An Investigation of Naphthalenediimides as Central Building Blocks in Model Compounds for Scanning Tunneling Microscope Induced Light Emission Experiments and Förster Resonance Energy Transfer Studies

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Scanning tunnelling microscopy (STM) is a powerful technique to observe surfaces at the atomiclevel. The resolution of this STM technique is good enough to study the electronic properties of singlemolecules adsorbed onto metallic substrates. An important step towards controllable single moleculartechnologies is the determination of how the molecule-substrate interaction changes the localmolecular electronic structure. Since this electronic structure of molecules is strongly perturbed by theelectrons of the underlying metallic substrate, an electronic decoupling of the molecules from themetal surface is required to isolate the electronic properties of an individual molecule.Förster resonance energy transfer (FRET) has found many applications in different fields of science, because it allows the determination of the distance between two chromophores in the 1-10 nm range.In addition to other factors, this energy transfer is also dependent on the relative orientation of donorand acceptor chromophores to each other.This thesis describes the design, synthesis and investigations of model compounds for:1). STM induced light emission experiments from single molecules and2). for FRET studies.Chapter 1 provides an introduction to cyclophanes, energy transfer and scanning tunnellingmicroscopy.Chapter 2 gives a description of the aims of this work, which is split into the synthesis of cyclophanesfor STM induced luminescence investigations and FRET studies. The later is complemented by thesynthesis of a linear NDI system.Chapter 3 describes the design, synthesis and characterisation of all model compounds. In the first halfSTM investigations are presented and the electronic structure of two cyclophanes and complexationstudies of the crown ether model compound are discussed. In the second half a modular synthetic routeto asymmetric N, N'-naphthalenediimides is presented for FRET studies.Chapter 4 gives a summary of this thesis and presents a short outlook.Chapter 5 provides the synthesis and characterisation of all the compounds listed in this thesis andexperimental details for STM investigations.