Isomeric separation and identification of tetra-, tri-, and di-β-sulphonic phthalocyanine zinc complexes

Abstract

The synthesis, isomeric separation, and identification of β-sulphonic phthalocyanine zinc complexes were reported. While the sulphonic phthalocyanines have been studied extensively, the development of separation technology may enable deeper insights into their isomeric constitution. An ion-pair reversed-phase high performance liquid chromatography (IP-RP-HPLC) method was developed to separate the sulphonic phthalocyanine isomers. The results showed that the product of the condensation reaction is a mixture of all possible isomers with statistical distribution. Several isomers were obtained and structural determination was undertaken by NMR. Based on the IP-RP-HPLC elution sequence of these well-identified isomers, a relationship between the structure and efficiency was deduced: closely spaced intervals of sulphonic groups lead to higher hydrophobicity and shorter retention times on HPLC. Based on this relationship, each HPLC peak was assigned to the corresponding isomeric structure.

Enhanced fluorescence of tetrasulfonated zinc phthalocyanine by graphene quantum dots and its application in molecular sensing/imaging

“…4‐(Potassium sulfonate) phthalonitrile and ZnPcS 4 were synthesized in our laboratory as previously reported . In brief, ZnPcS 4 was obtained by condensing 4‐(potassium sulfonate) phthalonitrile and anhydrous zinc acetate in 2‐ethoxyethanol with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene as the catalyst.…”

Investigation on 1O2 generation ability of di‐sulfonic phthalocyanine zinc isomers using an HPLC–CL system

“…This sample contains five isomers (chemical structures in Fig. 1) (11,17). 1) and three of which are cis-isomers (ZnPcS 2 -3 to ZnPcS 2 -5 in Fig.…”

“…Previously (11,17), we have studied the HPLC separation of ZnPcS 2 , and all the five HPLC peaks had been assigned to corresponding isomers. Our results verified that the substitution pattern of sulfonic groups on phthalocyanine macrocycle notably affected the hydrophilicity of molecules.…”

“…cis-isomers have normal Q-band absorptions, whereas trans-isomers have splitting Q-band absorptions (10)(11)(12)(13). Here, we report a simple method to compare the 1 O 2 production ability of di-sulfonic phthalocyanine zinc (II) (ZnPcS 2 ) isomers.…”

Biomimetic self-assembling acylphthalocyanines

“…16 An elegant study of water soluble Pc's, with a view on photodynamic therapy applications, stands out by the very careful experimentations and the efficient HPLC separations. 17 Even more complex mixtures resulted in our hands when the protected phthalodinitriles 4a-d (A) were submitted to a mixed condensation with the unsubstituted phthalodinitrile (B in Scheme 2). In these cases, beside the four regioisomers A 4 of type ZnPc-5, highly colored Pc's having one, two, or three dioxolane (D) protected acyl residues were formed, beside some unsubstituted ZnPc (B 4 in Scheme 2) which could be easily separated due to its limited solubility.…”