This work aimed to develop novel molecular tweezers and to study the interactions involved in their binding with IT-electronically complementary receptors in solution and in the solid state. The tweezers were then tested as "reader" molecules for information-bearing copolymers. In the development of novel tweezer-molecules, this thesis highlights the importance of the choice of the spacer-unit. In some cases the nature of the spacer prevented binding altogether; while in others it gave new properties to the tweezers such as responsiveness to external stimuli. In more detail, novel pH-sensitive tweezers showed markedly different binding activities and fluorescent properties in various pH environments. For the determination of the binding constant, a new 1H-NMR-based method involving the dilution of a fixed-ratio solution was developed. This method was implemented for strongly binding tweezer-macrocycle complexes, as titration methods proved incompatible with such systems. A new kind of tweezer-molecule was developed by covalent inclusion of a Pd centre in a pyrene-armed tweezer-molecule. This metal centre enhanced the complexation strength of nitrile- and heterocycle-based ligands via a synergistic mechanism of binding in which both IT-IT stacking and Pd-coordination occur. The strong binding ability of t his new class of receptors provides opportunities for binding studies of complementary Pt-complexes, new information-bearing systems, and bio-receptors. Model compounds for a new class of copolyimide have been synthesized and their binding properties investigated. These copolymers have shown information-bearing properties. The interactions between model compounds for the tweezer-copolyimide systems were investigated at the metal/vacuum interface. The intermolecular interactions of macrocycles were explored as well as t heir interactions with Au{111} surface. The pie-pie stacking interactions of pyromellitic moieties and pyrene derivatives were studied on Cu{ll0}. These studies showed the ability of these molecules to arrange in ordered superstructures and demonstrated the existence of IT-IT stacking interactions at the solid/vacuum interface.