A General Protocol for the Polycondensation of Thienyl N-Methyliminodiacetic Acid Boronate Esters To Form High Molecular Weight Copolymers.
A General Protocol for the Polycondensation of Thienyl N-Methyliminodiacetic Acid Boronate Esters To Form High Molecular Weight Copolymers.
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DOI：
10.1021/jacs.6b07666
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发表时间：
2016-10-12
影响因子：
15
通讯作者：
Ingleson MJ
中科院分区：
文献类型：
--
作者：
Carrillo JA;Turner ML;Ingleson MJ
噻吩基二-N-甲基亚氨基二乙酸（MIDA）硼酸酯易于通过亲电C-H硼基化反应合成，以良好的产率和优异的纯度产生稳定的结晶固体。在两相THF/水混合物中使用KOH作为碱缓慢释放硼酸的最佳条件使得噻吩基MIDA硼酸酯在与二溴杂芳烃（BB型单体）的Suzuki-Miyaura共聚中成为极其有效的均双官能化（AA型）单体。单一聚合方案适用于形成五种交替噻吩基共聚物，所述共聚物是有机电子中使用的现有技术材料（或其类似物）。这五种聚合物以优异的产率生产，并且具有与使用Stille共聚方案生产的那些相当的高分子量。因此，噻吩基二-MIDA硼酸酯代表了高毒性二-三甲基甲锡烷基AA型单体的实验室稳定和低毒性的替代品，所述高毒性二-三甲基甲锡烷基AA型单体目前普遍存在于这些重要的交替共聚物的合成中。
Thienyl di-N-methyliminodiacetic acid (MIDA) boronate esters are readily synthesized by electrophilic C–H borylation producing bench stable crystalline solids in good yield and excellent purity. Optimal conditions for the slow release of the boronic acid using KOH as the base in biphasic THF/water mixtures enables the thienyl MIDA boronate esters to be extremely effective homo-bifunctionalized (AA-type) monomers in Suzuki–Miyaura copolymerizations with dibromo-heteroarenes (BB-type monomers). A single polymerization protocol is applicable for the formation of five alternating thienyl copolymers that are (or are close analogues of) state of the art materials used in organic electronics. The five polymers were produced in excellent yields and with high molecular weights comparable to those produced using Stille copolymerization protocols. Therefore, thienyl di-MIDA boronate esters represent bench stable and low toxicity alternatives to highly toxic di-trimethylstannyl AA-type monomers that are currently ubiquitous in the synthesis of these important alternating copolymers.
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