Synthesis and Supramolecular Organization of Regioregular Polythiophene Block Oligomers

被引：42

作者：

Clement, Sebastien ^{[1
,2
]}

Meyer, Franck ^{[1
]}

De Winter, Julien ^{[1
,6
]}

Coulembier, Olivier ^{[1
]}

Velde, Christophe M. L. Vande ^{[4
]}

Zeller, Matthias ^{[5
]}

Gerbaux, Pascal ^{[6
]}

Balandier, Jean-Yves ^{[2
]}

Sergeyev, Sergey ^{[2
,7
]}

Lazzaroni, Roberto ^{[3
]}

Geerts, Yves ^{[2
]}

Dubois, Philippe ^{[1
]}

机构：

[1] Univ Mons, CIRMAP, Lab Polymer & Composite Mat, B-7000 Mons, Belgium

[2] 1 Univ Libre Bruxelles, Fac Sci, Lab Chim Polymeres, B-1050 Brussels, Belgium

[3] Univ Mons, CIRMAP, Lab Chem Novel Mat, B-7000 Mons, Belgium

[4] Karel de Grote Univ Coll, Dept Appl Sci, Dept Appl Engn, B-2660 Antwerp, Belgium

[5] Youngstown State Univ, Dept Chem, Youngstown, OH 44555 USA

[6] Univ Mons, Mass Spectrometry Ctr, Organ Chem Lab, B-7000 Mons, Belgium

[7] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 05期

关键词：

CATALYST-TRANSFER POLYCONDENSATION; CHAIN-GROWTH POLYMERIZATION; WELL-DEFINED POLYTHIOPHENE; DOUBLE-CABLE POLYTHIOPHENE; ABSORPTION-SPECTROSCOPY; MICROPHASE SEPARATION; MOLECULAR DESIGN; SIDE-CHAINS; SOLID-STATE; GRIM METHOD;

D O I：

10.1021/jo902490m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The self-assembly of functional polythiophenes was studied by a bottom-up approach "from molecule to polymer". The synthesis and the X-ray structure of 2,5-dibromo-3-styryl and 3-2',3',4',5',6'-pentafluorostyryl-thiophenes revealed a supramolecular arrangement controlled by pi-pi interactions between the aromatic rings. A [2 + 2] photocyclization reaction in the solid state of (E)-1-2',5'-dibromo-3'-thienyl-2-phentafluorophenylethene triggers the formation of a rare cycloadduct comparing thiophene rings. The X-ray analysis confirmed its re11 stereochemistry. The synthesis of P3HT-b-P3ST and P3HT-b-P3STF block oligomers was acheived by a GRIM method in good yields. An indirect proof of well-defined nanostruactured organization was provided by the partial photocyclization of pendant styryl moieties under UV irradiation.

引用

页码：1561 / 1568

页数：8

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