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The macrocyclic structures with local conjugation readily undergo a redox-triggered change in the diatropic character, leading to a global current–density pathway of the doubly charged systems. The figure-eight geometry of the neutral dimer does not significantly change upon oxidation according to the spectroscopic and computational data. The oxidation leads to 3D cross-conjugation at the intersection of the two ethylene bridges resulting in a global ring current.

The 14π-electron system of anthracene has been merged with the unsaturated Z-1,2-difurylethene to form a macrocycle(s) with the retained local conjugation of all incorporated subunits that were substantially modulated with a redox activation, opening a global delocalization involving all integrated aromatics. In addition, the edge modulation of acene via the attachment of a specific isomer of the conjugated system gives steric confinements that are characteristic of small macrocycles, forcing substantially short C(H)···O electrostatic interactions that are documented spectroscopically with the support of X-ray analysis.

A macrocyclic motif composed of carbazole and pyridine subunits linked by a carbonyl bridge (C═O) forms a skeleton with a peripheral reactivity that leads to a pinacol-like coupling activated by BBr3, eventually entrapping a substantially elongated C–C bond. Slightly modified conditions lead to the efficient transformation of the C═O unit to a CH2linker that, after exposure to air, gives a dimeric molecule with multiple bonds between two macrocyclic units, as documented in spectroscopy and X-ray analysis.

A three-component reaction of antiaromatic meso-mesityl-3-nitronorcorrolatonickel(II) 1-NO2with dialkyl acetylenedicarboxylate and PBu3yields aromatic zwitterionic corrole nickel(II) complexes 3-R with one of the meso-substituents comprising a positively charged tributyl phosphonium group and negatively charged coordination core. Reaction of 1-NO2with PBu3alone resulted in a nonaromatic chiral adduct 5of a zwitterionic phlorine character with a −PBu3+group at a pyrrole β-position.