1. Three Isomeric Dioctyl Derivatives of 2,7-Dithienyl[1]benzo-thieno[3,2-b][1]benzothiophene: Synthesis, Optical, Thermal, and Semiconductor Properties.
- Author
-
Levkov LL, Surin NM, Borshchev OV, Titova YO, Dubinets NO, Svidchenko EA, Shaposhnik PA, Trul AA, Umarov AZ, Anokhin DV, Rosenthal M, Ivanov DA, Ivanov VV, and Ponomarenko SA
- Abstract
Organic semiconductor materials are interesting due to their application in various organic electronics devices. [1]benzothieno[3,2-b][1]benzothiophene (BTBT) is a widely used building block for the creation of such materials. In this work, three novel solution-processable regioisomeric derivatives of BTBT-2,7-bis(3-octylthiophene-2-yl)BTBT ( 1 ), 2,7-bis(4-octylthiophene-2-yl)BTBT ( 2 ), and 2,7-bis(5-octylthiophene-2-yl)BTBT ( 3 )-were synthesized and investigated. Their optoelectronic properties were characterized experimentally by ultraviolet-visible and fluorescence spectroscopy, time-resolved fluorimetry, and cyclic voltammetry and studied theoretically by Time-Dependent Density Functional Theory calculations. Their thermal properties were investigated by a thermogravimetric analysis, differential scanning calorimetry, polarizing optical microscopy, and in situ small-/wide-angle X-ray scattering measurements. It was shown that the introduction of alkyl substituents at different positions (3, 4, or 5) of thiophene moieties attached to a BTBT fragment significantly influences the optoelectronic properties, thermal stability, and phase behavior of the materials. Thin films of each compound were obtained by drop-casting, spin-coating and doctor blade techniques and used as active layers for organic field-effect transistors. All the OFETs exhibited p-channel characteristics under ambient conditions, while compound 3 showed the best electrical performance with a charge carrier mobility up to 1.1 cm
2 ·V-1 s-1 and current on/off ratio above 107 .- Published
- 2025
- Full Text
- View/download PDF