C-3-symmetric chiral triaryltriazasumanenes were successfully prepared in good yields by Pd-catalyzed cross-coupling reactions of chiral tris(methylthio) triazasumanene with various arylboronic acids. These chiral triaryltriazasumanenes showed very stable bowl chirality without racemization at room temperature. Single-crystal X-ray crystallography of the p-(trifluoromethyl) phenyl derivative revealed the formation of unidirectional pi-pi stacking columns that were connected by F center dot center dot center dot F interactions unlike the non-columnar crystal packing of tris(methanesulfonyl) triazasumanene.