Aggregation properties of soluble quinacridones in two and three dimensions

The aggregation properties of derivatives of linear trans-quinacridone, an archetypal pigment, have been explored in two and three dimensions. The sparse solubility of the parent quinacridone pigment in common organic solvents can be traced back to the formation of a network of hydrogen bonds. Introducing aliphatic substituents on specific positions of the quinacridone core leads to an increased solubility without hampering the formation of intermolecular hydrogen bonds. With UV-Vis absorption, steady-state fluorescence, and infrared spectroscopy, the aggregation behavior of these substituted quinacridone derivatives is studied. On the basis of these data, models are proposed for the aggregate structure in solution. In addition, the two-dimensional ordering on graphite of these compounds and N,N'-dialkylated analogues has been investigated with scanning tunneling microscopy. The comparison between the two-dimensional organization and the solution data allows one to identify the extent of intermolecular interactions involved in the aggregation process.