Synthesis of N-doped chiral macrocycles by regioselective palladium-catalyzed arylation.

Abstract

A series of nitrogen (N)-doped macrocycles was successfully synthesized through palladium-catalyzed arylation. X-ray crystallographic characterization revealed the formation of isomeric products depending on the substituents on the N atoms. Notably, two intrinsically chiral macrocycles MC1 and MC3 with C ₁ symmetry were successfully obtained. These macrocycles exhibit exceptional photophysical properties, particularly remarkable high fluorescence quantum yields (Φ_F up to 0.69). Furthermore, enantiomeric resolution of inherent chiral MC1 was achieved using preparative chiral HPLC, enabling detailed investigation of its chiroptical behavior through circular dichroism and circularly polarized luminescence spectroscopy.