Octakis(alkylthio)-substituted phthalocyanines and their interactions with silver(I) and palladium(II) ions

Abstract

Metal-free phthalocyanines and metal phthalocyaninates ( M = Ni, Cu, Co or Zn) carrying eight alkylthiogroups on peripheral positions have been synthesised from 4.5-bis(alkylthio)phthalonitrile and 1,8diazabicyclo[5.4.0]undec-7-ene (dbu) or the corresponding anhydrous metal salt [NiCI,, CuCI, CoCI, or Zn (O,CMe),]. The resulting compounds reacted with silver(1) or palladium(ll) salts to form complexes with a phthalocyanine: metal ratio of 1 : 4. Spectrophotochemical investigation of these reactions revealed that complexation with Ag' results in aggregation, while the addition of Pd" destroys the aggregation and yields a new Q band at 720 nm.

Dioxa-dithia Macrocycle-bridged Dimeric with Hexakis(alkylthio) Substituents and Network Polymer Phthalocyanines

“…Here excess iminoisoindoline derivative 5 resulted in the formation of a corresponding polymeric metal-free derivative of the iminoisoindoline 5 reactant together with the desired dimeric phthalocyanine 11, but they were easily separated by column chromatography. The dodekis(hexylthio)-substituted dimeric phthalocyanine 11 is extremely soluble in apolar solvents like the subPc 10 or the symmetrically octakis(alkylthio)-substituted phthalocyanines [22,42]. Anhydrous zinc(II) acetate has been used in a high boiling solvent (e.g.…”

Synthesis and electrochemical properties of benzyl-mercapto and dodecyl-mercapto tetrasubstituted manganese phthalocyanine complexes

“…4-Nitrophthalonitrile, 4-(benzyl-mercapto) phthalonitrile and 4-dodecylmercaptophthalonitrile were synthesized according to procedure in literature [16] and [17]. Potassium carbonate and manganese(II)acetate salts were obtained from SigmaAldrich and were used as received.…”

Synthesis and characterization of new metal-free and metal phthalocyanines with peripheral N'-2-(cyanoethyl)-aminoethylsulfanyl substituents

“…Starting from simple mono-functional substituents such as halides and alkyl, alkoxy and sulfo groups which cause only small changes in the physical properties of the parent molecules, more complex structures have been introduced on the periphery of the phthalocyanine nucleus [5]. Among the many we may cite are crown ether [6][7][8][9][10], tetraaza [11][12][13], or diazatrioxa [14,15] macrocycles, tetraaza-crown ether double layers [16] and alkyl sulfides [17][18][19].…”