Syntheses of Trisulfonated Phthalocyanines and Their Derivatives Using Boron(III) Subphthalocyanines as Intermediates

Phthalocyanines: The Need for Selective Synthetic Approaches

“…This reaction has proved to be very selective and efficient in some cases, and it has also allowed the synthesis of previously unattainable phthalocyanines. [28,29] From the results obtained by us and others, [30Ϫ34] it is now clear that the outcome of this synthetic method depends very much on the reaction conditions and on the characteristics of the starting materials. A typical ring expansion is accomplished by the addition of a 6Ϫ9 molar excess of the diiminoisoindoline derivative to a solution of the subphthalocyanine in DMSO/1-chloronaphthalene or dichlorobenzene (1:4 to 4:1) or (dimethylamino)ethanol, and leaving the reaction mixture at 80Ϫ100°C for 5Ϫ12 h. The desired unsymmetrically substituted Pcs are obtained in yields ranging from 3Ϫ90%.…”

Synthese und strukturelle Charakterisierung von Borsubphthalocyaninaten

“…[9]. Letzterer Komplex, der in Aceton gut, in Dichlormethan dagegen wenig lo È slich ist, la È sst sich auch in Anlehnung an [8] Fu È r die Subphthalocyaninate beobachtet man unu È bersichtliche, jedoch charakteristische Schwingungsspektren [22], wie dieses in Abb. 6 [25].…”

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

“…Another selective approach, which was applied for the synthesis of porphyrazines bearing one pyrazine ring, is based on the expansion of a subphthalocyanine (SubPc) ring in the presence of the pyrazine containing precursor (diiminoimide [293][294][295] or dinitrile [296], Scheme 46). In such a way water soluble anionic monopyrazinotribenzoporphyrazine [TriBzPyz24PzH 2 ] (R = SO 3 Na, R'= Ph) has been prepared from boron trisulfosubphthalocyanine and diiminoimide obtained from 5,6-diphenyl substituted dinitrile Pyz24 in DMSO.…”