Benzo[1,2-b:4,5-b']dithiophene-4,8-dione Chemical Properties

Melting point:

260-262℃

Boiling point:

408.0±35.0 °C(Predicted)

Density 

1.595

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Amber to Dark green

InChI

InChI=1S/C10H4O2S2/c11-7-5-1-3-13-9(5)8(12)6-2-4-14-10(6)7/h1-4H

InChIKey

SIUXRPJYVQQBAF-UHFFFAOYSA-N

SMILES

C12C(=O)C3C=CSC=3C(=O)C=1C=CS2

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29349990

Benzo[1,2-b:4,5-b']dithiophene-4,8-dione Usage And Synthesis

Description

Benzo[1,2-b:4,5-b’]dithiophene is a planar symmetrical molecular structure of the thiophene derivative, enabling a better π-π?stacking and good electron delocalization that encourages charge transport. In recent years, it has been intensively studied for the application of OFETs and OPVs. The incorporation of a low-band-gap unit into the benzo[1,2-b:4,5-b’]dithiophene unit could potentially result in a red-shifted absorption due to its electron-rich properties. Benzo[1,2-b:4,5-b’]dithiophene can be chemically modified to fine-tune its chemical structure and electron properties (e.g. band gap), energy levels, and charge mobility of the small molecule/polymers of interest (at a molecular level).

Uses

BDTD can be used as an acceptor layer in the fabrication of polymer based solar cells.

Uses

suzuki reaction

General Description

Benzo[1,2-b:4,5-b′]dithiophene-4,8-dione (BDTD) is a conductive polymer with a symmetric and planar conjugated structure which has a hole mobility of 0.25 cm²V^-1s^-1.

Synthesis

The general procedure for the synthesis of benzo[1,2-B:4,5-B']dithiophene-4,8-dione from N,N-diethyl-3-thiophenecarboxamide was as follows: 6.82 g (37.25 mmol, 1.0 eq.) of N,N-diethyl-3-thiophenecarboxamide was added to a 100 mL three-necked flask protected by nitrogen and three nitrogen substitutions were performed. Subsequently 30 mL of freshly distilled tetrahydrofuran was added. The reaction mixture was cooled in an ice-salt bath until the internal temperature was reduced to 0 °C, then 15.0 mL (37.25 mmol, 1.0 eq.) of 2.5 M n-butyllithium solution was slowly added dropwise for a controlled time of 20 min. After the dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes. Subsequently, the reaction mixture was poured into 40 g of crushed ice and stirred overnight. On the following day, the product was collected by diafiltration and washed sequentially with water, methanol and petroleum ether. Finally, the resulting yellow powder was dried under vacuum to afford benzo[1,2-B:4,5-B']dithiophene-4,8-dione 3.50 g in 86.1% yield.

References

[1] Patent: CN106866700, 2017, A. Location in patent: Paragraph 0022; 0024; 0025; 0026; 0034; 0038; 0040; 0041-042
[2] Journal of Materials Chemistry A, 2014, vol. 2, # 33, p. 13580 - 13586
[3] Journal of Materials Chemistry A, 2016, vol. 4, # 47, p. 18409 - 18415
[4] Organic Electronics: physics, materials, applications, 2016, vol. 37, p. 312 - 325
[5] Chemistry - A European Journal, 2015, vol. 21, # 45, p. 16252 - 16265

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