfavouring the occurrence of such switching, it may still be enabled by post-synthetic modification of the sample, like dehydration. In the present study, a novel one-dimensional coordination polymer with composition {[Zn(μ3-HA)(H2O)3]·H2O}n (I) was prepared and characterized. In its solid state, however, its thiophene rings were arranged in the non-switchable conformation yielding a C···C separation 4.148(6) ? between the active carbon atoms. After fully dehydrating the sample, this interatomic separation decreased to 3.814 ?, making it susceptible to photochromism by UV radiation.

Photostimulus-Responsive Large-Area Two-Dimensional Covalent Organic Framework Films

Using an external stimulus to modulate the electronic structure of covalent organic frameworks (COFs) is very important because such a response will endow them with additional functions. A two-dimensional (2D) COF, constructed from a photo-responsive unit (1,2-bis(5-formyl-2-methylthien-3-yl)cyclopentene), can reversibly switch its electrical conductivity 200 times from low state (the open form) to high state (the closed form) upon irradiation with UV light and reversible with visible light. This reversible phenomenon can be monitored through a circuit containing a light-emitting diode (LED). Photoinduced ring-closing/opening reactions do not destroy the integrity of the frameworks, and both processes follow logarithmic carrier generation with time. Moreover, the correlation between COFs electronic properties and changes in photoinduced kinetics and absorption curves has been demonstrated.

Photoactivation of the cytotoxic properties of platinum(II) complexes through ligand photoswitching

The development of photoactivatable metal complexes with potential anticancer properties is a topical area of current investigation. Photoactivated chemotherapy using coordination compounds is typically based on photochemical processes occurring at the metal center. In the present study, an innovative approach is applied that takes advantage of the remarkable photochemical properties of diarylethenes. Following a proof-of-concept study with two complexes, namely, C1 and C2, a series of additional platinum(II) complexes from dithienylcyclopentene-based ligands was designed and prepared. Like C1 and C2, these new coordination compounds exhibit two thermally stable, interconvertible photoisomers that display distinct properties. The photochemical behavior of ligands L3-L7 has been analyzed by 1H NMR and UV-vis spectroscopies. Subsequently, the corresponding platinum(II) complexes C3-C7 were synthesized and fully characterized, including by single-crystal X-ray diffraction for some of them. Next, the interaction of each photoisomer (i.e., containing the open or closed ligand) of the metal complexes with DNA was examined thoroughly using various techniques, revealing their distinct DNA-binding modes and affinities, as observed for the earlier compounds C1 and C2. The antiproliferative activity of the two forms of the complexes was then assessed with five cancer cell lines and compared with that of C1 and C2, which supported the use of such diarylethene-based systems for the generation of a new class of potential photochemotherapeutic metallodrugs.

Design, syntheses and photochromic properties of dithienylcyclopentene optical molecular switches

A kind of basal diarylethene through an easy synthetic procedure was synthesized and characterized, and a Suzuki coupling reaction was frequently operated to obtain the diarylethenes derivatives with some vivid functional groups like bromo, amido and pyridine. Two methods for derivatives of these switches contain porphyrins were described. All of their spectroscopic and photochromic properties were studied and intercompared. It is indicated that the difference in electron densities of the π-conjugated system of the closed forms has effects upon the absorption maxima in visible region of UV–Vis spectra. Dithienylcyclopentenes linked to porphyrins could emit luminescence substantially that display potentials to be used in the applications of nondestructive readout upon binary data storage and smart materials.

Synthesis and properties of tetraphenylethylene derivatived diarylethene with photochromism and aggregation-induced emission

A series of new diarylethene compounds with both photochromism and aggregation-induced emission have been synthesized by connecting tetraphenylethene and triphenylethene to the bisthienylethene. All the four compounds exhibit good photochromism upon irradiation with alternative UV and visible light. And they are all provided with aggregation-induced emission properties in tetrahydrofuran solution with different fraction of water, non-emissive in the pure tetrahydrofuran solution but yellowish green fluorescence in the aggregate or solid state. Furthermore, the compounds connecting tetraphenylethene to the bisthienylethene were found to exhibit the stronger fluorescence emission in the aggregate or solid state than the ones connecting triphenylethene to the bisthienylethene.