DITHIENO[2,3-B:2',3'-D]THIOPHENE

Yellow to red solid

Dithieno[3,2-b:2′,3′-d]thiophene (DTT) is a conductive material that acts as a donor building block for synthesizing a variety of optoelectronic materials. It can be used as an active layer with high charge mobility and environmental stability for development of organic electronic devices.

113.0 g (0.397 mol) of the compound represented by the formula 3-d, 24.0 g (0.378 mol) of copper obtained in the above reaction scheme 18, and 791 mL of quinoline were placed in a 1 L round bottom flask and refluxed with stirring at 230 ° C. until the evolution of carbon dioxide . After the temperature was lowered to room temperature, the product was separated by column chromatography using hexane to obtain 58.8 g (75.4percent) of the compound represented by the formula 3-e.General procedure: To a 10 mL Schlenk flask were placed 3-phenoxybenzo[b]thiophene (45.3 mg, 0.2 mmol), Pd(TFA)General procedure: A mixture of 2, 5-di(hex-1-ynyl)-3, 4-diiodothiophene (1 g, 2.02 mmol), Na2S·9H2O (2.90 g, 12.12 mmol), CuI (0.0768 g, 0.403 mmol), and TMEDA (0.094 g, 0.806 mmol) in DMF (30 mL) was stirred at 80 °C for 24 h under a nitrogen atmosphere. Upon completion, the reaction mixture was extracted with Et2O (20 mL per time) until no product was observed in the extract, as monitored by TLC. The combined extract was washed with brine and dried with anhydrous MgSO4. After filtration, the solvent was removed and the residue was purified by chromatography on silica gel.Was charged in a dry, continuous nitrogen-fed reactorBromothiophene(8 ml, 0.08 mol), Ether (32 ml), The temperature was lowered to -78 ° C, n-butyllithium (32 ml, 0.08 mol) was added slowly, Stir for 40 minutes. Then, the temperature of the reaction solution was raised to 0 ° C, Under vacuumButyl bromide, Ether (32 ml) was added, The solution was cooled to -78 ° C, sulfur (2.56 g, 0.08 mol) was added and stirred for 30 minutes.The temperature was raised to 0 ° C, and the mixture was stirred for 30 minutesP-toluenesulfonyl chloride(15.22 g, 0.08 mol), The reaction was kept at 0 ° C for 30 minutes. The temperature was raised to 40 ° C, Insulate for 4 hours. A second portion was prepared according to the procedure described above3-lithium-thiophene (1.2 eq.), N-butyllithium (38.4 ml, 0.096 mol) and 3-bromothiophene (8.93 ml, 0.072 mol).The reaction solution was allowed to warm to 0 ° C and the butyl bromide was removed in vacuo and the ether was reintroduced. At -78 & lt; 0 &A second portion of a solution of 3-lithium-thiophene in diethyl ether was added to the first portion of the reaction solution, held for 1 hour, then allowed to warm to room temperature and allowed to react overnight.The reaction solution was cooled to 0 ° C the next day, and n-butyllithium (70.4 ml, 0.176 mol) was slowly added thereto, stirred for 30 minutes, and then refluxed for 1 hour. The temperature was lowered to 0C, Copper dichloride (24.42 g, 0.184 mol) was added, Stirred for 1 hour, then allowed to warm to room temperature and allowed to react overnight. The resulting solid was filtered and the organic phase was collected and purified by column chromatography (n-hexane). Recrystallization from n-hexane gave a pale yellow powder (4.74 g, yield 30.3percent).

DTT can be used for a wide range of applications which include electro-luminescence, organic thin film transistors, photochromism, and organic photovoltaic (OPV) solar cells.

Molecular Weight:196.3
XLogP3:3.8
Hydrogen Bond Acceptor Count:3
Exact Mass:195.94751365
Monoisotopic Mass:195.94751365
Topological Polar Surface Area:84.7
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes