Synthesis and ligand binding properties of triptycene-linked porphyrin arrays

Eimear Finnigan , Régis Rein (1) , Nathalie Solladié (1) , Katja Dahms , Daniel C.G. Götz , Gerhard Bringmann , Mathias Senge

1 LCC - Laboratoire de chimie de coordination

Multiporphyrin arrays are a complex class of molecules with numerous potential applications in energy transfer, photomedicine, and light harvesting. We have developed a facile/versatile route to a class of triptycene-linked porphyrin arrays via both Suzuki and Sonogashira cross-coupling methods, which makes use of the rigid three-pronged orientation of triptycene to construct trimeric porphyrin arrays linked either in the meso or β-position with various linker groups. In order to understand the properties of these potential antenna systems and probe their potential applications, the coordination behavior of zinc(II) derivatives with mono- and bidentate N-donor ligands was investigated. Depending on ligand concentration, both one- and two-point binding was observed with a bidentate ligand. Also/in addition, different cavity sizes, obtained by the use of different linker groups, resulted in differences in the binding properties of each trimeric system.

Mots clés: Porphyrins; Triptycenes; Suzuki coupling; Sonogashira coupling; Ligand binding; Antenna systems

Domaines: Chimie

Eimear Finnigan, Régis Rein, Nathalie Solladié, Katja Dahms, Daniel C.G. Götz, et al.. Synthesis and ligand binding properties of triptycene-linked porphyrin arrays. Tetrahedron, 2011, 67 (6), pp.1126-1134. ⟨10.1016/j.tet.2010.12.025⟩. ⟨hal-02361846⟩