•A series of new pyrene derivatives with chalcogen atoms as bridges were synthesized.•Thermal, optical and electrochemical properties of the pyrene derivatives were studied.•Single crystal structures and molecular packing were investigated.•The field effect transistor based on the semiconductor pyrene derivatives was constructed and characterized.•The microstructure of thin films was characterized by XRD and AFM.To explore how the different intermolecular non-covalent interactions synergistically affect the molecular packing and properties when they existed at the same molecules. A series of new pyrene derivatives with chalcogen atoms as bridges were designed and synthesized. The single crystal structures of the compounds revealed the significant effect of different intermolecular non-covalent interactions on the molecular packing. The thin film transistor devices were fabricated and exhibit high mobility over 0.04 cm2 V−1 s−1. The distinct difference of the OFETs performance suggests that the intermolecular non-covalent interactions have very important effect on gearing the molecular packing and properties.A series of new pyrene derivatives with chalcogen atoms as bridges were synthesized. The single crystal structures revealed the significant effect of different intermolecular noncovalent interactions on the molecular packing. The thin film transistor devices were fabricated and exhibit high mobility over 0.04 cm2 V−1 s−1.Download high-res image (198KB)Download full-size image

A novel two-dimensional (2D) starphene containing sulfur organic semiconductor material BTBTT was synthesized. The spectroscopy, electrochemistry and thermostability of the semiconductor material were investigated, and it was observed that the compound exhibits good stability. The BTBTT exhibits a strong aggregation tendency, forming long single-crystal nanowires, as evidenced by scanning electron microscopy (SEM) and transmission electron microscopy (TEM). The organic field-effect transistors (OFETs) devices were fabricated based on the thin films and single-crystal nanowires of BTBTT, respectively, which exhibit excellent FET performances with a high hole mobility of up to 0.56 cm2 V−1 s−1 with low threshold voltages.

A 2D condensed benzothiophene derivative TBTDBT was synthesized. The thermal, optical and electrochemical properties were investigated. The single crystalline microribbons were grown by solution drop-casting and physical vapor transport methods respectively. The field effect transistors based on TBTDBT microribbons were fabricated and a mobility up to 2.62 cm2 V−1 s−1 and an on–off ratio greater than 105 could be achieved.

•A novel thienoacene derivative C6-DBTTA is synthesized.•Thermal, optical and electrochemical properties of the C6-DBTTA were studied.•The field effect transistor based on the semiconductor C6-DBTTA was constructed and characterized.•The microstructure of thin films was characterized by XRD.•The morphology of thin films was characterized by AFM.A novel semiconductor material based on dialkylated thienoacene is designed and synthesized. The dihexyl-substituted dibenzotetrathienoacene derivative C6-DBTTA exhibits high stability which is evidenced by thermogravimetric analysis (TGA), UV–vis spectroscopy and electrochemistry. X-ray diffraction measurements of the vacuum-evaporated thin films show strong diffraction and indicate that the molecules are stacked nearly perpendicular to the substrate. AFM images reveal that the morphology of thin films depended on the deposition temperature. Thin film FETs devices based on C6-DBTTA were constructed and showed high mobility up to 0.48 cm2 V−1 s−1 and an on/off ratio over 107. These results suggest that this new dihexylated thienoacene is an important organic semiconductor for field effect transistors.A novel six fused rings thienoacene (C6-DBTTA) semiconductor material was synthesized. This new dihexyl-substituted thienoacene derivative exhibits high thermal and oxidation stability and its thin film FET devices exhibit a high mobility up to 0.48 cm2 V−1 s−1 as well as an on/off ratio over 107.

Three new heteropentacene derivatives based on bis(benzothieno)silole were synthesized. The XRD characterization reveals that the crystal structures of the heteropentacenes can be significantly influenced by the methyl substitution. The optical and electrochemical properties were investigated and the experimental results confirm that the silole motif lowers the LUMO level of the heteropentacenes. Preliminary results show that the insertion of silole ring systems into rigid heteropentacenes leads to an improved solubility and high fluorescence quantum yield up to 0.74 in solution, which indicates the potential of these new silole-containing compounds for photonic and photoelectric applications. The strong and sensitive fluorescence quenching behavior towards picric acid (PA) demonstrates that the silole-containing heteropentacene derivatives are also promising fluorescent sensor materials for detecting the nitro-containing explosives.

A 2D condensed benzothiophene derivative TBTDBT was synthesized. The thermal, optical and electrochemical properties were investigated. The single crystalline microribbons were grown by solution drop-casting and physical vapor transport methods respectively. The field effect transistors based on TBTDBT microribbons were fabricated and a mobility up to 2.62 cm2 V−1 s−1 and an on–off ratio greater than 105 could be achieved.

A novel two-dimensional (2D) starphene containing sulfur organic semiconductor material BTBTT was synthesized. The spectroscopy, electrochemistry and thermostability of the semiconductor material were investigated, and it was observed that the compound exhibits good stability. The BTBTT exhibits a strong aggregation tendency, forming long single-crystal nanowires, as evidenced by scanning electron microscopy (SEM) and transmission electron microscopy (TEM). The organic field-effect transistors (OFETs) devices were fabricated based on the thin films and single-crystal nanowires of BTBTT, respectively, which exhibit excellent FET performances with a high hole mobility of up to 0.56 cm2 V−1 s−1 with low threshold voltages.