Self-Organization of Tetraazaporphyrin Derivatives in 2 and 3 Dimensions

Many applications of dyes, such as phthalocyanines (Pcs) and tetraazaporphyrins (TAPs), require specific supramolecular structures for the achievement of advanced properties. Most approaches towards nanostructured materials of Pcs and TAPs are based on their self-organizing properties that lead to many interesting properties but also highlighted some limitations. The work presented here describes new amphiphilic TAPs that form stable Langmuir and LB monolayers with a face-on orientation of the macrocycle and self-organize into columnar liquid crystaline structures. Both types of self-organized structures were successfully crosss-linked via cycloadditions of azide and acetylene groups with and without Cu catalyst. Surprisingly, the supramolecular structures of the self-organized structures were only marginally affected by the cross-linking processes.