Two new expanded porphyrins, naphthorubyrin and naphthosapphyrin, were synthesized. The π-extended rubyrin was isolated and structurally characterized in its monoprotonated form. The sapphyrin congener undergoes pyrrole inversion as a function of the protonation state. These conformational effects are reflected in the spectroscopic features, including the excited singlet state lifetimes.

Oxasmaragdyrin boron complexes were prepared and applied in DSSCs. The HOMO-LUMO energy gap analyses and theoretical calculations revealed that these expanded porphyrins are ideal sensitizers for DSSCs. A device containing oxasmaragdyrin-BF2 as the sensitizer achieves an energy conversion efficiency of 5.7%.

Upon treatment with tetrabutylammonium fluoride (TBAF), [32]heptaphyrins 1 and 2 underwent conformational changes to form Möbius aromatic species, as indicated by the appearance of sharp and intense B-like bands and distinct Q-like bands, long-lived S1-states, and relatively large TPA cross-section values. Hence, deprotonation has been shown to be an additional effective means to induce the for...

This review summarizes recent developments in the area of porphyrin chemistry in the direction of biological applications. Novel synthetic methodologies are reviewed for porphyrin synthesis, porphyrin analog synthesis, stable porphyrinogens -- calixpyrroles, expanded porphyrins. Unique biological properties of those compounds are desribed with focus on photodynamic therapy (PDT) and molecular r...