OFET performance of low-symmetric 5-TIPS-ethynyl-15-TMS-ethynyl-tetrabenzoporphyrins in the single crystal states

To achieve the high charge carrier mobility of small molecular organic semiconductors, a molecular design strategy for controlling the packing structure of two-dimensional (2D) [Formula: see text]-extended organic semiconductors in single crystal is essential. Although tetrabenzoporphyrin (BP) is one of the promising organic semiconductors, the control of the packing structure is still challenging. To improve the low solubility of 5,15-bis(trimethylsilylethynyl)-tetrabenzoporphyrin (TMS-BP) and the crystal polymorph of 5,15-bis(triisopropylsilylethynyl)-tetrabenzoporphyrin (TIPS-BP), 5-triisopropylsilylethynyl-15-trimethylsilylethynyl-tetrabenzoporphyrin (TIPS-TMS-BP) with different substituents at meso-positions was synthesized. TIPS-TMS-BP gave a herringbone structure of antiparallel slipped-stack dimers in single crystals. The single crystal field effect transistors exhibit a high hole mobility of 1.65 cm 2 V[Formula: see text] s[Formula: see text] in parallel to [Formula: see text]–[Formula: see text] stacking direction and moderate 0.37 cm 2 V[Formula: see text] s[Formula: see text] in perpendicular to [Formula: see text]–[Formula: see text] stacking direction.