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C. Le-gac, S. Boitrel, B. J. New, H. Mori, Y. M. Sung et al., Nitrogen containing ligands such as pyridyl, 5- formyl-2-pyrryl and imidazolyl have been introduced at meso positions of hexaphyrins and octaphyrins In some metal complexes, these groups participate to the coordination sphere of the metals 20 Hexaphyrins bearing electron withdrawing or sterically hindered substituents at meso positions turn to be more stable, see ref 19 22 Distance of Me-tren (13 atom mean plane) to hexaphyrin (36 atom centroid) = 3.536 Å. 23 UV-vis absorption spectra were recorded at all steps of the NMR complexation study (Figure 6b-d), and this study was also performed at UV-vis concentration. In both cases, addition of Zn(OTf)2 to 8 did not afford clear optical signatures, Zn(II) complexation being always incomplete. These NMR and spectroscopic data suggest the formation of labile Zn(II) complex(es) of 8, not yet determined. 24 Protons in ? and ? positions relative to the nitrogen atom are indeed shielded by 1.12 and 0.44 ppm (SI) Although the exo-coordination of BuNH2 orients the alkyl chain outwards, a shielding environment may arise from the two surrounding aromatic moieties Ar3 and Ar5 (Scheme 3) 25 In these conditions, 1 equiv. of TBAOTf and 1 equiv. of TfOH are formed upon Zn(II) metallation. 26 The protonated and neutral complexes are in a fast exchange regime on the NMR time scale at 298 K, Ge(IV) Möbius hexaphyrin complexes with a single exogeneous phenoxide ligand have been described recently, pp.517-520, 2003.

T. Kim, S. Ishida, T. Tanaka, T. Mori, D. Kim et al., 30 ? = ? cos? i, ?i being the torsional angles along the SMC. The resonance integral between two adjoining carbon sp 2 centers is assumed to scale with cos?i, see ref 1j. 31 Other popular geometric criteria of aromaticity such as HOMA are not reliable in complex polycyclic conjugated compounds and were not included in this study, See: (a) Wannere, pp.3982-3986, 2017.

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. Chem, . E. Int, T. Mori, T. Tanaka, T. Higashino et al., 39 The protonation state of the tren cap of 8 has minor influence on the d.e. (Table 2, entries 6 and 7, pathways A vs. B). 40 The ?? of the acetato are similar to the case of AcO, BuNH2, indicating similar endo/exo selectivity for the coordination to zinc, pp.6619-6621, 2010.