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

Matthias Grübel; Simon Meister; Ulrich Schulze; Konstantinos N. Raftopoulos; Franziska Baumer; Christine M. Papadakis; Tom Nilges; Bernhard Rieger

doi:10.1002/macp.201500289

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

Matthias Grübel, Simon Meister, Ulrich Schulze, Konstantinos N. Raftopoulos, Franziska Baumer, Christine M. Papadakis, Tom Nilges, Bernhard Rieger

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	59-71
Number of pages	13
Journal	Macromolecular Chemistry and Physics
Volume	217
Issue number	1
DOIs	https://doi.org/10.1002/macp.201500289
State	Published - 1 Jan 2016

Keywords

block copolymers
hydrogen bonds
oligothiophenes
polysiloxanes
thermoplastics

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10.1002/macp.201500289

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title = "Synthesis of Diisocyanate-Containing Thiophenes and Their Use in PDMS-Based Segmented Polymers",

abstract = "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.",

keywords = "block copolymers, hydrogen bonds, oligothiophenes, polysiloxanes, thermoplastics",

author = "Matthias Gr{\"u}bel and Simon Meister and Ulrich Schulze and Raftopoulos, {Konstantinos N.} and Franziska Baumer and Papadakis, {Christine M.} and Tom Nilges and Bernhard Rieger",

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year = "2016",

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doi = "10.1002/macp.201500289",

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T1 - Synthesis of Diisocyanate-Containing Thiophenes and Their Use in PDMS-Based Segmented Polymers

AU - Grübel, Matthias

AU - Meister, Simon

AU - Schulze, Ulrich

AU - Raftopoulos, Konstantinos N.

AU - Baumer, Franziska

AU - Papadakis, Christine M.

AU - Nilges, Tom

AU - Rieger, Bernhard

PY - 2016/1/1

Y1 - 2016/1/1

N2 - 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.

AB - 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.

KW - block copolymers

KW - hydrogen bonds

KW - oligothiophenes

KW - polysiloxanes

KW - thermoplastics

UR - http://www.scopus.com/inward/record.url?scp=84956613135&partnerID=8YFLogxK

U2 - 10.1002/macp.201500289

DO - 10.1002/macp.201500289

M3 - Article

AN - SCOPUS:84956613135

SN - 1022-1352

VL - 217

SP - 59

EP - 71

JO - Macromolecular Chemistry and Physics

JF - Macromolecular Chemistry and Physics

IS - 1

ER -

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

Abstract

Keywords

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