Two-dimensional (2D) polymers attract considerable attention in different fields of basic and applied science. In this work, the synthesizability and properties of the 2D covalently stabilized monolayers built up of different monomeric subunits bearing 3, 4, and 6 photoreactive chalcone functionalities have been investigated. The self-assembled monolayers of the monomers have been polymerized under the UV-irradiation conditions on a Langmuir-Blodgett trough at the air/water interface. A trifunctional phloroglucinol-cored monomer formed mechanically poorly stable 2D covalent monolayers. On the contrary, the covalent monolayer films of calix[4]- and calix[6] arene based monomers bearing 4 chalcone groups each were mechanically stable enough to be span over 19 x 19 mm-sized holes of copper grids. Hexafunctionalized calix[6] arene failed to form stable monolayers at the air/water interface. The films have been transferred on different substrates and investigated by ellipsometry, optical microscopy, TEM, and AFM revealing details of their thickness, stability, and morphology. (C) 2015 Elsevier Ltd. All rights reserved.