Liquid Crystalline Tetraazaporphyrins

Tetraazaporphyrins (TAPs) are a unique type of macrocycle (cyclic macromolecules) which have a wide variety of uses in modern organic electronics. Specifically, they can be processed into thin films with particularly interesting sensory, optical and xerographic capabilities. Their nanostructure, especially in the liquid crystalline state, enables the formation of many different functional nanoarchitectures. However, the processing of TAPs is particularly challenging, especially due to their insolubility in most organic solvents. Moreover, the introduction of various side-chains to increase the solubility and of various metal centers in their central core, can drastically affect their self-assembly, orientations and reactivity. New strategies to effectively control the self-assembly of TAPs and rigidify the resulting nanoarchitecture are desirable to expand the utilization of these materials in organic electronics and to develop novel function nanomaterials. The topochemical photopolymerization of diynes towards polydiacetylenes, is a particularly attractive method to solidify and crosslinking TAPs in the liquid crystalline state. This presentation will focus on our recent efforts toward the design and synthesis of new soluble TAP macrocycles. Moreover, in order to covalently crosslink the TAPs in the liquid crystalline state and develop new well-defined nanostructure, the incorporation of aliphatic diyne-containing side-chains to the TAPs has been performed to enable the covalent crosslinking of the materials by photopolymerization. Finally, the potential of our new materials for various applications, including organic electronics and organic photovoltaics will be highlighted