331432-79-2

Upstream product

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

Downstream Products

• 1048658-54-3 1,2-bis[2'-methyl-5'-[(4-tert-butylphenylamino)carbonyl]-thien-3'-yl]cyclopent-1-ene 
• 1048658-44-1 1,2-bis[2'-methyl-5'-{[((R)-1-methyl-3-phenylpropyl)amino]carbonyl}thien-3'-yl]cyclopent-1-ene 
• 869206-30-4 4,4'-(cyclopent-1-ene-1,2-diyl)bis(N-cyclohexyl-5-methylthiophene-2-carboxamide) 
• 532930-47-5 1,2-bis[2'-methyl-5'-[(phenylamino)carbonyl]-thien-3'-yl]cyclopent-1-ene 
• 1048658-51-0 1,2-bis[2'-methyl-5'-[(1-cyclohexylmethylamino)carbonyl]-thien-3'-yl]cyclopent-1-ene 
• 1048658-53-2 1,2-bis[2'-methyl-5'-[(benzylamino)carbonyl]-thien-3'-yl]cyclopent-1-ene 
• 1048658-55-4 1,2-bis[2'-methyl-5'-[{3,5-di(tert-butyl)phenylamino}carbonyl]-thien-3'-yl]cyclopent-1-ene 
• 1349697-58-0 C₅₇H₆₂N₂O₆S₂ 
• 1349697-57-9 C₅₃H₇₄N₂O₂S₂ 
• 1349697-55-7 C₄₇H₆₂N₂O₂S₂ 
• 1349697-56-8 C₄₇H₆₂N₂O₄S₂ 

Relevant academic research and scientific papers

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.

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.

Acetylcholinesterase inhibitors with photoswitchable inhibition of β-amyloid aggregation

Photochromic cholinesterase inhibitors were obtained from cis-1,2-α-dithienylethene-based compounds by incorporating one or two aminopolymethylene tacrine groups. All target compounds are potent acetyl- (AChE) and butyrylcholinesterase (BChE) inhibitors in the nanomolar concentration range. Compound 11b bearing an octylene linker exhibited interactions with both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Yet upon irradiation with light, the mechanism of interaction varied from one photochromic form to another, which was investigated by kinetic studies and proved "photoswitchable". The AChE-induced β-amyloid (Aβ) aggregation assay gave further experimental support to this finding: Aβ1-40 aggregation catalyzed by the PAS of AChE might be inhibited by compound 11b in a concentration-dependent manner and seems to occur only with one photochromic form. Computational docking studies provided potential binding modes of the compound. Docking studies and molecular dynamics (MD) simulations for the ring-open and -closed form indicate a difference in binding. Although both forms can interact with the PAS, more stable interactions are observed for the ring-open form based upon stabilization of a water molecule network within the enzyme, whereas the ring-closed form lacks the required conformational flexibility for an analogous binding mode. The photoswitchable inhibitor identified might serve as valuable molecular tool to investigate the different biological properties of AChE as well as its role in pathogenesis of AD in in vitro assays.

Autoamplification of molecular chirality through the induction of supramolecular chirality

The novel concept for the autoamplification of molecular chirality, wherein the amplification proceeds through the induction of supramolecular chirality, is presented. A solution of prochiral, ring-open diarylethenes is doped with a small amount of their chiral, ring-closed counterpart. The molecules co-assemble into helical fibers through hydrogen bonding and the handedness of the fibers is biased by the chiral, ring-closed diarylethene. Photochemical ring closure of the open diarylethene yields the ring-closed product, which is enriched in the template enantiomer. There and back again: Doping a mixture of rapidly interconverting prochiral, open diarylethenes (left) with their enantiopure, closed counterparts, led to formation of gel fibers of preferred helicity (center). This supramolecular chirality was transferred to the molecular level by photochemical ring closing, thus yielding a chiral product (right) which is enriched in the enantiomer originally used as a template.