Zhang, Haichang, Zhang, Jun and Tieke, Bernd (2014). A comparative study of polymers containing naphthodifuranone and benzodifuranone units in the main chain. Polym. Chem., 5 (2). S. 646 - 653. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 1759-9962

Full text not available from this repository.

Abstract

The synthesis of two new polymers containing the naphtho[2,1-b:3,4-b']difuran-2,9-dione (1,10-NDF) or the ortho-benzo[1,2-b:6,5-b']difuran-2,7-dione (1,8-BDF) chromophore in the main chain is described. The polymers P1 and P2' were prepared upon Suzuki coupling of either 3-(4-bromophenyl)-8-(3-bromo-4,5-dimethoxyphenyl)-naphtho[2,1-b:3,4-b']difuran-2,9-dione (M1) or 3,6-bis(4-bromophenyl)-1,2,3,5,6,7-hexahydrobenzo[1,2-b:6,5-b']difuran-2,7-dione (M2') and 2,2-(9,9-dioctyl-9H-fluorene-2,7-diyl-)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (M3), respectively. P2' was subsequently converted into the oxidized form P2 upon reaction with nitrobenzene. Optical and electrochemical properties of P1 and P2 are described and compared with the properties of previously prepared polymer P3, which was synthesized upon Suzuki coupling of symmetrical 3,8-bis(4-bromophenyl)naphtho[2,1-b:3,4-b']difuran-2,9-dione (M4) and M3. While the NDF-based polymers P1 and P3 exhibit absorption maxima around 480 nm, the BDF-based polymer P2 shows a maximum at 555 nm. Quantum chemical studies by the density functional theory method show that the BDF-based polymer is more planar than the polymers based on NDF. The excitation of the polymers causes a strong electron transfer from the backbone to the NDF/BDF core units. 1,10-NDF-based polymers exhibit excellent photostability in UV-light, while the 1,8-BDF-based polymer is less stable, if irradiated with a 200 W Hg lamp. All polymers exhibit low band gaps of 1.31 to 1.66 eV.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Zhang, HaichangUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Zhang, JunUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Tieke, BerndUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-451246
DOI: 10.1039/c3py01101a
Journal or Publication Title: Polym. Chem.
Volume: 5
Number: 2
Page Range: S. 646 - 653
Date: 2014
Publisher: ROYAL SOC CHEMISTRY
Place of Publication: CAMBRIDGE
ISSN: 1759-9962
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
CONJUGATED POLYMERS; ABSORPTION; REDMultiple languages
Polymer ScienceMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/45124

Downloads

Downloads per month over past year

Altmetric

Export

Actions (login required)

View Item View Item