10.1021/acs.macromol.5b02659.s001
Christian
J. Mueller
Christian
J.
Mueller
Tobias Klein
Tobias
Klein
Eliot Gann
Eliot
Gann
Christopher R. McNeill
Christopher R.
McNeill
Mukundan Thelakkat
Mukundan
Thelakkat
Azido-Functionalized Thiophene as a Versatile Building
Block To Cross-Link Low-Bandgap Polymers
American Chemical Society
2016
Solvent resistivity
absorption
electrochemical properties
UV illumination
polymerization techniques
Versatile Building Block
polymer films
azide functionality
HOMO
Thermal stability
model blend system
butyric acid methyl ester
field effect transistors
azide groups
photoluminescence measurements
PC 70 BM
2016-05-03 13:59:39
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Azido_Functionalized_Thiophene_as_a_Versatile_Building_Block_To_Cross_Link_Low_Bandgap_Polymers/3208015
We unveil a concept
for the design of cross-linkable semiconducting
polymers that is based on a modular tercopolymerization which stands
out by its low synthetic effort, easy accessibility, and its broad
range of applications. 3-(6-Azidohexyl)thiophene was used as a comonomer
in the synthesis of a variety of low-bandgap copolymers using different
polymerization techniques such as Suzuki–Miyaura cross-coupling
and Stille cross-coupling. We show that when only a small amount (5–10
mol %) of azide groups is introduced into the polymers, the impact
on absorption and electrochemical properties (HOMO/LUMO values) is
negligible. The small amount of azide functionality is however enough
to obtain polymers that can easily be cross-linked by UV illumination.
Thermal stability of the solid state packing and alignment is studied
in neat polymer thin films as well as in blends with [6,6]-phenyl-C<sub>71</sub>-butyric acid methyl ester (PC<sub>70</sub>BM) as a relevant
model blend system. Solvent resistivity of these polymer films is
investigated by absorption and photoluminescence measurements. It
is finally shown in organic field effect transistors that the introduction
of 10% azide-functionalized monomer does not considerably influence
hole transport mobility (0.20–0.45 cm<sup>2</sup> V<sup>–1</sup> s<sup>–1</sup>).