Synthesis of a Bithiophene-Isoindigo-Based π-Conjugated Polymer <i>via</i> Direct Arylation Polycondensation Using Palladium Immobilized on Thiol-modified Silica Gel (PITS)

• HAYASHI Shotaro

  Department of Applied Chemistry, National Defense Academy

• KOIZUMI Toshio

  Department of Applied Chemistry, National Defense Academy

Bibliographic Information

Other Title

• チオール修飾シリカゲルに固定したパラジウム(PITS)を触媒とした直接的アリール化重縮合によるビチオフェン―イソインジゴπ共役系高分子の合成
• チオール シュウショク シリカゲル ニ コテイ シタ パラジウム(PITS)オ ショクバイ ト シタ チョクセツテキ アリールカジュウ シュクゴウ ニ ヨル ビチオフェン-イソインジゴpキョウヤクケイ コウブンシ ノ ゴウセイ

Abstract

The direct arylation polycondensation of 3,3′-dihexyl-2,2′-bithiophene (BT6) with dibromoisoindigo (ID) was achieved by using PITS, palladium immobilized on thiol-modified silica gel. The polycondensation of BT6 with ID using PdCl₂ for 1 h gave PBT6ID (M_n = 6900) in 74% yield. On the other hand, the polycondensation for 2 h gave PBT6ID (M_n = 5600) in low (12%) yield along with insoluble polymer products. This is probably due to chain branching based on β-defects of the polymers. The polycondensation of BT6 with ID for 12 h was performed with PITS-Cl catalyst, furnishing PBT6ID (M_n = 9800) in 79% yield. The optical and electrochemical properties of PBT6ID are also described.

Journal

• KOBUNSHI RONBUNSHU

  KOBUNSHI RONBUNSHU 74 (6), 584-587, 2017

  The Society of Polymer Science, Japan

Keywords

• Conjugated Polymers
• Isoindigo
• Direct Arylation
• Palladium

Details

• CRID: 1390001206525394816
• NII Article ID: 130006218873
• NII Book ID: AN00085011
• DOI: 10.1295/koron.2017-0029
• ISSN: 18815685
• ISSN: 03862186
• NDL BIB ID: 028675800
• Web Site: http://id.ndl.go.jp/bib/028675800
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I028675800
• Web Site: https://www.jstage.jst.go.jp/article/koron/74/6/74_2017-0029/_pdf
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed