π-extended "earring" porphyrins with multiple cavities and near-infrared absorption

β,β-tripyrrin-bridged earring porphyrins were synthesized through Suzuki-Miyaura cross coupling reactions. These porphyrinoids have multiple cavities and can accommodate two or three metal ions per molecule. The structures of the porphyrins have been elucidated by x-ray diffraction analysis, and feature curved π planes. The electronic spectra of the porphyrins exhibit near-infrared (NIR) absorptions and metal insertion leads to red-shifted and intensified absorption features. Electrochemical analysis and transient absorption measurements indicated that the porphyrins exhibit effective electronic communication between their central and peripheral moieties. Porphyrins with ears: β,β-Tripyrrin-bridged "earring" porphyrins were synthesized by Suzuki-Miyaura cross coupling reactions. These compounds have multiple cavities that can complex up to three metal ions. The porphyrin structures feature curved π planes, and their electronic spectra show near-infrared (NIR) absorptions. Metal insertion leads to red-shifted and intensified near-infrared absorption features.