Welterlich, Irina, Neudoerfl, Joerg-Martin and Tieke, Bernd (2015). Electrochemical polymerization of 1,3,4,6-tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP) derivatives. Polym. Chem., 6 (6). S. 1005 - 1014. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 1759-9962
Full text not available from this repository.Abstract
New pi-conjugated polymers containing 1,3,4,6-tetraarylpyrrolo[3,2-b] pyrrole-2,5-dione (isoDPP) units in the main chain were prepared by electrochemical polymerization of isoDPP-based monomers M1-M3. Monomers M1 and M2 were previously obtained upon palladium-catalyzed Suzuki cross-coupling of dibromo-isoDPP derivatives 3,6-bis(5-bromothiophen-2-yl)-1,4-bis(4-tert-butylphenyl) pyrrolo-[3,2-b]pyrrole-2,5-dione 1a, or 3,6-bis(5-bromothiophen-2-yl)-1,4-bis(4-hexylphenyl)-pyrrolo-[3,2-b] pyrrole2,5-dione 1b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-3-hexylthiophene. Monomer M3 was synthesized by Stille coupling of 1a and 2-(tributylstannyl)-4-octylthiophene. The yields were about 88%. M1-M3 were obtained as dark red powders with excellent solubility in organic solvents. The electrochemical polymerization was carried out under potentiodynamic conditions, i. e., the potential was repeatedly cycled between 0.0 (or -0.2) V and 1.2 V vs. ferrocene (FOC). The polymers P1-P3 precipitated as stable, insoluble, well adhering thin films on ITO-coated glass or glassy carbon electrodes. P1-P3 exhibit broad absorption spectra with maxima between 526 and 629 nm. They are non-fluorescent. Cyclovoltammetric studies indicate reversible oxidation and reduction behavior. Anodic cycling is accompanied with reversible colour changes of polymer films. The oxidation potentials are between 0.27 and 0.71 V vs. FOC, and the reduction potentials are between -1.21 and -1.69 V. The band gaps of the polymers are between 1.51 and 1.62 eV. Due to their optical and electrochemical properties the polymers might be useful as active materials in electrochromic displays.
Item Type: | Journal Article | ||||||||||||||||
Creators: |
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URN: | urn:nbn:de:hbz:38-417488 | ||||||||||||||||
DOI: | 10.1039/c4py01315h | ||||||||||||||||
Journal or Publication Title: | Polym. Chem. | ||||||||||||||||
Volume: | 6 | ||||||||||||||||
Number: | 6 | ||||||||||||||||
Page Range: | S. 1005 - 1014 | ||||||||||||||||
Date: | 2015 | ||||||||||||||||
Publisher: | ROYAL SOC CHEMISTRY | ||||||||||||||||
Place of Publication: | CAMBRIDGE | ||||||||||||||||
ISSN: | 1759-9962 | ||||||||||||||||
Language: | English | ||||||||||||||||
Faculty: | Unspecified | ||||||||||||||||
Divisions: | Unspecified | ||||||||||||||||
Subjects: | no entry | ||||||||||||||||
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URI: | http://kups.ub.uni-koeln.de/id/eprint/41748 |
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