Progress of antiaromatic ring-contracted porphyrinoids

Abstract

<p indent="0mm">Antiaromatic ring-contracted porphyrinoids have fewer pyrrole units or <italic>meso</italic> carbons than standard 18π-conjugated aromatic porphyrins and exhibit a 4<italic>n</italic> π-conjugation system, with representative molecules including 16π-conjugated norcorrole, corrole, and triphyrin. Antiaromatic ring-contracted porphyrins exhibit great molecular rigidity, excellent stability, and simplicity of functionalization, as well as intense paratropic induced ring current, strong magnetic shielding effect, small highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gap, and high charge transfer capability. This review introduces recent advances in the synthesis and functionalization of antiaromatic ring-contracted porphyrins, and highlights their promising utility in electronic materials based on aromatic-antiaromatic conversion, rechargeable battery electrode materials, and supramolecular conductive materials.