Detailed optimization of polycondensation reaction via direct C-H arylation of ethylenedioxythiophene.
The polycondensation reaction of 3,4-ethylenedioxythiophene with 2,7-dibromo-9,9-dioctylfluorene via Pd-catalyzed direct arylation gives poly[(3,4-ethylenedioxythiophene-2,5-diyl)-(9,9-dioctylfluorene-2,7-diyl)]. The reaction conditions are optimized in terms of the Pd precatalysts, reaction time, and carboxylic acid additives. The combination of 1 mol% Pd(OAc)(2) and 1-adamantanecarboxylic acid as an additive is the optimized catalytic system, and it yields the corresponding polymer with a molecular weight of 39,400 in 89% yield. The polycondensation reaction, followed by an end-capping reaction, effectively provides a linear polymer without Br terminals.
Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Japan.
Koutarou
K
Yamazaki
Junpei
J
Kuwabara
Takaki
T
Kanbara
D002244:Carbon / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D010165:Palladium; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry*
D002264:Carboxylic Acids; D011108:Polymers; D013876:Thiophenes; D010165:Palladium; D002244:Carbon; D006859:Hydrogen