Thienyl MIDA Boronate Esters as Highly Effective Monomers for Suzuki-Miyaura Polymerization Reactions
Thienyl MIDA Boronate Esters as Highly Effective Monomers for Suzuki-Miyaura Polymerization Reactions
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DOI：
10.1021/ma502542g
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发表时间：
2015-02-24
期刊：
影响因子：
5.5
通讯作者：
Turner, Michael L.
中科院分区：
文献类型：
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作者：
Carrillo, Josue Ayuso;Ingleson, Michael J.;Turner, Michael L.
报道了用Suzuki-Miyaura聚合法制备高度区域规则的聚（3-己基噻吩-2,5-二基）rr-P3HT。通过直接亲电硼酸化反应，采用一锅多图法合成了n -甲基氨基二乙酸（MIDA）硼酸酯硫烯基单体，纯度高，分离收率达80%。研究了MIDA保护基团水解和聚合反应的条件。最佳工艺使rr-P3HT具有>98%的HT偶联，分离收率高（高达94%），聚合物分子量高达M-n = 18.7 kDa, M-w = 42.7 kDa。在相同的聚合条件下，将含MIDA单体与硼酸匹纳考酯单体的性能进行了比较，后者产生的聚合物分子量更低，产率更低。
The synthesis of highly regioregular poly(3-hexylthiophene-2,5-diyl), rr-P3HT, by Suzuki-Miyaura polymerization is reported. The key N-methyliminodiacetic acid (MIDA) boronate ester thienyl monomer was synthesized using a one-pot multigram scale procedure, in high purity, and in good isolated yield (80%) by direct electrophilic borylation. Conditions for the hydrolysis of the MIDA protecting group and the polymerization reaction were investigated. The optimal procedure gave rr-P3HT with >98% HT couplings, excellent isolated yields (up to 94%), and polymer molecular weights up to M-n = 18.7 kDa and M-w = 42.7 kDa. The performance of the MIDA containing monomer was compared to that of the pinacol boronate ester under identical polymerization conditions, with the latter producing lower molecular weight polymers in reduced yield.