Zhang, Haichang, Ying, Shian, Tieke, Bernd, Zhang, Jun and Yang, Wenjun (2015). 1,6-Naphthodipyrrolidone-based donor acceptor polymers with low bandgap. Polymer, 60. S. 215 - 221. OXFORD: ELSEVIER SCI LTD. ISSN 1873-2291

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Abstract

Donor acceptor CD A) copolymers P1-P4 containing 1,6-naphthodipyrrolidone as acceptor unit are synthesized and characterized. Copolymers P1 and P2 are prepared upon Suzuki coupling of 3,8-di(4bromophenyl)-1.6-bis(dodecyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole (M1) or 3,8di-(4-bromophenyl)-1.6-bis(2-octyldodecyl)-2,7-dioxo-1,2,6,7-tetrahydronaphtho[1,2-b:5,6-b']dipyrrole (M2) with the donor comonomer 2,2-(9,9-dioctyl-9H-fluoren-2,7-diyl)-bis-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (M3). Polymers P3 and P4 are prepared upon Stille coupling of M1 or M2 with the donor comonomer 4,8-bis(2-ethylhexyloxy)benzo[1,2-6:4,5-6]dithiophene-2,6-diyl-bistrimethyl-stannane M4. The two monomers M1 and M2 exhibit a deep purple color in dichloromethane with high extinction coefficients up to 4.9*10(4) L mol(-1) cm(-1). Optical, electrochemical and thermal properties of the polymers are characterized. The polymers exhibit a broad UV/vis absorption range from 400 to 850 nm, low optical bandgaps (1.27-1.47 eV), low LUMO levels (especially for P1 and P2), a high thermal stability with glass temperature T-g up to 224 degrees C, and 5% weight loss up to 402 degrees C. Density functional theory calculations indicate that the backbone of the 1,6-NDP-polymers is rather planar. Photostability studies indicate a high stability against UV-irradiation in the solid state, but only a moderate stability upon UV irradiation in solution. (C) 2015 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Zhang, HaichangUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Ying, ShianUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Tieke, BerndUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Zhang, JunUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Yang, WenjunUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-409921
DOI: 10.1016/j.polymer.2015.01.035
Journal or Publication Title: Polymer
Volume: 60
Page Range: S. 215 - 221
Date: 2015
Publisher: ELSEVIER SCI LTD
Place of Publication: OXFORD
ISSN: 1873-2291
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
ORGANIC PHOTOVOLTAICS; CONJUGATED POLYMERS; UNITSMultiple languages
Polymer ScienceMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/40992

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