期刊
MACROMOLECULAR RAPID COMMUNICATIONS
卷 36, 期 4, 页码 373-377出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/marc.201400530
关键词
catalyst-transfer condensation polymerization; palladium catalyst; polythiophenes; Suzuki polycondensation; triolborate
资金
- MEXT
- Grants-in-Aid for Scientific Research [24550141] Funding Source: KAKEN
Although water promotes Suzuki-Miyaura coupling reaction, it also induces side reactions such as deboronation and dehalogenation. Therefore, Suzuki-Miyaura polymerization of triolborate halothiophene monomer 1 with (Bu3PPd)-Bu-t(o-tolyl)Br (2) in dry tetrahydrofuran (THF) is investigated. However, the resultant poly(3-hexylthiophene) (P3HT) shows a broad molecular weight distribution and uncontrolled polymer ends. Model reactions of a number of boron reagents 3 with 2,5-dibromothiophene (4) in the presence or absence of water indicate that intramolecular transfer of the catalyst is hardly affected by the boron moiety of 3, whereas it is hindered in the absence of water. Indeed, polymerization of 1 with 2 in H2O/THF affords P3HT with a narrower molecular weight distribution and controlled tolyl/H ends, as compared to the reaction in dry THF.
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