The efficient preparation of four C3-symmetric (star-shaped) pyridine and bipyridine derivatives is reported. The key steps are Suzuki couplings of 4-pyridyl nonaflates with 4-acetyl-phenylboronic acid followed by an acid-promoted cyclocondensation reaction converting the methyl ketone moiety into the central benzene ring of the target compounds. Based on STM studies at a graphite–solution interface the two-dimensional arrangements of the compounds are discussed, showing the influence of the pyridine substitution pattern.