Low-temperature side-chain cleavage and decarboxylation of polythiophene esters by acid catalysis

被引:14
作者
Sondergaard, Roar R. [1 ]
Norrman, Kion [1 ]
Krebs, Frederik C. [1 ]
机构
[1] Tech Univ Denmark, Riso Natl Lab Sustainable Energy, DK-4000 Roskilde, Denmark
关键词
acid catalysis; conducting polymers; catalysis; decarboxylation; ester cleavage; low temperature; polythiophene ester; primary ester; secondary ester; solubility switching; tertiary ester; thermocleavage; thermogravimetric analysis (TGA); SOLAR-CELLS; POLYMERS;
D O I
10.1002/pola.25870
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Solubility switching of polymers is very useful in thin layer processing of conjugated polymers, as it allows for multilayer processing and increases the stability of the polymer. Acid catalyzed thermocleavage of ester groups from thiophene polymers carrying primary, secondary, and tertiary substituents have been examined by TGA-MS using different sulphonic acids. A substantial lowering of the cleavage temperature is observed, and the ester cleavage can even be performed in situ on roll-to-roll-coated films on polyethylene terephthalate (PET). (c) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
引用
收藏
页码:1127 / 1132
页数:6
相关论文
共 20 条
[1]   An explanation for the high stability of polycarboxythiophenes in photovoltaic devices- A solid-state NMR dipolar recoupling study [J].
Bierring, Morten ;
Nielsen, Julie S. ;
Siu, Ana ;
Nielsen, Niels Chr. ;
Krebs, Frederik C. .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2008, 92 (07) :772-784
[2]   Polythiophene by solution processing [J].
Bjerring, Morten ;
Nielsen, Julie Sogaard ;
Nielsen, Niels Chr. ;
Krebs, Frederik C. .
MACROMOLECULES, 2007, 40 (16) :6012-6013
[3]   A deeper Insight into the Dithiocarbamate Precursor Route Synthesis of Soluble Poly(thienylene vinylene) Derivatives for Photovoltaic Applications [J].
Dilien, Hanne ;
Palmaerts, Arne ;
Lenes, Martijin ;
de Boer, Bert ;
Blom, Paul ;
Cleij, Thomas J. ;
Lutsen, Laurence ;
Vanderzande, Dirk .
MACROMOLECULES, 2010, 43 (24) :10231-10240
[4]   An Efficient Acid-Induced Conversion of Dithiocarbamate Precursor Polymers into Conjugated Materials [J].
Dilien, Hanne ;
Vandenbergh, Joke ;
Banishoeb, Fateme ;
Adriaensens, Peter ;
Cleij, Thomas J. ;
Lutsen, Laurence ;
Vanderzande, Dirk J. M. .
MACROMOLECULES, 2011, 44 (04) :711-718
[5]   KINETICS AND MECHANISM OF DECARBOXYLATION OF PYRROLE-2-CARBOXYLIC ACID IN AQUEOUS SOLUTION [J].
DUNN, GE ;
LEE, GKJ .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (07) :1032-&
[6]   Benzothiadiazole- and pyrrole-based polymers bearing thermally cleavable solubilizing groups as precursors for low bandgap polymers [J].
Edder, C ;
Armstrong, PB ;
Prado, KB ;
Fréchet, JMJ .
CHEMICAL COMMUNICATIONS, 2006, (18) :1965-1967
[7]   Bulk heterojunctions based on native polythiophene [J].
Gevorgyan, Suren A. ;
Krebs, Frederik C. .
CHEMISTRY OF MATERIALS, 2008, 20 (13) :4386-4390
[8]   All solution processed tandem polymer solar cells based on thermocleavable materials [J].
Hagemann, Ole ;
Bjerring, Morten ;
Nielsen, Niels Chr. ;
Krebs, Frederik C. .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2008, 92 (11) :1327-1335
[9]   Nanostructured morphologies and topologies of π-conjugated polymers from thermally reactive polymer blends [J].
Han, Xu ;
Chen, Xiwen ;
Holdcroft, Steven .
ADVANCED MATERIALS, 2007, 19 (13) :1697-+
[10]   Substituted 2,1,3-Benzothiadiazole- And Thiophene-Based Polymers for Solar Cells - Introducing a New Thermocleavable Precursor [J].
Helgesen, Martin ;
Gevorgyan, Suren A. ;
Krebs, Frederik C. ;
Janssen, Rene A. J. .
CHEMISTRY OF MATERIALS, 2009, 21 (19) :4669-4675