Dibenzotetrathiafulvalene Property

Melting point:

239-243 °C

Boiling point:

367.1±42.0 °C(Predicted)

Density 

1.538±0.06 g/cm3(Predicted)

Safety

Hazard Codes 

N

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P501Dispose of contents/container to..…

Dibenzotetrathiafulvalene Chemical Properties,Usage,Production

Uses

Dibenzotetrathiafulvalene(DBTTF, also known as 1,3-Benzodithiole,2-(1,3-benzodithiol-2-ylidene)-) is an organic electronic material that can be used to form semiconductor charge transfer salts with electron accepting (n-type) materials (TCNQ and F4TCNQ). It can also be used to form charge transfer complexes (TCNQ and DDQ) with a variety of semiconductor crystals for the manufacture of organic field effect transistors (OFETs) and organic light emitting diodes (OLEDs).

Synthesis

Dibenzotetrathiafulvalene was prepared from 2,2'-Bi-1,3-benzodithiol under reaction conditions with  2,3-dicyano-5,6-dichloro-p-benzoquinone and dichloromethane. The specific method of operation is described below:
General procedure: Dithioacetal (0.1 mmol) and DDQ (68 mg, 0.30 mol) were dissolved in CH2Cl2 (3 mL). The resultant dark blue mixture was stirred at room temperature for 16 h and was then washed with a saturated NaOH aqueous solution (2 mL) and CH2Cl2 (10 mL). The orange organic phase was dried over anhydrous Na2SO4, filtered, and then evaporated under reduced pressure. The crude solid was recrystallized from hexane to give the corresponding dibenzotetrathiafulvalene derivative. Dibenzotetrathiafulvalene. Yield: 30 mg (99%); orange solid; mp 239.8-243.0 °C. 1H NMR (500 MHz, CDCl3): δ = 7.27-7.24 (m, 4 H), 7.13-7.10 (m, 4 H). 13C NMR (125 MHz, CDCl3): δ = 136.6, 125.9, 121.9, 110.6. MS (FAB): m/z = 304 [M+]. HRMS (FAB): m/z calcd for [M]+ (C14H8S4): 303.9509; found: 303.9519.