Synthesis of benzotrifuran and benzotripyrrole derivatives and molecular orientations on the surface and in the solid state.

We developed a concise synthetic method for benzotrifurans and benzotripyrroles from 1,3,5-triethynyl-2,4,6-trifluorobenzenes by one-pot reactions in good to excellent yield. By investigating 2-D and 3-D structures of a variety of benzotrifuran and benzotripyrrole derivatives using scanning tunneling microscopy (STM) and single-crystal X-ray diffraction techniques, we found both similarities and dissimilarities. We also found that diverse molecular 3-D orientations were derived in their single crystals according to substituents on the molecules and that the emission properties in the solid state are dependent on their packing manners.