The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer Properties

The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer Properties

The presented study describes the method for the synthesis and characterization of a new class of conjugated copolymers containing a perylenediimide (PDI) and naphthalene diimide (NDI) side groups. The main conjugated backbone is a donor-acceptor polymer poly[3,6-carbazole-alt-5,5-(4′,7′-di-2-thieny...

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Main Authors: Anna Drewniak, Mateusz D. Tomczyk, Lukasz Hanusek, Anna Mielanczyk, Krzysztof Walczak, Pawel Nitschke, Barbara Hajduk, Przemyslaw Ledwon
Format: Article
Language:English
Published: MDPI AG 2018-05-01
Series:Polymers
Subjects:
π-conjugated polymer
donor-acceptor
perylenediimide
PDI
naphtalenediimide
NDI
Online Access:http://www.mdpi.com/2073-4360/10/5/487
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spelling doaj-36022fe1c9be4904baca2864fa5c4b672020-11-24T23:21:14ZengMDPI AGPolymers2073-43602018-05-0110548710.3390/polym10050487polym10050487The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer PropertiesAnna Drewniak0Mateusz D. Tomczyk1Lukasz Hanusek2Anna Mielanczyk3Krzysztof Walczak4Pawel Nitschke5Barbara Hajduk6Przemyslaw Ledwon7Faculty of Chemistry, Silesian University of Technology, Strzody 9, 44-100 Gliwice, PolandFaculty of Chemistry, Silesian University of Technology, Strzody 9, 44-100 Gliwice, PolandFaculty of Chemistry, Silesian University of Technology, Strzody 9, 44-100 Gliwice, PolandFaculty of Chemistry, Silesian University of Technology, Strzody 9, 44-100 Gliwice, PolandFaculty of Chemistry, Silesian University of Technology, Strzody 9, 44-100 Gliwice, PolandCentre of Polymer and Carbon Materials, Polish Academy of Sciences, Curie-Sklodowskiej 34, 41-819 Zabrze, PolandCentre of Polymer and Carbon Materials, Polish Academy of Sciences, Curie-Sklodowskiej 34, 41-819 Zabrze, PolandFaculty of Chemistry, Silesian University of Technology, Strzody 9, 44-100 Gliwice, PolandThe presented study describes the method for the synthesis and characterization of a new class of conjugated copolymers containing a perylenediimide (PDI) and naphthalene diimide (NDI) side groups. The main conjugated backbone is a donor-acceptor polymer poly[3,6-carbazole-alt-5,5-(4′,7′-di-2-thienyl-2′,1′,3′-benzothiadiazole)] containing thiophene and carbazole as donor units and benzothiadiazole as an acceptor unit. The presented compounds were synthesized in a multistep synthesis. The polymerization was carried out by Suzuki or Stille coupling reaction. Redox properties of the studied polymers were tested in different conditions. Electrochemical investigation revealed independent reduction of the main polymer chain and diimide side groups. UV-Vis spectroscopy revealed the overlap of two absorption spectra. The difference between the electron affinity of the polymer main chain and that of the diimides estimated electrochemically is approximately 0.3 eV.http://www.mdpi.com/2073-4360/10/5/487π-conjugated polymerdonor-acceptorperylenediimidePDInaphtalenediimideNDI
collection DOAJ
language English
format Article
sources DOAJ
author Anna Drewniak
Mateusz D. Tomczyk
Lukasz Hanusek
Anna Mielanczyk
Krzysztof Walczak
Pawel Nitschke
Barbara Hajduk
Przemyslaw Ledwon
spellingShingle Anna Drewniak
Mateusz D. Tomczyk
Lukasz Hanusek
Anna Mielanczyk
Krzysztof Walczak
Pawel Nitschke
Barbara Hajduk
Przemyslaw Ledwon
The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer Properties
Polymers
π-conjugated polymer
donor-acceptor
perylenediimide
PDI
naphtalenediimide
NDI
author_facet Anna Drewniak
Mateusz D. Tomczyk
Lukasz Hanusek
Anna Mielanczyk
Krzysztof Walczak
Pawel Nitschke
Barbara Hajduk
Przemyslaw Ledwon
author_sort Anna Drewniak
title The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer Properties
title_short The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer Properties
title_full The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer Properties
title_fullStr The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer Properties
title_full_unstemmed The Effect of Aromatic Diimide Side Groups on the π-Conjugated Polymer Properties
title_sort effect of aromatic diimide side groups on the π-conjugated polymer properties
publisher MDPI AG
series Polymers
issn 2073-4360
publishDate 2018-05-01
description The presented study describes the method for the synthesis and characterization of a new class of conjugated copolymers containing a perylenediimide (PDI) and naphthalene diimide (NDI) side groups. The main conjugated backbone is a donor-acceptor polymer poly[3,6-carbazole-alt-5,5-(4′,7′-di-2-thienyl-2′,1′,3′-benzothiadiazole)] containing thiophene and carbazole as donor units and benzothiadiazole as an acceptor unit. The presented compounds were synthesized in a multistep synthesis. The polymerization was carried out by Suzuki or Stille coupling reaction. Redox properties of the studied polymers were tested in different conditions. Electrochemical investigation revealed independent reduction of the main polymer chain and diimide side groups. UV-Vis spectroscopy revealed the overlap of two absorption spectra. The difference between the electron affinity of the polymer main chain and that of the diimides estimated electrochemically is approximately 0.3 eV.
topic π-conjugated polymer
donor-acceptor
perylenediimide
PDI
naphtalenediimide
NDI
url http://www.mdpi.com/2073-4360/10/5/487
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