Chemical Properties
clear colorless to yellow liquid
Uses
Conducting polymer precursor.
Uses
3-Dodecylthiophene is a reactant used to make semiconducting copolymers.
Preparation
3-Dodecylthiophene can be prepared from 3-bromothiophene and halogenated hydrocarbons in one step.
Steps: Under N2 atmosphere, slowly add 1-bromododecane (28.75g, 26.9 mL) to a 250mL three-necked flask containing a mixture of magnesium chips (3.28g, 0.135mol), anhydrous THF (30mL) and a small amount of iodine. mL, 0.13 mol) in dry THF (45 mL). After the mixture was refluxed at 70 °C for 2 hours, the system was cooled to room temperature with ice water, Ni(dppp)Cl2 (0.54 g, 1.00 mmol) was added first, and then 3-bromothiophene (16.31 g, 0.10 mol) was added slowly. Anhydrous THF (40 mL) solution. The mixed solution was stirred at room temperature overnight, and cold aqueous HCl (1.50 mol/L) was added to quench the reaction. The crude product was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and further purified by column separation purification (n-hexane as eluent), resulting in a clear liquid (22.18 g, yield=88%).
General Description
3-Dodecylthiophene (3-DT) is a conjugating monomer that can be used as an active layer on semiconductors. It has good electronic properties and can be used in the development of p-type semiconducting polymers. It is mainly used in the formation of poly(3-dodecylthiophene) (P3DT) through electrochemical polymerization. P3DT can further be utilized for a variety of organic electronic based applications.
Synthesis
Anhydrous THF (30 mL) was added to a 250 mL three-necked flask containing magnesium flakes (3.28 g, 0.135 mol) and a small amount of iodine under nitrogen atmosphere. Subsequently, 1-bromododecane (28.75 g, 26.9 mL, 0.13 mol) dissolved in anhydrous THF (45 mL) was added slowly and dropwise. The reaction mixture was refluxed at 70 °C for 2 hours. After completion of the reaction, the system was cooled to room temperature using an ice water bath and Ni(dppp)Cl2 (0.54 g, 1.00 mmol) was added as a catalyst. Next, 3-bromothiophene (16.31 g, 0.10 mol) dissolved in anhydrous THF (40 mL) was slowly added. The mixed solution was stirred at room temperature overnight. At the end of the reaction, the reaction was quenched with cold 1.50 mol/L HCl aqueous solution. The crude product was extracted with dichloromethane, and the organic phase was dried with anhydrous magnesium sulfate, filtered and purified by column chromatography (with hexane as eluent) to give the clarified liquid product 3-dodecylthiophene (22.18 g, 88% yield).
References
[1] Patent: CN106588867, 2017, A. Location in patent: Paragraph 0022; 0023; 0024
[2] Journal of Physical Chemistry B, 2001, vol. 105, # 45, p. 11106 - 11113
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 18, p. 3942 - 3949
[4] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 5, p. 1659 - 1663
[5] Angewandte Chemie - International Edition, 2018, vol. 57, # 24, p. 7034 - 7039
