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. 2018 May 1;10(5):487.
doi: 10.3390/polym10050487.

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

Anna Drewniak  1 , Mateusz D Tomczyk  2 , Lukasz Hanusek  3 , Anna Mielanczyk  4 , Krzysztof Walczak  5 , Pawel Nitschke  6 , Barbara Hajduk  7 , Przemyslaw Ledwon  8
Affiliations

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

Anna Drewniak et al. Polymers (Basel). .

Abstract

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.

Keywords: NDI; PDI; donor-acceptor; naphtalenediimide; perylenediimide; π-conjugated polymer.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Structures of studied polymers.
Scheme 2
Scheme 2
Synthesis path for polymer PCTB.
Scheme 3
Scheme 3
Synthesis path for polymer PCTB-PDI.
Scheme 4
Scheme 4
Synthesis path for polymer PCTB-NDI.
Figure 1
Figure 1
UV-Vis spectra of polymer solutions in CHCl3.
Figure 2
Figure 2
Cyclic voltammetry of polymer films spin coated on ITO electrode with ACN/Bu4NBF4 as supporting electrolyte.
Figure 3
Figure 3
Electron Paramagnetic Resonance spectroelectrochemistry: (a) first derivative of selected EPR signals in restricted range; (b) relative concentration of spins at different potential.
Figure 4
Figure 4
IV-curves of photovoltaic devices with PCTB-NDI or PCTB-PDI as one-component BHJ.
See this image and copyright information in PMC

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