Twisted naphthyl ethynes for molecular conductance measurements

Molecular electronics investigates the use of molecules in electronic devices. An important question is how the chemical structure influences the charge transport properties and how the molecules are integrated into an electrical circuit. From a chemical point of view, this can be addressed by the design and synthesis of molecules with well-defined features that are able to perform electronic functions. In the first part, we review the field of molecular electronics and especially the correlation between the molecular conformation and the optoelectronic properties in diphenyl acetylene derivatives.
This thesis is focused on the design and synthesis of dinaphthyl acetylene with controlled torsion angles. A linker of varying length connects the naphthyl moieties, thereby restricting the rotational freedom. This will partially disrupting the conjugation across the molecule. We aim to quantify this effect in conductance experiments and correlate it with the torsion angle a.
Our synthetic efforts involved linking the naphthalenes via aryl alkyl ethers and benzyl ethers. In the former case, our attempts to introduce a linker resulted in a cyclisation of hydroxy groups and alkynes. In the latter case, we obtained no definitive results, as precursors are not readily available. Nevertheless, these findings will guide future research towards finding a feasible approach and ultimately contribute towards better understanding of conformation/conductance of organic molecules.