A panchromatic pyrazine-fused porphyrin dimer

Functionalized heterocycle-appended porphyrins: catalysis matters

“…Notably, the mechanism of dimer formation, method for its targeted preparation, and complete investigation of its spectral features were reported by us previously. 28 The results of the performed series of condensation reactions are summarized in Table 1. 4-Bromobenzaldehyde (3a) was used as a reference aldehyde for comparison of the obtained results with the previously reported data. 35 Thus, the interaction of 2 with 3a in a 1 : 1 molar ratio provided a mixture of 4a and 5a with 73% and 12% yield, respectively ( Table 1, entry 1), that is consistent with the result found for the related tetramesitylporphyrin (Scheme 1).…”

“…The solvents were puried according to conventional methods. 45 The starting 2-amino-3-nitro-tetrakis(4-butoxyphenyl)porphyrinato nickel(II) 1, 28,36,46 2-amino-3-nitro-tetramesitylporphyrinato nickel(II), 35 and 4-diethoxyphosphorylbenzaldehyde 3g 44,47 were prepared following the conventional procedures. 2,3-Diaminotetramesitylporphyrinato nickel(II) 7 was generated following the published procedure.…”

“…17,[23][24][25][26][27][28][29][30][31][32][33] Recently, we developed synthetic strategies towards imidazole-and pyrazine-annulated porphyrins starting from tetrapyrrole dioxo-or diamino-derivatives and aromatic aldehydes. 28,[34][35][36][37][38] The sterically hindered tetrapyrrole was used as a synthetic platform for the development of bifunctionalized linear and angular annulated polyaromatic compounds, water soluble derivatives for biomimetic applications and macrocycles with terminal anchoring groups. 34,38 Furthermore, the latter methodology was implemented for the elaboration of a novel class of heteroleptic sandwich-type lanthanide (porphyrinato)(phthalocyaninates) 39,40 based on heterocycle-appended porphyrin ligands.…”