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Synthesis and Aggregation Behavior of a Glycolated Naphthalene Diimide Bithiophene Copolymer for Application in Low-Level n‑Doped Organic Thermoelectrics
journal contribution
posted on 2020-07-01, 21:34 authored by Young-hun Shin, Hartmut Komber, Davide Caiola, Marco Cassinelli, Hengda Sun, Dominik Stegerer, Marcel Schreiter, Kilian Horatz, Franziska Lissel, Xuechen Jiao, Christopher R. McNeill, Simone Cimò, Chiara Bertarelli, Simone Fabiano, Mario Caironi, Michael SommerThe synthesis of
a naphthalene diimide bithiophene copolymer P(EO-NDIT2)
with branched, base-stable, and purely ether-based side chains is
presented. Stille polycondensation leads to high molecular weights
that are limited by methyl transfer and eventually T2 homocouplings.
While extensive solution aggregation hampers molecular weight determination
by conventional methods, NMR spectroscopy allows identification of
both T2- (H and methyl) and NDI-related (methyl) end groups, enabling
the determination of absolute number average molecular weights larger
than Mn,NMR ∼100 kg/mol. Solvent-
and temperature-dependent aggregation in solution is investigated
by NMR and UV–vis spectroscopy. These results are used for
solution doping of P(EO-NDIT2) with N-benzimidazole-based n-dopants.
Spin coating from heated chlorobenzene solutions and using 4-(2,3-dihydro-1,3-dimethyl-1H-benzoimidazol-2-yl)-N,N-diisopropylaniline (N-DiPrBI) as the dopant leads to homogeneous
films with highest conductivities up to 10–2 S/cm.
Generally, N-DiPrBI concentrations as low as ∼5 wt % are sufficient
to increase conductivity by orders of magnitude. Strikingly, maximum
power factors up to 0.11 μW/mK2, although limited
by conductivity, are achieved for the highest molar mass sample at
a low dopant concentration of 2 wt % N-DiPrBI only.
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Keywords
ether-based side chainsGlycolated Naphthalene Diimide Bith...NMR spectroscopypower factorsweight determinationsolution dopingmolar mass samplewtUVchlorobenzene solutionsdopant concentrationAggregation BehaviorN-benzimidazole-based n-dopantsincrease conductivityT 2-Spin coatingmethyl transferStille polycondensationtemperature-dependent aggregationT 2 homocouplingssolution aggregationend groupsN-DiPrBI concentrationsbenzoimidazol -2-yl N
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