Adaptable Overhanging Carboxylic Acid Porphyrins Towards Molecular Assemblies through Unusual Coordination Modes

Wael Barakat (1) , Ismail Hijazi (2) , Thierry Roisnel (1) , Vincent Dorcet (1) , Bernard Boitrel (1) , Stephane Le Gac (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LU - Lebanese University [Beirut]

A new family of strap porphyrins exhibiting out/in overhanging carboxylic acid stereoisomerism, has been synthesized and investigated for its coordination properties. Their 5,10 linkage allows a significant flexibility of the strap which exhibits various degrees of angulation relatively to the mean porphyrin plane, making the ligand adjustable to the metal it binds. Notably, in the case of Bi(III), a second sphere of coordination plays a crucial role for the side selective insertion of the large metal ion. As a result, inward and outward orientation of the overhanging carboxylic acid function can be tuned, which is of interest for supramolecular coordination assemblies.

Keywords: Hydrogen bonds; Coordination modes; Zinc; Bismuth; Conformation analysis

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Coordination chemistry

Wael Barakat, Ismail Hijazi, Thierry Roisnel, Vincent Dorcet, Bernard Boitrel, et al.. Adaptable Overhanging Carboxylic Acid Porphyrins Towards Molecular Assemblies through Unusual Coordination Modes. European Journal of Inorganic Chemistry, 2019, 2019 (25), pp.3005-3014. ⟨10.1002/ejic.201900539⟩. ⟨hal-02278396⟩