Rational Synthesis of Benzoheterole-fused Porphyrins and p-System Switching by Central Metal Ion

We developed a rational synthetic approach for benzoheterole-fused porphyrins and demonstrated the synthesis of benzothiophene- and indole-fused porphyrins using the approach. The fused porphyrins exhibited red-shifted absorption and fluorescence due to the effective pi-expansion through heterole-fused structures. In addition, the pi-circuit of indole-fused porphyrin can be switched by a central metal ion.

Automated summary

A rational synthetic approach for benzoheterole-fused porphyrins was developed and applied to the synthesis of benzothiophene- and indole-fused porphyrins. The resulting fused porphyrins exhibited red-shifted absorption and fluorescence, attributed to effective pi-expansion through heterole-fused structures. Furthermore, the pi-circuit of the indole-fused porphyrin could be controlled by a central metal ion.