250-65-7

Usage

Synthesis Reference(s)

Synthetic Communications, 20, p. 2275, 1990 DOI: 10.1080/00397919008053169

Upstream product

• 1451-95-2 thiophene-2,3-dicarboxylic acid 
• 13250-85-6 2,3-bis(hydroxymethyl)thiophene 
• 13250-86-7 2,3-bis(bromomethyl)thiophene 
• 527-72-0 2-thiophenylcarboxylic acid 
• 7712-08-5 4,6-Dihydrothieno<3,4-b>thiophene 
• 1262420-60-9 2,3-dihydro-thieno[3,4-b]thiophene 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 198489-78-0 [(Z)-1-Bromo-2-(4-bromo-thiophen-3-yl)-vinyl]-trimethyl-silane 
• 198489-56-4 trimethyl-(thieno[3,4-b]thiophen-2-yl)silane 
• 131390-83-5 3-bromo-4-(trimethylsilyl)eth-1-yn-1-yl-thiophene 

Relevant academic research and scientific papers

Tuning the band gap of low-band-gap polyselenophenes and polythiophenes: The effect of the heteroatom

A series of new low-band-gap thieno-or selenolo-fused polyselenophenes (P5 and P6) and selenolo-fused polythiophene (P4) (as well as previously reported thieno-fused polythiophene, P3) was prepared systematically by electropolymerization (P4-P6) and by solid-state polymerization (P3, P5 and P6). The 2,5-dibrominated monomers (3Br2, 5Br2, and 6Br 2) undergo solid-state polymerization under slight heating and produce insoluble P3, P5, and P6 as black conducting powders. The spectroelectrochemically measured optical band gaps of P4-P6 films are 0.96, 0.72, and 0.76 eV, respectively. DFT calculations performed on P3-P6 provide excellent estimations of the experimental band gaps of these polymers. The band gap of the polyselenophenes (P5 and P6) is 0.2 eV lower than that of the corresponding polythiophenes (P3 and P4). We introduced a new scheme for band gap control in conjugated polymers by replacing the sulfur atom with a selenium atom in the main and/or peripheral ring, which leads to significant and predictable changes in the band gap of the polymers. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring. Thus, we have achieved band gap control in very low band gap (～0.7-1.0 eV) polymers through the use of different combinations of selenium and sulfur atoms in the main and peripheral rings.

Synthesis of thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds and their derivatives and use thereof

Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

Versatile synthesis of 3,4-b diheteropentalenes

We describe a new route for the synthesis of thieno[3,4-b]thiophene, alkyl derivatives thereof, seleno[3,4-b]thiophene, and thieno[3,4-b]furan made from inexpensive starting materials, such as thiophene-2-carboxylic acid and furan-2-carboxylic acid. Such fused heterocycles are of great interest for low band gap organic semiconductors and applications including OLEDs, organic photovoltaic cells, and electrochromics.

SYNTHESIS OF THIENO[3,4-b]THIOPHENE, THIENO[3,4-b]FURAN, RELATED COMPOUNDS AND THEIR DERIVATIVES AND USE THEREOF

Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

Syntheses of novel group 15 and 16 thieno[2,3-b]-, thieno[3,4-b]-, and thieno [3,2-b]-heteroles

Group 15 (P, As and Sb) and group 16 (S, Se, and Te) thieno[2,3-b]- (1), thieno[3,4-b]- (2), and thieno[3,2-b]heteroles (3) were prepared from the corresponding 1,4-dilithium intermediates, derived from (Z)-(β-bromo-β-trimethylsilylvinyl)thiophenes (6), (10), and (13) by treatment with tert-butyllithium, respectively. These thienoheteroles obtained are novel fused heterocyclicring systems, except for thienothiophenes and thienoselenophenes.

An Alternative Synthesis of Thienothiophene

Thienothiophene has been obtained in greater than 50percent yield starting from 3,4-dibromothiophene by a sequence of Pd(II)-Cu(I)-catalysed cross-coupling with trimethylsilylacetylene, bromine-lithium exchange, thiolation with elemental sulfur and ring-closure in aqueous medium.