862681-10-5

Basic information

• Product Name: 5-(tributyltin)-2,2′-bis(3,4-ethylenedioxy)thiophene
• Synonyms: 5-(tributyltin)-2,2′-bis(3,4-ethylenedioxy)thiophene
• CAS NO: 862681-10-5
• Molecular Weight: 571.389
• Mol File: 862681-10-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-(tributyltin)-2,2′-bis(3,4-ethylenedioxy)thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(tributyltin)-2,2′-bis(3,4-ethylenedioxy)thiophene(862681-10-5)
• EPA Substance Registry System: 5-(tributyltin)-2,2′-bis(3,4-ethylenedioxy)thiophene(862681-10-5)

Safety Data

• Hazardous Substances Data: 862681-10-5(Hazardous Substances Data)

Upstream product

• 1461-22-9 tributyltin chloride 
• 195602-17-6 2,2'-bis(3,4-ethylenedioxythiophene) 

Downstream Products

• 1257983-55-3 3,3',5,5'-tetrakis[3,4,3',4'-bis(ethylenedioxy)-2,2'-bithiophen-5-yl]-2,2'-bithiophene 
• 195602-17-6 2,2'-bis(3,4-ethylenedioxythiophene) 
• 1257983-56-4 C₆₄H₄₂O₁₆S₁₂ 
• 1350319-86-6 C₄₈H₅₁NO₈S₃ 

Relevant articles and documents

Synthesis and characterization of low bandgap π-conjugated copolymers incorporating 4,7-bis(3,3′/4,4′-hexylthiophene-2-yl)benzo[c][2,1,3] thiadiazole units for photovoltaic application

4,7-Bis(3,3′/4,4′-hexylthiophene-2-yl)benzo[c][2,1,3] thiadiazoles (HT-BT-HT) were used as building blocks to construct a series of low bandgap π-conjugated copolymers for photovoltaic applications. The desired copolymers were obtained by incorporating the HT-BT-HT comonomers together with donor or acceptor units, such as 3,4-ethylenedioxythiophene (EDOT), bis-EDOT, thieno[3,4-b]pyrazine (TP), and 2,3-dimethyl-TP, via a palladium-catalyzed Stille cross-coupling method. A facile synthetic method has also been developed for the synthesis of several EDOT- and TP-based copolymers via direct C-H arylation of EDOT, bis-EDOT, and TP derivatives using the commercially available catalyst Pd(OAc)2 under Heck-type experimental conditions (Jeffery method). For all of the synthesized copolymers, moving the hexyl side chains of the HT unit in the HT-BT-HT comonomers from 3,3′-positions (close to BT, as in P1-P4) to 4,4′-positions (away from BT, as in P5-P8) led to a significant red shift of the UV-vis absorption spectrum, a decrease of the energy bandgap, an increase of the glass transition temperature, and more promising photovoltaic performances. The thin-film copolymer P7 incorporating TP units (-TP-HT-BT-HT-)n exhibited the most extended absorption (beyond 1000 nm) and the lowest optical bandgap (1.24 eV) among the synthesized copolymers. According to time-dependent density functional theory calculations, the TP unit, in contrast to EDOT, has its lowest unoccupied molecular orbital (LUMO) at the same level as BT. An extended π-conjugation along the TP and BT units leads to low-lying LUMO levels of the resulting copolymer P7 and in turn its reduced bandgap. The power conversion efficiencies (PCEs) of organic photovoltaic devices employing copolymers P1-P8 were measured in the configuration of ITO/PEDOT:PSS/copolymer (P1-P8):PC 60BM (1:1 w/w)/Al. Copolymer P7 in particular showed the highest PCE of 3.32%.