N-Confused Hexapyrrolic Phlorinoid with NIR Absorption: Synthesis, Fusion, Oxidation, and Copper(II) Coordination.

An N-confused hexapyrrolic phlorinoid and its isomer N-fused hexapyrrolic phlorinoid were synthesized through [4 + 2] condensation. Both and can be readily transformed into N-confused hexapyrrolic phlorinone under aerobic conditions. Coordination of with Cu(acac) afforded two different mono-Cu(II) complexes and with CNNN and ONNN coordination environments, respectively.

N-Confused Phlorin-Prodigiosin Chimera: meso-Aryl Oxidation and π-Extension Triggered by Peripheral Coordination.

An N-confused phlorin isomer bearing a dipyrrin moiety at the α-position of the confused pyrrole ring (1) was synthesized. Pd and B coordination at the peripheral prodigiosin-like moiety of 1 afforded the corresponding complexes 2 and 3. Reflux of 2 in triethylamine (TEA) converted the meso-phenyl into the Pd -coordinating phenoxy group to afford 4.