Porphyrins and their analogous are excellent scaffolds for advanced investigation of the macrocyclic π aromaticity. The aromaticity of various porphyrinoid systems has been extensively investigated. Several factors, such as the molecular framework's topology, the molecule's conformation, metal coordination in the inner core, and tautomerism, can determine their π-electron conjugation. The macrocycles combining the structural features of ansametallocenes and heteroporphyrin were obtained. The reported ferroceno-and ruthenocenoporphyrinoids provide evidence for direct transmission of π-electron conjugation across a d-electron ferrocene and ruthenocene, respectively (1, 2; Figure ). In the case of ruthenocenothiaporphyrin and ruthenocenoporphyrin, the corresponding macrocyclic antiaromaticity and aromaticity observed for the same number of π electrons were controlled by the mutual orientation of the cyclopentadienyl (Cp) rings. Recently, the effective π-conjugation through d-orbitals of the metal center, resulting in the antiaromatic character of the platinacorrole complex, has also been documented (3, Figure ). The metallocene unit can be incorporated into the macrocyclic platform in three different modes: 1,1'; 1,2 and 1,3, as shown in Figure . To date, several bridged 1,1'-metallocene macrocycles have been reported. Except for a few examples involving the porphyrinoids 1 and 2, macrocyclic πconjugation is impossible due to structural and/or conformational features. On the other hand, metallocenes that are 1,2-and 1,3disubstituted and incorporated into a cyclic framework (Figure ) are exceedingly uncommon. The incorporation of metallocene subunits at the 1,2 or 1,3 positions into fully π-conjugated macrocycles is of fundamental importance in determining the overall electronic properties of the created hybrid molecules. The recent approach of direct metal π complexation to various oligopyrrolic ligands has been shown to modulate their spectroscopic, redox, optical, and electronic properties. In this approach, a direct coordination of [RuCp] + , [RuCp*] + (Cp*, pentamethylcyclopentadienyl), or [Ru(p-cymene)] + fragment to pyrrole π-surface of π-conjugated porphyrins (4), porphycenes (5) and hexaphyrins has been investigated (Figure ). In these complexes with a "fused" 1,3-azaruthenocene moiety (4, 5; Figure ), strong electronic azaruthenocenemacrocycle communication was observed. The synthesis of β,β'-fused cyclopentenylporphyrins allowed the introduction of a metallocene at the macrocyclic periphery (6, Figure ). A different coordination motif of pentamethylcyclopentadienyl ruthenium cation is represented by "sitting-atop" semisandwich complexes of porphycene 7, Nfused porphyrin, and N-confused porphyrin 8, in which a [RuCp*] + fragment is accommodated in the central N3/N4 core of the macrocycle.