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Synthesis of Poly(bisisoindigo) Using a Metal-Free Aldol Polymerization for Thin-Film Transistor Applications
journal contribution
posted on 2020-03-16, 15:30 authored by Anindya Ganguly, Keqiang He, Arthur D. Hendsbee, Maged Abdelsamie, Raymond N. Bennett, Yuning Li, Michael F. Toney, Timothy L. KellyTypical
syntheses of conjugated polymers rely heavily on organometallic
reagents and metal-catalyzed cross-coupling reactions. Here, we show
that an environmentally benign aldol polymerization can be used to
synthesize poly(bisisoindigo), an analog of polyisoindigo with a ring-fused
structural repeat unit. Owing to its extended conjugation length,
poly(bisisoindigo) absorbs across the UV/vis/NIR spectrum, with an
absorption tail that reaches 1000 nm. Due to the four electron-deficient
lactam units on each repeat unit, poly(bisoindigo) possesses a low-lying
LUMO, which lies at −3.94 eV relative to vacuum. Incorporation
of the ring-fused monomer unit also lowered the overall torsional
strain in the polymer backbone (relative to polyisoindigo), and the
polymer was successfully used in prototype unipolar n-channel organic
thin-film transistors.
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ring-fused monomer unitMetal-Free Aldol Polymerizationpolymer backboneelectron-deficient lactam unitsconjugation lengthpolyisoindigoprototype unipolar n-channelaldol polymerizationabsorption tailorganometallic reagentsLUMOUVmetal-catalyzed cross-coupling reactionsthin-film transistorstorsional strain1000 nmThin-Film Transistor Applications