473463-85-3

Basic information

• Product Name: Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[2-methyl-5-phenyl-
• CAS NO: 473463-85-3
• Molecular Formula: C27H24S2
• Molecular Weight: 412.62
• Mol File: 473463-85-3.mol

Chemical Properties

• CAS DataBase Reference: Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[2-methyl-5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[2-methyl-5-phenyl-(473463-85-3)
• EPA Substance Registry System: Thiophene, 3,3'-(1-cyclopentene-1,2-diyl)bis[2-methyl-5-phenyl-(473463-85-3)

Safety Data

• Hazardous Substances Data: 473463-85-3(Hazardous Substances Data)

Upstream product

• 391895-16-2 3-(2-(5-chloro-2-methylthiophene-3-yl)cyclopent-1-enyl)-5-phenyl-2-methylthiophene 
• 108-86-1 bromobenzene 
• 509083-61-8 1,2-bis[5'-di-n-butoxyboryl-2'-methylthien-3'-yl]cyclopentene 

Downstream Products

• 1180000-21-8 C₅₀H₆₆S₂ 
• 915951-92-7 3,4-bis(2-phenyl-5-methylthien-3-yl)-6,6-pentamethylenefulvene 

Relevant articles and documents

Photochromic properties of perhydro- and perfluorodithienylcyclopentene molecular switches

Various substituted phenylthienyl perhydro- and perfluorocyclopentenes have been synthesized in order to compare their spectroscopic and photochromic properties. The difference in the electron densities of the central cyclopentene moieties in the perhydrocyclopentene and perfluorocyclopentene molecular switches has only a small effect on the absorption maxima of the electronic spectra, but causes some subtle changes in substituent and solvatochromic effects. The photochromic behaviour is remarkably similar, and both type of switches combine excellent quantum yields (0.6) with high degrees of photoconversion (> 0.85). The main difference is the lower photochemical and thermal stability of the perhydrocyclopentene molecular switches. It is concluded that in most studies the perhydrocyclopentenes are an excellent alternative for the perfluorocyclopentenes, while the perfluorocyclopentenes might be better suited for applications such as data storage, which depend critically on fatigue resistance and thermal stability. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

An optical and theoretical investigation of the ultrafast dynamics of a bisthienylethene-based photochromic switch

The switching behavior of 1,2-bis(5-phenyl-2-methylthien-3-yl)cyclopentene is studied by means of polarization selective nonlinear optical spectroscopy and time-dependent density functional theory. The combined information from the observed population and orientational dynamics together with the results of theoretical calculations show that on a subpicosecond time scale rapid mixing and relaxation of electronic states occur, before switching takes place. Such preswitching dynamics was not studied in detail in these systems before. Then, the switching process itself occurs by the formation of a C-C bond in the central cyclopentene ring with a time constant of 4.2 ps. Driven by the ring closure, the side groups of the switch molecules rotate to a nearly coplanar conformation with a time constant of about 8 ps. The switching process is completed by relaxation of the vibrationally hot ground state of the closed form of the molecule to thermal equilibrium.

Functionalisation of MoS22D layers with diarylethene molecules

Functionalisation of two-dimensional (2D) materials with stimuli-responsive molecules has been scarcely investigated. Here, MoS2 layers obtained by chemical exfoliation are covalently and non-covalently functionalised using two photoswitchable diarylethen

Photochromic polymers bearing various diarylethene chromophores as the pendant: Synthesis, optical properties, and multicolor photochromism

Photochromic polymers with various diarylethene derivatives were synthesized by a conventional radical polymerization of styrene derivatives having diarylethene chromophores as the pendant. All the polymers exhibited reversible photochromism in the film a

Remote-control photoswitching using NIR light

(Chemical Equation Presented) Near-infrared (NIR) light is used to toggle photoswitches back and forth between their two isomers even though the chromophores do not significantly absorb this type of light. The reactions are achieved through a "remote control" process by using photon up-converting hexagonal NaYF4 nanocrystals doped with lanthanide ions. These nanoparticles absorb 980 nm light and convert it to wavelengths that can be used to trigger the photoswitches offering a practical means to potentially achieve 3D-data storage, drug-delivery, and photolithography.

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.