Masahiro Nakano, I. Osaka, K. Takimiya
Jan 16, 2015
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Macromolecules
Abstract
A series of naphthodithiophene diimid (NDTI) based semiconducting polymers with various comonomer units, i.e., thienylenevinylene (TV), naphtho[1,2-b:5,6-b′]dithiophene (NDT), vinylene (V), benzo[c][1,2,5]thiadiazole (BTz), and naphtho[1,2-c:5,6-c′]bis[1,2,5]thiadiazole (NTz), were synthesized by Stille coupling or copper iodide-assisted Stille coupling using 2,7-dibromo-NDTI or 2,7-bis(trimethylstannyl)-NDTI, respectively. Their HOMO and LUMO energy levels were estimated by cyclic volttammetry and photoelectron spectroscopy. The HOMO energy levels of the NDTI-based polymers were strongly affected by the electronic nature of the comonomer units. In contrast, their LUMO energy levels were almost identical, likely owing to their localized LUMOs on the NDTI moiety. All the polymers showed air-stable electron transport in the field-effect transistors (FETs), thanks to their low-lying LUMO (∼−4.0 eV), as ambipolar (PNDTI-TV, -NDT, ∼0.082 cm2 V–1 s–1, μe = ∼0.029 cm2 V–1 s–1) or unipolar n-channel materials (PN...