Synthesis and properties of azaphthalocyanines with 1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine moiety

Abstract

New metal-free and zinc azaphthalocyanines (AzaPc) containing peripheral tetrahydropyrazino moiety were prepared from 5,8-disubstituted (ethyl, phenyl, benzyl) 5,6,7,8-tetrahydropyrazino-[2,3-b]

Tetrapyrazinoporphyrazines and their metal derivatives. Part I: Synthesis and basic structural information

“…In particular, this is valid if the dinitriles Pyz89 or Pyz90 with a stable six membered ring (e.g., morpholine or tetrahydropyrazine) are formed (Scheme 19) [148,159,162]. Interestingly, the formation of Pyz90a with a six-membered ring was described also in the reaction of Pyz53 with N 1 ,N 1 ,N 2 -triethylethane-1,2-diamine where the reaction mechanism must necessarily include also a dealkylation step [159].…”

“…Zn II or Mg II complexes of the alkylamino or arylamino TPyzPzs can be also obtained by heating of the corresponding metal free derivatives and metal acetates in pyridine [159,229] or in DMF [49,143,159,163,166,168], although the reaction times need to be extremely prolonged when compared with the times used for the corresponding S or O isosteres, due to the strong electron-donating character of the alkylamino substituents [229].…”

Synthesis of Iron(II) Octachlorotetrapyrazinoporphyrazine, Molecular Structure and Optical Properties of the (X−)2FeTPyzPACl8 Dianions with Two Axial Anionic Ligands (X− = CN−, Cl−)

“…[25,26,34] We use commercially available 1,2-dichloro-4,5-dicyanopyrazine from TCI. Synthetic procedure was modified using 1-chloronaphthalene as solvent and iron(II) acetylacetonate as a source of iron.…”

“…Now various methods for preparing substituted tetrapyrazinoporphyrazines with different donor substituents were developed. [22][23][24][25][26][27] Electron-withdrawing substituents such as cyano-, sulfophenyl-, 2-pyridyl and 2-(N-methyl)-pyridiniumyl are used to increase the acceptor ability of tetrapyrazinoporphyrazines. [21,[28][29][30][31] Molecular structure of pyridine substituted tetrapyrazinoporphyrazine is determined by single-crystal X-ray analysis for cobalt(II) tetrakis[5,6-di(2-pyridyl)-2,3-pyrazino}porphyrazine, Co II TPyzPAPy 8 .…”

New Nitrogen-Containing Five-Membered Heterocyclic ortho-Dicarbonitriles for Preparation of Macroheterocycles

“…These compounds are the most commonly used precursors for the preparation of various macroheterocyclic systems including tetrahetarenoporphyrazines, [1] porphyrinoids, [2] triazaporphyrins, [3] crown phthalocyanines, [4,5] azaphthalocyanines, [6] carborane substituted phthalocyanines, [7] phthalocyanine-fullerene conjugates, [8] binuclear phthalocyanines, [9] and a number of other metalfree phthalocyanines and their metal complexes. [10][11][12][13] Although they have unique chemical and thermal stabilities, phthalocyanines are practically insoluble in water and most organic solvents.…”