61074-71-3

Upstream product

• 17249-82-0 2-chloro-5-methylthiophene 
• 554-14-3 2-Methylthiophene 

Downstream Products

• 154566-75-3 1,2-bis(5'-formyl-2'-methylthien-3'-yl)perfluorocyclopentene 
• 159590-16-6 3,3'-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-bromo-2-methylthiophene) 
• 1263306-08-6 1-(5-formyl-2-methyl-3-thienyl)-2-(2-methyl-5-[4-ethenyl-N,N-dimethylaniline]-3-thienyl)perfluorocyclopentene 
• 1263306-00-8 1-(5-formyl-2-methyl-3-thienyl)-2-(2-methyl-5-phenylethynyl-3-thienyl)perfluorocyclopentene 
• 1263306-06-4 1-(5-chloro-2-methyl-3-thienyl)-2-(2-methyl-5-[4-ethenyl-N,N-dimethylaniline]-3-thienyl)perfluorocyclopentene 
• 1263305-98-1 1-(5-chloro-2-methyl-3-thienyl)-2-(2-methyl-5-phenylethynyl-3-thienyl)perfluorocyclopentene 

Relevant academic research and scientific papers

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.

PYRAZOLYL-BASED CARBOXAMIDES V

The invention relates to pyrazolyl-based carboxamlde compounds of formula (I) useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.

Substituent and solvent effects on the fluorescent and photochromic properties of 2-(2-pyridyl)imidazole containing diarylethene derivatives

Five diarylethene derivatives with 2-(2-pyridyl)imidazole as the ethene bridges (PI-BTEs) were synthesized and characterized. The structures and performances of the PI-BTEs (L1-L5) could be modified from not only the thiophene unit, but also the substituent on the imidazole nitrogen. Noteworthily, replacing the thiophene with the benzothiophene, the fatigue resistance is significantly improved, the centre absorption bands of the closed forms shift from 572 nm (L3) to 550 nm (L2), and the colours of the solutions change from pale pink in L3 to red-purple in L2. Additionally, the Stokes shift (Δν) values of L3 in various solvents display good linear relationships with the donor number (DN) of the solvents, and the solvent polarity parameter Δf.

A photoswitchable and thermally stable axially chiral dithienylperfluorocyclopentene dopant with high helical twisting power

A chiral dithienylperfluorocyclopentene molecule bearing two bridged binaphthyl units was designed and synthesized by a Suzuki-Miyaura cross-coupling reaction between chiral binaphthyl iodide and dithienylperfluorocyclopentene- derived bis(boronic ester). Its photoresponsive properties were investigated in both organic solvent and liquid crystal media. The UV-vis spectra exhibited typical photochromic changes of diarylethenes upon UV irradiation. The CD spectral changes upon light irradiation indicated that the conformation of binaphthyl units and the chiroptical properties of this molecule could be modulated by light. More importantly, when using as a chiral dopant in nematic liquid crystals, this molecule could induce cholesteric liquid crystals with very high helical twisting powers. At very low doping concentrations, this dopant was able to induce a reversible isothermal phase transition between nematic and cholesteric phases upon light irradiation. The photochemical control of the pitch length of cholesteric phases at higher doping concentrations enabled the reversible reflection wavelength control in the visible region. Superior thermal stability and excellent fatigue resistance were also observed during the photoswitching process, which are important properties for applications.

New fast synthesis route for symmetric and asymmetric phenyl-substituted photochromic dithienylethenes bearing functional groups such as alcohols, carboxylic acids, or amines

This Letter describes an efficient three-step synthesis route of symmetric and asymmetric phenyl-substituted photochromic 1,2-dithienylethenes bearing unprotected functional groups (i.e., alcohols, carboxylic acids or amines). These products can be easily obtained by typical Suzuki cross-coupling between photochromic dichlorides and commercial available boronic acids or pinacol esters.

Syntheses of dithienylcyclopentene optical molecular switches

Properly functionalized dithienylethenes show promise for light-induced switching processes. To prevent cis/trans isomerization from competing with conrotatory 6π-electron ring closure, the ethene segment is usually incorporated in a (perfluorinated) cyclopentene. In the present article syntheses of perhydrocyclopentene 1 and perfluorocyclopentene 2 are described, which are amenable for large-scale conversions. Both compounds have chloro substituents at the 5-position of the thiophene rings to allow further functionalization. The conversion of the chloro substituents of 1 to formyl, carboxylate, boronyl, and hydrogen groups by halogen/lithium exchange at room temperature is described, and examples are given of further elaboration of 1 and 2 by attachment, both in a symmetrical as well as unsymmetrical fashion, of additional functionality by condensation, Friedel-Crafts or Suzuki reactions. The newly prepared thienylperhydrocyclopentene derivatives show reversible photochromism if the substituents at the 5-postions allow for conjugation with the thiophene π-system. Wiley-VCH Verlag GmbH & Co KGaA, 69451 Weinheim, Germany, 2003.

A new synthetic route to symmetrical photochromic diarylperfluorocyclopentenes

Symmetrical and photochromic diarylperfluorocyclopentene has been prepared by reaction of 3-lithio-5-chloro-2-methylthiophene with the ethyl ester of hexafluoroglutaric acid, followed by ring closure via a McMurry coupling. Compound 7 is a versatile intermediate for the development of photochromic materials.