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

Title data

Lang, Andreas ; Thelakkat, Mukundan:
Modular synthesis of poly(perylene bisimides) using click chemistry : a comparative study.
In: Polymer Chemistry. Vol. 2 (2011) . - pp. 2213-2221.
ISSN 1759-9954
DOI: https://doi.org/10.1039/c1py00191d

Project information

Project financing: Deutsche Forschungsgemeinschaft

Abstract in another language

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 azide-alkyne 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 60000 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.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I
Profile Fields
Profile Fields > Advanced Fields
Profile Fields > Advanced Fields > Polymer and Colloid Science
Graduate Schools
Graduate Schools > Bayreuth Graduate School of Mathematical and Natural Sciences (BayNAT)
Graduate Schools > Bayreuth Graduate School of Mathematical and Natural Sciences (BayNAT) > Photophysics of Synthetic and Biological Multichromophoric Systems
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professorship Applied Functional Polymers > Professorship Applied Functional Polymers - Univ.-Prof. Dr. Mukundan Thelakkat
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professorship Applied Functional Polymers
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 13 Apr 2016 08:20
Last Modified: 05 Apr 2018 13:42
URI: https://eref.uni-bayreuth.de/id/eprint/1218