3 Porphyrins: Syntheses and Properties
75
Fig. 3.29 Oxidative dimerization of aminoporphyrins
bisZn complex 109 is interchanging rapidly between a (M, M)-form and a (P, P)-form
and binding (R)-1-phenylethylamine induced helical sense bias in favor of the (M,
M)-form with 65:35 diastereoselectivity (Ito et al. 2016).
Fujimoto and Osuka demonstrated that π-conjugation between two porphyrin
cores is much more enhanced by 1,5-naphthyridine-fusion in comparison with the
pyrazine-fusion seen in 106 (Fujimoto and Osuka 2018). The 1,5-naphthyridinefused diporphyrin 112 was obtained in 84% yield by Pt(II)-catalyzed cyclization
of bisNi(II) complex of β-to-β ethynylene-bridged meso-aminoporphyrin dimer 111
followed by oxidation with PbO 2 (Fig. 3.30). Ni(II) complex 111 was prepared
starting from β-borylporphyrin 83 by NIS-CuI iodination, (Fujimoto et al. 2014)
Fig. 3.30 1,5-Naphthyridine-fused diporphyrin
75
Fig. 3.29 Oxidative dimerization of aminoporphyrins
bisZn complex 109 is interchanging rapidly between a (M, M)-form and a (P, P)-form
and binding (R)-1-phenylethylamine induced helical sense bias in favor of the (M,
M)-form with 65:35 diastereoselectivity (Ito et al. 2016).
Fujimoto and Osuka demonstrated that π-conjugation between two porphyrin
cores is much more enhanced by 1,5-naphthyridine-fusion in comparison with the
pyrazine-fusion seen in 106 (Fujimoto and Osuka 2018). The 1,5-naphthyridinefused diporphyrin 112 was obtained in 84% yield by Pt(II)-catalyzed cyclization
of bisNi(II) complex of β-to-β ethynylene-bridged meso-aminoporphyrin dimer 111
followed by oxidation with PbO 2 (Fig. 3.30). Ni(II) complex 111 was prepared
starting from β-borylporphyrin 83 by NIS-CuI iodination, (Fujimoto et al. 2014)
Fig. 3.30 1,5-Naphthyridine-fused diporphyrin