Influence of the boron moiety and water on suzuki-miyaura catalyst-transfer condensation polymerization.
Macromol Rapid Commun
; 36(4): 373-7, 2015 Feb.
Article
en En
| MEDLINE
| ID: mdl-25504582
ABSTRACT
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 (t) Bu3 PPd(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 H2 O/THF affords P3HT with a narrower molecular weight distribution and controlled tolyl/H ends, as compared to the reaction in dry THF.
Palabras clave
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Paladio
/
Boro
/
Agua
Idioma:
En
Revista:
Macromol Rapid Commun
Año:
2015
Tipo del documento:
Article
País de afiliación:
Japón