Synthesis of well-defined polythiophene with oxyethylene side chain: Effect of phosphine ligands on catalyst-transfer polycondensation

被引：63

作者：

Adachi, Isao ^{[1
]}

Miyakoshi, Ryo ^{[1
]}

Yokoyama, Akihiro ^{[1
]}

Yokozawa, Tsutomu ^{[1
]}

机构：

[1] Kanagawa Univ, Dept Mat & Life Chem, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan

来源：

MACROMOLECULES | 2006年 / 39卷 / 23期

关键词：

D O I：

10.1021/ma061809k

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

The effect of phosphine ligand of the Ni catalyst on the polymerization of 2-bromo-5-chloromagnesio-3-[2-(2-methoxyethoxy)ethoxy]-methylthiophene (PMEEMT) was investigated. Threatment of 2-bromo-5-iodo-3-[2-(2-methoxyethoxy)ethoxy]- methylthiophene with equivalent of isopropylmagnesium chloride at 0° C for 1 hour gave magnesium-iodine exchange reaction and the polymerization was carried out by the addition of Ni catalyst to the reaction mixture. The molecular weight increased linearly in proportion to the feed ratio and the molecular weight was controlled by the amount of catalyst. The end groups of PMEEMT were analyzed by matrix-assisted by laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry with dithranol as a matrix in the presence of sodium trifluoroacetate.

引用

页码：7793 / 7795

页数：3

共 18 条

[1] SOLUBLE, CONDUCTING POLYMERS FROM 3-SUBSTITUTED THIOPHENES AND PYRROLES [J].

BRYCE, MR ;

CHISSEL, A ;

KATHIRGAMANATHAN, P ;

PARKER, D ;

SMITH, NRM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (06) :466-467

[2] THE 1ST REGIOREGULAR HEAD-TO-TAIL POLY(3-HEXYLTHIOPHENE-2,5-DIYL) AND A REGIORANDOM ISOPOLYMER - NI VS PD CATALYSIS OF 2(5)-BROMO-5(2)-(BROMOZINCIO)-3-HEXYLTHIOPHENE POLYMERIZATION [J].

CHEN, TA ;

RIEKE, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (25) :10087-10088

[3] REGIOCONTROLLED SYNTHESIS OF POLY(3-ALKYLTHIOPHENES) MEDIATED BY RIEKE ZINC - THEIR CHARACTERIZATION AND SOLID-STATE PROPERTIES [J].

CHEN, TA ;

WU, XM ;

RIEKE, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :233-244

[4] Experimental evidence for the quasi-"living" nature of the grignard metathesis method for the synthesis of regioregular poly(3-alkylthiophenes) [J].

Iovu, MC ;

Sheina, EE ;

Gil, RR ;

McCullough, RD .

MACROMOLECULES, 2005, 38 (21) :8649-8656

[5] Regioregular, head-to-tail coupled poly(3-alkylthiophenes) made easy by the GRIM method: Investigation of the reaction and the origin of regioselectivity [J].

Loewe, RS ;

Ewbank, PC ;

Liu, JS ;

Zhai, L ;

McCullough, RD .

MACROMOLECULES, 2001, 34 (13) :4324-4333

[6] DESIGNING CONDUCTING POLYMER-BASED SENSORS - SELECTIVE IONOCHROMIC RESPONSE IN CROWN-ETHER CONTAINING POLYTHIOPHENES [J].

MARSELLA, MJ ;

SWAGER, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (25) :12214-12215

[7] DESIGN OF CHEMORESISTIVE SENSORY MATERIALS - POLYTHIOPHENE-BASED PSEUDOPOLYROTAXANES [J].

MARSELLA, MJ ;

CARROLL, PJ ;

SWAGER, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (39) :9832-9841

[8] DESIGN, SYNTHESIS, AND CONTROL OF CONDUCTING POLYMER ARCHITECTURES - STRUCTURALLY HOMOGENEOUS POLY(3-ALKYLTHIOPHENES) [J].

MCCULLOUGH, RD ;

LOWE, RD ;

JAYARAMAN, M ;

ANDERSON, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :904-912

[9] ENHANCED ELECTRICAL-CONDUCTIVITY IN REGIOSELECTIVELY SYNTHESIZED POLY(3-ALKYLTHIOPHENES) [J].

MCCULLOUGH, RD ;

LOWE, RD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (01) :70-72

[10] TOWARD TUNING ELECTRICAL AND OPTICAL-PROPERTIES IN CONJUGATED POLYMERS USING SIDE-CHAINS - HIGHLY CONDUCTIVE HEAD-TO-TAIL HETEROATOM-FUNCTIONALIZED POLYTHIOPHENES [J].

MCCULLOUGH, RD ;

WILLIAMS, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11608-11609

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