%0 Journal Article
%A Mueller, Christian
J.
%A Klein, Tobias
%A Gann, Eliot
%A McNeill, Christopher R.
%A Thelakkat, Mukundan
%D 2016
%T Azido-Functionalized Thiophene as a Versatile Building
Block To Cross-Link Low-Bandgap Polymers
%U https://acs.figshare.com/articles/journal_contribution/Azido_Functionalized_Thiophene_as_a_Versatile_Building_Block_To_Cross_Link_Low_Bandgap_Polymers/3208015
%R 10.1021/acs.macromol.5b02659.s001
%2 https://acs.figshare.com/ndownloader/files/5037151
%K Solvent resistivity
%K absorption
%K electrochemical properties
%K UV illumination
%K polymerization techniques
%K Versatile Building Block
%K polymer films
%K azide functionality
%K HOMO
%K Thermal stability
%K model blend system
%K butyric acid methyl ester
%K field effect transistors
%K azide groups
%K photoluminescence measurements
%K PC 70 BM
%X 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-C71-butyric acid methyl ester (PC70BM) 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 cm2 V–1 s–1).
%I ACS Publications