C3-Symmetric Pyridine and Bipyridine Derivatives: Simple Preparation by Cyclocondensation and 2D Self-Assembly at a Solution–Graphite Interface

Abstract

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 fol-lowed by an acid-promoted cyclocondensation reaction converting the methyl ketone moiety into the central benzene ring of the target com-pounds. 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.