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Single crystals of thiophene-phenylene co-oligomers (TPCO) are promising optoelectronic materials for light-emitting devices as they combine efficient charge carrier transport and high luminescence. These electronic properties are controlled by the chemical structure of the molecules and their crystal packing; however, the structure-property relationships in TPCO single crystals have not yet been properly understood. Here, we study the impact of molecular end-groups (H, F, CH3, CF3, Si-(CH3)3, C-(CH3)3, O-CH3) on the structural and electronic properties of vapor-grown TPCO single crystals with the same phenylene-thiophene-thiophene-phenylene (PTTP) conjugated core using optical/atomic force microscopy, x-ray diffraction, DFT and other calculations, and field-effect transistor (FET) measurements.