Effect of Chirality on the Binding of Viologen Guests in Porphyrin Macrocycles.

As part of a project aimed at the development of chiral processive catalysts that can write information on a polymer chain we describe the synthesis of two optically active porphyrin macrocycles, which are prepared in 3 steps from an achiral precursor compound. Fluorescence and H-NMR studies show that one of the macrocycles displays selectivity in the binding of chiral viologen guest molecules.

Directional threading of a chiral porphyrin cage compound onto viologen guests.

We report the face-selective threading of a chiral porphyrin cage compound onto viologen guests that are provided on both ends with substituents of different sizes. Depending on the types of terminal groups on the guest the cage compound orients itself in one of two possible directions.

Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration.

Nitration of tetraphenylporphyrin cage compound 1, at -40 °C, leads to the regioselective formation of the chiral mononitro compound 2 (75% isolated yield) and, at -30 °C, to the achiral syn-dinitro-derivative 3 and the chiral anti-dinitro derivative 4 in a diastereomeric ratio of 5:2, which were separated by chromatography (46 and 20% yields, respectively). The structures of the compounds were confirmed by X-ray crystallography.