Thermally Induced Synthesis of Anthracene-, Pyrene- and Naphthalene-Fused Porphyrins

The synthesis of pi-extended porphyrins containing anthracenyl moieties still represents an important challenge. Here, we report on the synthesis of a series of unsubstituted naphthyl-, pyrenyl- and anthracenyl-fused zinc porphyrin derivatives. To this aim, meso-substitued porphyrins are synthesized and the fusion of the PAHs (Polycyclic Aromatic Hydrocarbon) on the beta-positions are performed through thermally induced dehydro-aromatization. The fused zinc-porphyrin derivatives are fully characterized and their optical absorption and photoluminescence properties are reported. We also demonstrate that zinc can be removed from the porphyrin core, giving rise to pure C, H, N materials. This work constitutes the first step towards the synthesis of the fully-fused tetra-anthracenylporphyrin.

Automated summary

This study reports the synthesis of a series of zinc porphyrin derivatives fused with unsubstituted naphthyl, pyrenyl, and anthracenyl moieties, achieved through thermally induced dehydro-aromatization of meso-substituted porphyrins. The optical properties of the fused zinc porphyrin derivatives were characterized, and the removal of zinc from the porphyrin core to obtain pure C, H, N materials was demonstrated, marking the first step towards the synthesis of fully fused tetra-anthracenylporphyrin.