Precision Synthesis of Poly(3‐hexylthiophene) from Catalyst‐Transfer Suzuki−Miyaura Coupling Polymerization
Identifieur interne : 000D20 ( Main/Exploration ); précédent : 000D19; suivant : 000D21Precision Synthesis of Poly(3‐hexylthiophene) from Catalyst‐Transfer Suzuki−Miyaura Coupling Polymerization
Auteurs : Tsutomu Yokozawa [Japon] ; Ryosuke Suzuki [Japon] ; Masataka Nojima [Japon] ; Yoshihiro Ohta [Japon] ; Akihiro Yokoyama [Japon]Source :
- Macromolecular Rapid Communications [ 1022-1336 ] ; 2011-06-01.
English descriptors
- Teeft :
- Block copolymerization, Block copolymers, Cdcl3, Chem, Commun, Complex initiator, Condensation polymerization, Copolymer, Feed ratio, High ratio, Hydrogen atom, Kiriy, Macromol, Macromolecule, Mass spectra, Mmol, Monomer, Organic layer, P3ht, Phenyl group, Polymer, Polymerization, Polymerization manner, Rapid commun, Reaction mixture, Senkovskyy, Suzuki, Thiophene monomer, Uorene monomer, Verlag gmbh, Weinheim, Yokoyama, Yokozawa.
Abstract
tBu3 PPd(Ph)Br (1)‐catalyzed Suzuki‐Miyaura coupling polymerization of 2‐(4‐hexyl‐5‐iodo‐2‐thienyl)‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane (2) was investigated. Monomer 2 was polymerized with 1 at 0 °C in the presence of CsF and 18‐crown‐6 in THF containing a small amount of water to yield P3HT with a narrow molecular weight distribution and almost perfect head‐to‐tail regioregularity. The $\overline {M} _{{\rm n}} $ values increased up to 11 400 g · mol−1 in proportion to the feed ratio of 2 to 1. The MALDI‐TOF mass spectra showed that P3HT with moderate molecular weight uniformly had a phenyl group at one end and a hydrogen atom at the other, indicating involvement of a catalyst‐transfer mechanism. Successive 1‐catalyzed polymerization of fluorene monomer 3 and then 2 yielded a well‐defined block copolymer of polyfluorene and P3HT.
Suzuki‐Miyaura coupling polymerization of 2‐(4‐hexyl‐5‐iodo‐2‐thienyl)‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane (2) with tBu3PPd(Ph)Br (1) proceeds at 0°C in the presence of CsF and 18‐crown‐6 to yield P3HT with controlled molecular weight up to 11400 g·mol−1 and almost perfect head‐to‐tail regioregularity. Successive 1 ‐catalyzed polymerization of fluorene monomer 3 and then 2 yielded well‐defined block copolymer of polyfluorene and P3HT.
Url:
DOI: 10.1002/marc.201100037
Affiliations:
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gmbh</term><term>Weinheim</term><term>Yokoyama</term><term>Yokozawa</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">tBu3 PPd(Ph)Br (1)‐catalyzed Suzuki‐Miyaura coupling polymerization of 2‐(4‐hexyl‐5‐iodo‐2‐thienyl)‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane (2) was investigated. Monomer 2 was polymerized with 1 at 0 °C in the presence of CsF and 18‐crown‐6 in THF containing a small amount of water to yield P3HT with a narrow molecular weight distribution and almost perfect head‐to‐tail regioregularity. The $\overline {M} _{{\rm n}} $ values increased up to 11 400 g · mol−1 in proportion to the feed ratio of 2 to 1. The MALDI‐TOF mass spectra showed that P3HT with moderate molecular weight uniformly had a phenyl group at one end and a hydrogen atom at the other, indicating involvement of a catalyst‐transfer mechanism. Successive 1‐catalyzed polymerization of fluorene monomer 3 and then 2 yielded a well‐defined block copolymer of polyfluorene and P3HT.</div><div type="abstract" xml:lang="en">Suzuki‐Miyaura coupling polymerization of 2‐(4‐hexyl‐5‐iodo‐2‐thienyl)‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane (2) with tBu3PPd(Ph)Br (1) proceeds at 0°C in the presence of CsF and 18‐crown‐6 to yield P3HT with controlled molecular weight up to 11400 g·mol−1 and almost perfect head‐to‐tail regioregularity. Successive 1 ‐catalyzed polymerization of fluorene monomer 3 and then 2 yielded well‐defined block copolymer of polyfluorene and P3HT.</div></front></TEI><affiliations><list><country><li>Japon</li></country></list><tree><country name="Japon"><noRegion><name sortKey="Yokozawa, Tsutomu" sort="Yokozawa, Tsutomu" uniqKey="Yokozawa T" first="Tsutomu" last="Yokozawa">Tsutomu Yokozawa</name></noRegion><name sortKey="Nojima, Masataka" sort="Nojima, Masataka" uniqKey="Nojima M" first="Masataka" last="Nojima">Masataka Nojima</name><name sortKey="Ohta, Yoshihiro" sort="Ohta, Yoshihiro" uniqKey="Ohta Y" first="Yoshihiro" last="Ohta">Yoshihiro Ohta</name><name sortKey="Suzuki, Ryosuke" sort="Suzuki, Ryosuke" uniqKey="Suzuki R" first="Ryosuke" last="Suzuki">Ryosuke Suzuki</name><name sortKey="Yokoyama, Akihiro" sort="Yokoyama, Akihiro" uniqKey="Yokoyama A" first="Akihiro" last="Yokoyama">Akihiro Yokoyama</name><name sortKey="Yokozawa, Tsutomu" sort="Yokozawa, Tsutomu" uniqKey="Yokozawa T" first="Tsutomu" last="Yokozawa">Tsutomu Yokozawa</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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