Issue 10, 2011

Modular synthesis of poly(perylene bisimides) using click chemistry: a comparative study

Abstract

A systematic study of the influence of the chemical substitution pattern of side chain polymers carrying perylene bisimide (PBI) pendants is presented. To achieve a high comparability, the modular approach of copper-catalyzed azidealkyne cycloaddition (CuAAC, “click” chemistry) was chosen to attach six differently substituted PBI azide moieties to a poly(propargyloxystyrene) backbone to obtain poly(perylene bisimides), PPBIs. The N, N′ substituted PPBIs differ structurally in two ways. On the one hand, the N-swallow-tail substituent was varied between hydrophilic oligoethyleneglycol and hydrophobic alkyl groups. On the other hand, the length of the N′-alkyl spacer, connecting PBI moiety and polymer backbone, was varied from (CH2)6 to (CH2)8 and to (CH2)11. The polymer analogous reactions between PBI-azides and poly(propargyloxystyrene) were monitored by 1H NMR and were found to be nearly quantitative in all cases. The resulting PPBIs exhibit Mn around 60 000 g mol−1 and narrow PDIs of 1.1. Structure–property relationships of all polymers were elucidated by studying their thermal behaviour using DSC and their structural properties with XRD measurements.

Graphical abstract: Modular synthesis of poly(perylene bisimides) using click chemistry: a comparative study

Supplementary files

Article information

Article type
Paper
Submitted
03 May 2011
Accepted
08 Jun 2011
First published
13 Jul 2011

Polym. Chem., 2011,2, 2213-2221

Modular synthesis of poly(perylene bisimides) using click chemistry: a comparative study

A. S. Lang and M. Thelakkat, Polym. Chem., 2011, 2, 2213 DOI: 10.1039/C1PY00191D

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