SYNTHESIS OF ALKYL SUBSTITUTED ETHYL 2,2':5',2'':5'',2'''-QUATERTHIOPHENE-5- AND 5-(BIPHENYL-4-YL)THIOPHENE-2-CARBOXYLATES
DOI:
https://doi.org/10.1007/3441Keywords:
5-(biphenyl-4-yl)-4-decylthiophene-2-carboxylic acid, 3-decyl-2, 2', 5', 2'', 5'', 2'''-quaterthiophene-5-carboxylic acid, organic electronics, Fiesselmann reactionAbstract
Acylation of 2,2':5',2''-terthiophene and biphenyl gave 1-(2,2':5',2''-terthiophene-5-yl)dodecan-1-one and 1-(biphenyl-4-yl)dodecan-1-one, which upon treatment with phosphorus oxychloride and dimethylformamide were converted to 2-[(2,2':5',2''-terthiophene-5-yl)chloromethylidene]dodecanal and 2-[(biphenyl-4-yl)chloromethylidene]dodecanal. The reaction of these compounds with ethyl 2mercaptoacetate led to the formation of ethyl 3-decyl-2,2':5',2'':5'',2'''-quaterthiophene-5- and 5-(biphenyl-4-yl)-4decylthiophene-2-carboxylates, which are of interest as building blocks for the synthesis of organic semiconductors. Ethyl 3-decyl-2,2':5',2'':5'',2'''-quaterthiophene-5-carboxylate was also obtained by palladium-catalyzed cross-coupling of ethyl 5'-bromo-3-decyl-2,2'-bithiophene-5-carboxylate with 2,2'-bithiophene.
Authors: Anastasia S. Kostyuchenko, Ekaterina A. Drozdova, Alexander S. Fisyuk*
