Synthesis of Poly(3-substituted thiophene)s of Remarkably High Solubility in Hydrocarbon via Nickel-Catalyzed Deprotonative Cross-Coupling Polycondensation
| Autor: | Takeshi Yasuda, Keisuke Fujita, Atsunori Mori, Shunsuke Tamba, Kenji Ide, Keisuke Shono, Jian Shen, Takashi Nishino, Yugo Sumino |
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| Rok vydání: | 2016 |
| Předmět: |
Condensation polymer
Polymers and Plastics 010405 organic chemistry Organic Chemistry Substituent 010402 general chemistry 01 natural sciences 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound Monomer chemistry Polymerization Siloxane Polymer chemistry Materials Chemistry Thiophene Moiety Molar mass distribution |
| Zdroj: | Macromolecules. 49:1259-1269 |
| ISSN: | 1520-5835 0024-9297 |
| DOI: | 10.1021/acs.macromol.5b02524 |
| Popis: | Polythiophenes bearing a siloxane moiety in a substituent at the 3-position are prepared by deprotonative polycondensation of 2-bromo-3-substituted-thiophene with a bulky magnesium amide chloromagnesium 2,2,6,6-tetramethylpiperidine-1-yl lithium chloride salt (TMPMgCl·LiCl) catalyzed by a nickel complex. Deprotonation takes place at 60 °C for 1 h to form the corresponding thiophene magnesium species, which is subjected to the polymerization by addition of 0.1–5 mol % NiCl2(PPh3)IPr (IPr: 1,3-bis(2,6-diisopropylphenyl)imidazole-2-yl). Polymerization proceeds in a highly regioregular manner, and the molecular weight of the thus-obtained polymer is controllable by the ratio of monomer feed/catalyst loading to indicate Mn of up to 280 000 with narrow molecular weight distribution. Chlorothiophenes are also found to induce polymerization in a deprotonative manner with TMPMgCl·LiCl or nBuLi (the Murahashi coupling polymerization). The obtained polymers bearing a siloxane moiety in the substituent is revealed to... |
| Databáze: | OpenAIRE |
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