Rapid flow-based synthesis of poly(3-hexylthiophene) using 2-methyltetrahydrofuran as a bio-derived reaction solvent
| Autor: | Bannock, JH, Xu, W, Baïssas, T, Heeney, M, De Mello, JC |
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| Přispěvatelé: | Engineering & Physical Science Research Council (E, Engineering & Physical Science Research Council (EPSRC), Technology Strategy Board, Engineering and Physical Sciences Research Council |
| Jazyk: | angličtina |
| Předmět: |
Science & Technology
GRIGNARD METATHESIS EFFICIENCY POROUS CAPILLARY Polymers and Plastics IMPACT Polymers Organic Chemistry Polymer Science 0904 Chemical Engineering Physics and Astronomy(all) P3HT Green synthesis Semiconducting polymers ORGANIC SOLAR-CELLS DROPLET REACTOR CHEMISTRY Poly(3-hexylthiophene) Physical Sciences SEPARATION POLY(3-ALKYLTHIOPHENES) 0912 Materials Engineering Flow synthesis 0303 Macromolecular And Materials Chemistry |
| Zdroj: | European Polymer Journal. :240-246 |
| ISSN: | 0014-3057 |
| DOI: | 10.1016/j.eurpolymj.2016.04.016 |
| Popis: | We report the synthesis of poly(3-hexylthiophene) (P3HT) by Grignard metathesis (GRIM) polymerization using the bio-derived ‘green’ solvent 2-methyltetrahydrofuran (2-MeTHF). Using a standard flask-based reaction, the molecular weight distribution, regioregularity and product yield were found to be similar to those obtained under equivalent conditions using tetrahydrofuran (THF) as a reaction solvent. The synthesis was subsequently adapted to a novel “tube-in-shell” droplet-based flow reactor, using a newly developed high-solubility catalyst derived from nickel(II) bromide ethylene glycol dimethyl ether complex (Ni(dme)Br2) and 1,3-bis(diphenylphosphino)propane (dppp). Use of the new catalyst together with an increased reaction temperature of 65°C (enabled by the higher boiling point of 2-MeTHF) resulted in an approximate four-fold increase in reaction rate compared to a standard THF-based synthesis at 55°C, with full conversion reached within one minute. The purified flow-synthesized polymer had an Mw of 46kgmol−1, a low PDI of 1.4, and a regioregularity of 93%, indicating the suitability of flow-based GRIM polymerization in 2-MeTHF for the high-throughput synthesis of high quality P3HT. |
| Databáze: | OpenAIRE |
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