An Unsymmetrical 5,15-Disubstituted Tetrabenzoporphyrin: Effect of Molecular Symmetry on the Packing Structure and Charge Transporting Property

Molecular design strategy to control the crystal structure of two-dimensional (2D) pi-extended organic semiconductors has not been intensively explored. We synthesized an unsymmetric tetrabenzoporphyrin derivative (TIPS-Ph-BP) to demonstrate the effect of molecular symmetry on crystal packing. TIPS-Ph-BP formed an antiparallel slipped pi-stacking and 2D herringbone-like structure. An unsymmetric structure would make 2D pi-stacking more stable than a one-dimensional (1D) columnar structure to counteract steric and electronic imbalance in the crystal. As a result, TIPS-Ph-BP achieved the high hole mobility of 0.71 cm(2) V-1 s(-1).

Automated summary

This study demonstrates the impact of molecular symmetry on crystal packing using an unsymmetric molecule. The unsymmetric structure promotes the stability of 2D π-stacking and leads to high hole mobility.