56598-43-7

Basic information

• Product Name: 3,4-[(Thiophene-3,4-diyl)bis(thiophene-3,4-diyl)]thiophene
• Synonyms: 3,4-[(Thiophene-3,4-diyl)bis(thiophene-3,4-diyl)]thiophene;Cycloocta[1,2-c:3,4-c':5,6-c'':7,8-c''']tetrathiophene;CBPCBQMVOGRAQT-UHFFFAOYSA-N
• CAS NO: 56598-43-7
• Molecular Formula: C16H8S4
• Molecular Weight: 328.49
• Mol File: 56598-43-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-[(Thiophene-3,4-diyl)bis(thiophene-3,4-diyl)]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-[(Thiophene-3,4-diyl)bis(thiophene-3,4-diyl)]thiophene(56598-43-7)
• EPA Substance Registry System: 3,4-[(Thiophene-3,4-diyl)bis(thiophene-3,4-diyl)]thiophene(56598-43-7)

Safety Data

• Hazardous Substances Data: 56598-43-7(Hazardous Substances Data)

Upstream product

• 3141-26-2 3,4-dibromothiophene 
• 5556-13-8 4,4′-dibromo-3,3′-bithiophene 

Relevant articles and documents

Thiophene-Based Double Helices: Syntheses, X-ray Structures, and Chiroptical Properties

We demonstrate facile and efficient construction of conjugated double helical ladder oligomers from the saddle-shaped cyclooctatetrathiophene (COTh) building blocks. The key step involves deprotonation of tetra[3,4]thienylene (β,β-COTh) with n-BuLi which displays remarkably high ipsilateral selectivity. Three racemic double helical ladder oligomers, rac-DH-1, rac-DH-2, and rac-DH-3, containing two, three, and five COTh annelated moieties are efficiently synthesized by diastereoselective coupling of the racemic precursors. The X-ray crystallographic studies of rac-DH-1, rac-DH-2 and rac-DH-3 unambiguously revealed that each double helical scaffold has two single helices intertwined with each other via the C-C single bonds. Following removal of TMS groups, double helical ladder oligomer rac-DH-1-D had sufficient solubility to be resolved via chiral HPLC, thus enabling determination of its chirooptical properties such as CD spectra and optical rotation. (+)-DH-1-D has a large barrier for racemization, with lower limit of ΔG? > 48 kcal mol-1, which may be compared to DFT-computed barrier of 51 kcal mol-1. The enantiomers of DH-1-D show 1 order of magnitude stronger chirooptical properties than the carbon-sulfur [7]helicene, as determined by the anisotropy factor g = Δ?/? = -0.039, based on Δ?max = -11 and ? = 2.8 × 102 L mol-1 cm-1 in cyclohexane at 327 nm.

Synthesis of Tetrasilatetrathia[8]circulenes through C-I and C-H Silylation

We have succeeded in the synthesis of various tetrasilatetrathia[8]circulenes with alkyl and aryl groups on the silicon atoms. We also disclosed the effect of phosphine ligands on palladium-catalyzed silylation of tetraiodotetrathienylene and rhodium-cata

New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization

New synthetic methods for polycyclic thiophenes were developed. Thus, dithienothiophenes, cyclopentadithiophene, silacyclopentadithiophenes, and cyclooctatetrathiophenes were synthesized in moderate to good yields by using the CuCl2-mediated cyclization of organocopper(I) and organozinc intermediates prepared from dilithio-derivatives with CuCN or ZnCl2, respectively. A direct cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) also gave dithienothiophenes, cyclopenta-dithiophenes, and silacyclopentadithiophenes in good yields.