Introduction of alkylsulfonic acid moieties into the side chain of polythiophene was carried out. Synthesis of 2,5-dihalothiophenes bearing alkylsulfonate groups at the 3-position was performed. The reaction of 2-chloro-5-iodothiophenes with Grignard reagents to form the organometallic monomers of the corresponding thiophenes followed by nickel(II)-catalyzed cross-coupling polymerization led to head-to-tail-type regioregular polythiophenes. The ester groups at the side chains were converted into alkali metal sulfonates by treatment with NaI or metal hydroxides (Li, Na, K). The obtained metal salts were successfully transformed into sulfonic acid groups by treatment with an ion exchange resin. The electric conductivity of the regioregular polythiophene bearing sulfonic acid groups was remarkably improved ca. 10² times compared to the corresponding metal salts (10⁶ times higher than the sulfonate ester).

中文翻译：

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侧链烷基磺酸酯聚噻吩的合成及性能

将烷基磺酸部分引入聚噻吩的侧链中。进行了在3-位带有烷基磺酸基团的2,5-二卤代噻吩的合成。 2-氯-5-碘噻吩与格氏试剂反应形成相应噻吩的有机金属单体，然后通过镍( II )催化的交叉偶联聚合产生头尾型区域规整聚噻吩。通过用 NaI 或金属氢氧化物（Li、Na、K）处理，侧链上的酯基转化为碱金属磺酸盐。通过离子交换树脂处理，所得金属盐成功转化为磺酸基。带有磺酸基团的立体规则聚噻吩的电导率显着提高约。是相应金属盐的10 ²倍（比磺酸酯高10 ^6倍）。