期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 40, 页码 13361-13368出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07666
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资金
- Conacyt [311311]
- EPSRC [EP/K03099X/1, EP/K039547/1]
- ERC [305868]
- Royal Society
- InnovateUK
- European Research Council (ERC) [305868] Funding Source: European Research Council (ERC)
- Engineering and Physical Sciences Research Council [EP/K03099X/1, EP/K039547/1] Funding Source: researchfish
- EPSRC [EP/K039547/1, EP/K03099X/1] Funding Source: UKRI
Thienyl di-N-methyliminodiacetic add (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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