Synthesis of Diisocyanate-Containing Thiophenes and Their Use in PDMS-Based Segmented Polymers

A synthesis route to siloxane‐based thermoplastic elastomers (TPE) with functional hard blocks is described. The photophysical functionality is provided by oligothiophenes, namely terthiophene and bithiophene. Polyaddition of isocyanate‐bearing thiophenes and amine‐terminated siloxanes yields polyme...

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Bibliographic Details
Published in:Macromolecular chemistry and physics 2016-01, Vol.217 (1), p.59-71
Main Authors: Grübel, Matthias, Meister, Simon, Schulze, Ulrich, Raftopoulos, Konstantinos N., Baumer, Franziska, Papadakis, Christine M., Nilges, Tom, Rieger, Bernhard
Format: Article
Language:English
Subjects:
Bearing
block copolymers
Bonding strength
Carrier mobility
Chemical synthesis
Current carriers
Diffraction
Doppler effect
Elastomers
Emission
Fluorescence
Hydrogen bonds
oligothiophenes
Phase separation
Phase shift
Polymer films
Polymerization
Polymers
polysiloxanes
Red shift
Scattering
Segments
Siloxanes
Stacking
Synthesis
Thermoplastic elastomers
thermoplastics
Thiophenes
Tuning
X-ray diffraction
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Summary:A synthesis route to siloxane‐based thermoplastic elastomers (TPE) with functional hard blocks is described. The photophysical functionality is provided by oligothiophenes, namely terthiophene and bithiophene. Polyaddition of isocyanate‐bearing thiophenes and amine‐terminated siloxanes yields polymers incorporating a bisurea structure motive. Phase separation and strong hydrogen bonds provide ordering of the thiophenes, which is shown by wide‐angle X‐ray scattering (WAXS) and X‐ray powder diffraction (XRD). Fluorescence measurements reveal a strong red shift of emission of polymer films compared with polymer solutions, thus confirming the existence of hard block segments with an enhanced π system and higher charge–carrier mobility. Tuning of the optical band gap by different polymer compositions and various post polymerization treatments is demonstrated. Stacking of thiophene units within siloxane‐based polymers is supported by hydrogen bonds of urea groups. A phase separation is presented. Because of the stacking the fluorescence of the polymer materials is shifted to higher wavelengths. This effect can be used to analyze microcrystals in polymers.
ISSN:1022-1352
1521-3935
DOI:10.1002/macp.201500289