The hydrogen bond: actor and stage in the theater of chemistry

Hydrogen bond plays a key role in a wide range of inorganic, organic, as well as biological systems. The understanding on how the chemical environment can affect this kind of interaction is crucial to predict its binding strength, and consequently the robustness and the dynamic properties of many supramolecular systems. Both in nature and in artificial system hydrogen bonding offers a plethora of possible assembling and arrangement between molecules. In this thesis, a theoretical approach was adopted to spotlight the intimate nature of hydrogen interactions in two unprecedented chemical H-bonded architecture: 1) an AA-DD pattern in a amine-borane azacrown involving a double dihydrogen interaction; 2) a BODIPY dyad generated by two complementary chromophores directly bearing in meso position an acceptor-donor-acceptor (A-D-A) and a donor-acceptor-donor (D-A-D) frontier geometry. Both cases were computationally treated by means density functional theory (DFT) in order to highlight hydrogen bond strengths, directionality and function-structure relationship.