Synthesis of a 1,2-Dithienylethene-Containing Donor-Acceptor Polymer via Palladium-Catalyzed Direct Arylation Polymerization (DArP)

Masayuki Wakioka, Natsumi Yamashita, Hiroki Mori, Yasushi Nishihara, Fumiyuki Ozawa

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

This paper reports the synthesis of D-A polymers containing 1,2-dithienylethene (DTE) units via palladium-catalyzed direct arylation polymerization (DArP). The reaction of dibromoisoindigo (1-Br) and DTE (2-H), in the presence of Pd2(dba)3·CHCl3 (0.5 mol%), P(2-MeOC6H4)3 (L1) (2 mol%), pivalic acid (1 equiv) as catalyst precursors, and Cs2CO3 (3 equiv) as a base affords poly(1-alt-2) with a high molecular weight (Mn up to 44,900). Although, it has been known that monomers, with plural C–H bonds, tend to form insoluble materials via direct arylation at undesirable C–H positions; the reaction of 1-Br and 2-H cleanly proceeds without insolubilization. The resulting polymer has a well-controlled structure and exhibits good charge transfer characteristics in an organic field-effect transistor (OFET), compared to the polymer produced by Migita–Kosugi–Stille cross-coupling polymerization. The DArP product displays an ideal linear relationship in the current–voltage curve, whereas the Migita–Kosugi–Stille product shows a VG-dependent change in the charge mobility.

Original languageEnglish
Article number981
JournalMolecules
Volume23
Issue number4
DOIs
Publication statusPublished - Jan 1 2018

Fingerprint

Palladium
Polymerization
palladium
Polymers
polymerization
polymers
synthesis
methylidyne
Organic field effect transistors
cross coupling
products
Charge transfer
molecular weight
field effect transistors
monomers
Monomers
Molecular Weight
Molecular weight
charge transfer
catalysts

Keywords

  • Conjugated polymer
  • Direct arylation
  • Palladium catalyst
  • Polycondensation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of a 1,2-Dithienylethene-Containing Donor-Acceptor Polymer via Palladium-Catalyzed Direct Arylation Polymerization (DArP). / Wakioka, Masayuki; Yamashita, Natsumi; Mori, Hiroki; Nishihara, Yasushi; Ozawa, Fumiyuki.

In: Molecules, Vol. 23, No. 4, 981, 01.01.2018.

Research output: Contribution to journalArticle

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