A new hexadeca substituted non-aggregating zinc phthalocyanine

• An amphiphilic ZnPc with hexyloxy and diethylaminophenoxy groups was synthesized.
• Hexadeca substitution lowers the tendency of ZnPc for aggregation in water.
• Singlet oxygen generation capability of the ZnPc was shown by photooxidation of DPBF.
• High sensitivity of ZnPc for trace amount of acid was shown by UV–Vis spectra.

In this work, a new hexadeca substituted zinc phthalocyanine 4 bearing hexyloxy groups in nonperipheral positions and 3-(diethylamino)phenoxy groups in peripheral positions and its corresponding water-soluble octacationic derivative 5 have been reported. The new compounds have been characterized by elemental analysis, IR, UV, NMR and mass spectra. Zinc phthalocyanine showed excellent solubility in organic solvents of wide polarity range due to its amphiphilic nature and it enabled us to carry out detailed UV–Vis studies in different solvents. Octacationic zinc phthalocyanine 5 was soluble in DMF, DMSO and water. UV–Vis spectra of 5 in DMSO, DMF and water showed sharp Q band absorption as an indication of monomeric form even in aqueous media. This property of water-soluble non-aggregating zinc phthalocyanine is promising as a photosensitizer in Photodynamic Therapy of Cancer.

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