ChemInform Abstract: Symmetric Sterically Hindered Phthalocyanines.

Abstract

ChemInform Abstract The tetralindicarbonitrile (I), prepared from 1,1,4,4,6,7-hexamethyltetralin by common methods, is treated with sodium isoamylate to give the phthalocyanine (II). Cyclization in the presence of vanadyl, cobalt, copper, or zinc salts results in the formation of the corresponding metal phthalocyanines.

Phthalocyanines and Related Compounds: XL. Synthesis of β-Diethylaminoethyl-substituted Octa-4,5-carboxyphthalocyanine Tetraimides and Their Quaternary Salts

“…The resulting quaternary salts were extremely hygroscopic, very readily soluble in water and dilute hydrochloric acid, and soluble in alcohols and aprotic polar solvents like DMSO or DMF. Unlike DMSO, the electronic absorption spectra of these salts in aqueous solution revealed a considerable aggregation [5].In the present work we synthesized previously unknown N,N`,N``,N```-tetrakis(b-diethylaminoethyl)-phthalocyanine-2,3 : 9,10 : 16,17 : 23,24-tetrakis(dicarboxamide) complexes with cobalt(II) (Ia), hydroxoalyuminum (Ib), zinc(II) (Ic), and iron(II) (Id) and the corresponding water-soluble quaternary salts (II3VI) by the action of methyl iodide, methyl p-toluenesulfonate, diethyl and dimethyl sulfates, and trimethyl phosphate. Compounds Ia3Id were prepared by reaction of phthalocyanine-2,3 : 9,10 : 16,17 : 23,24-tetrakis(dicarboxanhydride) complexes with N,N-diethylethylenediamine, and the resulting N-substituted imides were treated with the above listed alkylating agents.…”

“…The resulting quaternary salts were extremely hygroscopic, very readily soluble in water and dilute hydrochloric acid, and soluble in alcohols and aprotic polar solvents like DMSO or DMF. Unlike DMSO, the electronic absorption spectra of these salts in aqueous solution revealed a considerable aggregation [5].…”

“…The products were soluble in organic solvents and water, and their molecules retained the D 4h symmetry typical of unsubstituted phthalocyanine. However, we found that these compounds strongly tend to aggregate in aqueous media [2,3]. With a view to eliminate aggregation, we synthesized a new series of water-soluble conjugates from anionic carboxyphthalocyanine complexes and sulfo analogs of a-amino acids, namely taurine-substituted octa-4,5-carboxyphthalocyanine complexes [4,5].…”

“…However, we found that these compounds strongly tend to aggregate in aqueous media [2,3]. With a view to eliminate aggregation, we synthesized a new series of water-soluble conjugates from anionic carboxyphthalocyanine complexes and sulfo analogs of a-amino acids, namely taurine-substituted octa-4,5-carboxyphthalocyanine complexes [4,5]. The resulting tetra-N-(2-sulfoethyl)imides (as free acids or sodium salts) were fairly readily soluble in water, ethanol, and dilute hydrochloric acid.…”

“…We previously [2,3] synthesized a series of covalent conjugates from anionic octa-4,5-carboxyphthalocyanine metal complexes and a-amino acids, namely the corresponding tetra-N-carboxymethylimides and octa-4,5-N-methyl-N-carboxymethylcarboxamides. The products were soluble in organic solvents and water, and their molecules retained the D 4h symmetry typical of unsubstituted phthalocyanine.…”