This highlight review provides an overview of recent developments in the chemistry of pyridyl-functionalized lambda(3)sigma(2)-phosphinines and 3H-1,2,3,4-triazaphospholes. The access to novel chelating, low-coordinate phosphorus heterocycles can lead to a much broader scope for potential applications. New developments in areas such as homogeneous catalysis, molecular materials, and supramolecular chemistry can consequently be foreseen in the near future.