222730-43-0

Basic information

• Product Name: Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl-
• CAS NO: 222730-43-0
• Molecular Formula: C15H8Cl2F6S2
• Molecular Weight: 437.257
• Mol File: 222730-43-0.mol

Chemical Properties

• CAS DataBase Reference: Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl-(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl-(222730-43-0)
• EPA Substance Registry System: Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl-(222730-43-0)

Safety Data

• Hazardous Substances Data: 222730-43-0(Hazardous Substances Data)

Usage

Uses

Due to the lack of specific information on the uses of Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-methylin the provided materials, it is not possible to list its applications. However, based on the general properties of thiophene compounds, they are commonly used in various industries, such as:
Used in Pharmaceutical Industry:
Thiophene compounds are often used as building blocks for the synthesis of pharmaceuticals, agrochemicals, and other bioactive molecules due to their diverse chemical properties and potential for modification.
Used in Material Science:
Thiophene compounds can be used in the development of organic materials, such as conducting polymers and organic semiconductors, for applications in electronic devices, sensors, and energy storage systems.
Used in Chemical Synthesis:
Thiophene compounds can serve as intermediates or reagents in various chemical synthesis processes, enabling the production of a wide range of organic compounds with different functionalities and applications.

Upstream product

• 17249-82-0 2-chloro-5-methylthiophene 

Downstream Products

• 194423-31-9 3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-(4-methylphenyl)(3-thienyl))cyclopent-1-enyl)-2-methyl-5-(4-methylphenyl)thiophene 
• 154566-75-3 1,2-bis(5'-formyl-2'-methylthien-3'-yl)perfluorocyclopentene 
• 156686-76-9 1,2-Bis-<5'-(4''-methoxyphenyl)-2'-methylthien-3'-yl>perfluorocyclopentene 
• 224440-78-2 1,2-bis-[2′-methyl-5′-(4″-cyanophenyl)-3′-thienyl]perfluorocyolopentene 
• 156686-73-6 1,2-Bis-<5'-(4''-hydroxyphenyl)-2'-methylthien-3'-yl>perfluorocyclopentene 
• 348639-12-3 4,4'-(4,4'-perfluorocyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-4,2-diyl)dibenzaldehyde 
• 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 
• 1355044-13-1 1,2-bis-[5-(m-hydroxyphenyl)-2-methylthien-3-yl]hexafluorocyclopentene 
• 243971-25-7 1,2-bis(2-methyl-5-(4-carboxyphenyl)thiophen-3-yl)hexafluorocyclopentene 
• 210093-64-4 1,2-bis[2-methyl-5-(p-(hydroxymethyl)phenyl)-3-thienyl]hexafluorocyclopentene 
• 159590-16-6 3,3'-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-bromo-2-methylthiophene) 
• 676461-03-3 1,2-bis[2-methyl-5-(p-(N,N-dimethylamino)phenyl)-3-thienyl]perfluorocyclopentene 

Relevant articles and documents

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.

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.