The scientific approach of the project is based on a combination of experimental and theoretical investigations. Project encompasses organic chemical synthesis, physico-chemical characterization of novel organic molecules, as well as quantum-chemical calculations and molecular modelling.The goal of the project is to investigate inherent physico-chemical properties of (poly)cyclic guanidines in which at least one nitrogen atom is embedded in heterocycle or attached to polycyclic structures. The objectives are: a) Synthesis of (poly)cyclic molecular systems possessing guanidine functionalities by employment of environmentally friendly synthetic methods (with the emphasize on cycloaddition reactions) and their spectroscopic and structural characterization; b) Mechanistic studies of reactions employed; c) Detailed insight into the fundamental molecular mechanisms how incorporation of guanidine moiety in cyclic structures mediates superbasicity properties; d) Development of model cyclic guanidine systems for anion sensing; e) Utilization of cyclic guanidine systems in development of base catalysis.The results of fundamental studies carried out within this project will enhance the understanding of physico-chemical factors governing superbasicity in cyclic systems and advance their design. Expected results will enable design and preparation of novel cyclic guanidine systems which could be applied in different research areas including anion sensing and homogeneous catalysis, synthesis of natural products and bioactive molecules.