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HomeProduct name listDibenzotetrathiafulvalene

Dibenzotetrathiafulvalene

Synonym(s):[2,2’]Bi[benzo[1,3]dithiolylidene];DBTTF

Dibenzotetrathiafulvalene Structural

What is Dibenzotetrathiafulvalene?

The Uses of Dibenzotetrathiafulvalene

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.
1,3-Benzodithiole,2-(1,3-benzodithiol-2-ylidene)- synthesis

Properties of Dibenzotetrathiafulvalene

Melting point: 239-243 °C
Boiling point: 367.1±42.0 °C(Predicted)
Density  1.538±0.06 g/cm3(Predicted)

Safety information for Dibenzotetrathiafulvalene

Signal word Warning
Pictogram(s)
ghs
Environment
GHS09
GHS Hazard Statements H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P273:Avoid release to the environment.
P501:Dispose of contents/container to..…

Computed Descriptors for Dibenzotetrathiafulvalene

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