This book provides an overview in recent progress in the field of synthesis and interactions of π-conjugated DNA binders through Click chemistry. The synbook of alkyne- and azide substituted oligoheteroaromatic compounds, were designed to be used as building blocks for Click reactions. The Pd-catalysed cross-coupling of azide-substituted building blocks to form oligoheteroaromatics is also described. The characterisation of the new π-conjugated molecules utilising Click chemistry between alkyne- and azide-substituted compounds leading to a series of structurally-varied di- and tricationic oligoheteroaromatic putative DNA binders. The DNA-binding studies for the di- and tricationic oligoheteroaromatic compounds using a variety of biophysical techniques to quantify DNA binding and elucidate binding modes. Finally, the overall conclusions of the study, including future studies and applications are presented.