17249-82-0

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-5-methylthiophene is used as a key intermediate in the synthesis of dithienylcyclopentene optical molecular switches. These switches are important components in the development of advanced materials with potential applications in optoelectronics and molecular devices.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-5-methylthiophene is utilized as an active pharmaceutical intermediate. It plays a crucial role in the development of new drugs and therapeutic agents, contributing to the advancement of medical treatments and healthcare solutions.

InChI:InChI=1/C5H5ClS/c1-4-2-3-5(6)7-4/h2-3H,1H3

Upstream product

• 554-14-3 2-Methylthiophene 
• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 

Downstream Products

• 1209480-76-1 2-[2,6-bis(5-methyl-2-thienyl)phenyl]pyridine 
• 219537-95-8 1,5‐bis(5‐chloro‐2‐methylthiophen‐3‐yl)pentane‐1,5‐dione 
• 608528-49-0 1,2‐bis(2‐methyl‐5‐(pyridin‐4‐yl)thiophen‐3‐yl)cyclopent‐1‐ene 
• 1613317-63-7 (2R,2'R)-diethyl 3,3'-((4,4'-(cyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2,2'-carbonyl))-bis(sulfanediyl))bis(2-acetamidopropanoate) 
• 869206-30-4 4,4'-(cyclopent-1-ene-1,2-diyl)bis(N-cyclohexyl-5-methylthiophene-2-carboxamide) 

Relevant academic research and scientific papers

Core-modified rubyrins containing dithienylethene moieties

Two stable core-modified rubyrins bearing one and two dithienylethene (DTE) units (1 and 2) have been synthesized. With one "closed-form" DTE unit, 1 shows aromaticity associated with its conjugated circuit of 26 π-electrons. In contrast, rubyrin 2 containing one "open-form" DTE unit has nonaromatic properties.

A new class of photochromic 1,2-diarylethenes; synthesis and switching properties of bis(3-thienyl)cyclopentenes

A novel synthetic route to diarylethenes fixed in a cyclopentene based on titanium-mediated carbonyl coupling leads to bis(3-thienyl)cyclopentenes that show photochromic behaviour similar to that of known diarylethenes.

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.

Reversible light-directed red, green, and blue reflection with thermal stability enabled by a self-organized helical superstructure

Adding external, remote, and dynamic control to self-organized superstructures with desired properties is an important leap necessary in leveraging the fascinating molecular subsystems for employment in applications. Here two novel light-driven dithienylethene chiral molecular switches possessing remarkable changes in helical twisting power during photoisomerization as well as very high helical twisting powers were found to experience photochemically reversible isomerization with thermal stability in both isotropic organic solvents and anisotropic liquid crystal media. When doped into a commercially available achiral liquid crystal host, the chiral switch was able to either immediately induce an optically tunable helical superstructure or retain an achiral photoresponsive liquid crystal phase whose helical superstructure was induced and tuned reversibly upon light irradiation. Moreover, reversible light-directed red, green, and blue reflection colors with thermal stability in a single thin film were demonstrated.

Synthesis, properties, and electrochemistry of a photochromic compound based on dithienylethene and ProDOT

The synthesis, photochromic features, and electrochemistry of a novel material based on dithienylethene (DTE) and 3,3-didecyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (didecyl-ProDOT) units are described. It is noteworthy that 1,2-bis(5-(3,3-didecyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-6-yl)-2-methylthiophen-3-yl)cyclopent-1-ene can be effciently switched between open and closed states by light in both solution and in the solid poly(methyl metacrylate) (PMMA) matrix. It is also found that the emission of this novel compound can be switched on and off upon irradiation.

Switching the Photochromic Activity of Acenaphthylene Derivatives through a Tandem Nucleophile-Promoted Addition Reaction

New acenaphthylene-based dithienylethenes have been prepared. Surprisingly they did not show photochromism. However, they readily underwent a tandem addition of a nucleophile and an electrophile, leading to a small library of dearomatized colourless analogues, which, on the contrary, were endowed with photochromic activity. In the absence of the electrophile, the intermediate obtained by C-attack readily aromatizes to give, surprisingly, a final product of direct aromatic nucleophilic substitution, which was not photochromically active.

Controlling covalent connection and disconnection with light

The on-going need for feature miniaturization and the growing complexity of structures for use in nanotechnology demand the precise and controlled formation of covalent bonds at the molecular level. Such control requires the use of external stimuli that offer outstanding spatial, temporal, as well as energetic resolution. Thus, photoaddressable switches are excellent candidates for creating a system that allows reversible photocontrol over covalent chemical connection and disconnection. Here we show that the formation of covalent bonds between two reagents and their scission in the resulting product can be controlled exclusively by illumination with differently colored light. A furyl-substituted photoswitchable diarylethene was shown to undergo a reversible Diels-Alder reaction with maleimide to afford the corresponding Diels-Alder adduct. Our system is potentially applicable in any field already relying on the benefits of reversible Diels-Alder reactions.

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.

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

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.