Universität zu Köln

Zhang, Haichang, Welterlich, Irina, Neudoerfl, Joerg-Martin, Tieke, Bernd, Yang, Chao, Chen, Xuegang and Yang, Wenjun (2013). Synthesis and characterization of 1,3,4,6-tetraarylpyrrolo[3,2-b]-pyrrole-2,5-dione (isoDPP)-based donor-acceptor polymers with low band gap. Polym. Chem., 4 (17). S. 4682 - 4690. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 1759-9962

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Abstract

The synthesis of new pi-conjugated donor-acceptor (D-A) polymers containing tetraaryl-diketopyrrolo[3,2-b]-pyrrole (isoDPP) as the building block is described. Polymers were prepared upon palladium-catalyzed Stille coupling of 3,6-bis(5-bromothien-2-yl)-1,4-diphenyl-pyrrolo[3,2-b]pyrrole-2,5-dione (M1) with 4,4'-bis(2-ethylhexyl)-5,5'-bis(trimethyltin)dithieno[3,2-b:2',3'-d]silole (M2) or (4,8-bis-(2-ethylhexyloxy)benzo [1,2-b:4,5-b]dithiophene-2,6-diyl)bis(trimethylstannane) (M3). The polymers exhibit low band gaps of 1.53 and 1.67 eV, broad absorption bands with maxima of 523 nm and 620 nm, and high extinction coefficients of 6.5 x 10(4) L mol(-1) cm(-1), and 2.6 x 10(4) L mol(-1) cm(-1), respectively. Low fluorescence quantum yields between 0.13% and 0.82% were detected. Quantum chemical calculations indicated a nearly planar backbone with highly delocalized HOMO orbitals and localization of the LUMO electrons at the thienyl-isoDPP units. The X-ray structure analysis of M1 indicated a dihedral angle of 14.1 degrees between the thienyl groups and the isoDPP core, and a 76.6 degrees dihedral angle of the lactam phenyl group and the isoDPP core, the latter preventing any pi-stacking of the monomers. The polymers show high glass transitions (T-g) and excellent thermal stability. Photoirradiation studies indicate that the polymers are extremely stable to UV and visible light in solution. Spectroelectrochemical studies indicated a reversible electrochromism with isosbestic point near 710 nm.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Zhang, Haichang UNSPECIFIED UNSPECIFIED UNSPECIFIED Welterlich, Irina UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Tieke, Bernd UNSPECIFIED UNSPECIFIED UNSPECIFIED Yang, Chao UNSPECIFIED UNSPECIFIED UNSPECIFIED Chen, Xuegang UNSPECIFIED UNSPECIFIED UNSPECIFIED Yang, Wenjun UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-475869
DOI:	10.1039/c3py00570d
Journal or Publication Title:	Polym. Chem.
Volume:	4
Number:	17
Page Range:	S. 4682 - 4690
Date:	2013
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
ISSN:	1759-9962
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language CONJUGATED POLYMERS; PHOTOVOLTAIC CELLS; ELECTROCHEMICAL POLYMERIZATION; SOLAR-CELLS; COPOLYMERS; DITHIENOSILOLE; SUBSTITUTION; ORGANIZATION; LUMINESCENT; EFFICIENCY Multiple languages Polymer Science Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/47586