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NMRP versus "Click" Chemistry for the Synthesis of Semiconductor Polymers Carrying Pendant Perylene Bisimides

Title data

Lang, Andreas ; Neubig, Anne ; Sommer, Michael ; Thelakkat, Mukundan:
NMRP versus "Click" Chemistry for the Synthesis of Semiconductor Polymers Carrying Pendant Perylene Bisimides.
In: Macromolecules. Vol. 43 (2010) Issue 17 . - pp. 7001-7010.
ISSN 0024-9297
DOI: https://doi.org/10.1021/ma100708h

Project information

Project financing: Deutsche Forschungsgemeinschaft

Abstract in another language

The synthesis of well-defined polymers with pendant perylene bisimide (PBI) groups by a combination of nitroxide-mediated radical polymerization (NMRP) of trimethylsilyl propargyl acrylate followed by copper-catalyzed azide−alkyne cycloaddition (CuAAC, "click" chemistry) is described. The kinetics of NMRP of trimethylsilyl propargyl acrylate polymerization was monitored by 1H NMR and size exclusion chromatography (SEC). Almost quantitative conversion in the "click" reaction with an azide functionalized PBI derivative was proven by FTIR and 1H NMR analysis. Thus, semiconductor polymers carrying PBI pendant groups with Mn up to 15800 g·mol−1 and polydispersity indices as good as 1.16 were obtained by this route. These polymers were compared with poly(perylene bisimide acrylate)s, PPerAcr(CH2)11, and PPerAcr(CH2)6, which were synthesized by direct NMRP of PBI acrylates. These samples do not carry any triazol unit and they differ in their spacer length connecting the PBI unit to the main chain. All polymers were comparatively studied by SEC, thermogravimetry, differential scanning calorimetry, polarization microscopy, UV/vis spectroscopy, and photoluminescence measurements. The crystalline structure of the polymers was analyzed by X-ray diffraction. Inductively coupled plasma mass spectrometry analysis confirmed that copper content in the "click" polymer could be reduced down to 126 ppm (w/w).

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
Research Institutions
Research Institutions > Collaborative Research Centers, Research Unit
Research Institutions > Collaborative Research Centers, Research Unit > SFB 481 Komplexe Makromolekül- und Hybridsysteme in inneren und äußeren Feldern
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: 14 Apr 2016 06:42
Last Modified: 05 Apr 2018 13:43
URI: https://eref.uni-bayreuth.de/id/eprint/1256