Universität zu Köln

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

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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:	Creators Email ORCID ORCID Put Code Welterlich, Irina UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Tieke, Bernd UNSPECIFIED UNSPECIFIED UNSPECIFIED
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
Uncontrolled Keywords:	Keywords Language MAIN-CHAIN; POLYMERS; UNITS; PIGMENTS; ACID Multiple languages Polymer Science Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/41748