e-journal
Fused-Ring Pyrazine Derivatives for n-Type Field-Effect Transistors
ABSTRACT
Three new fused-ring pyrazine derivatives end-functionalized with trifluoromethylphenyl groups have been synthesized. The effect of a fused-ring pyrazine core on the thermal, electronic, optical, thin film morphology, and organic field-effect transistor (OFET) properties was investigated both experimentally and theoretically. Electrochemistry measurements and density functional theory calculations suggest that the pyrazine core plays a significant role in tuning the electron affinities of these compounds. The optical absorption and fluorescence properties are also sensitive to the pyrazine core. The OFET devices based on the fused-ring pyrazine compounds exhibit electron mobilities as high as ca. 0.03 cm2 V-1 s-1 under nitrogen, and their performance is sensitive to the pyrazine core. The larger pyrazine core leads to a lower LUMO level and lower reorganization energy, to more ordered thin film morphology with larger grain size, and finally to higher mobilities.
KEYWORDS: n-type organic semiconductor • field-effect transistor • fused-ring pyrazine • synthesis • density functional theory • structure-property relationship
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