Novel highly water soluble zinc(II) phthalocyanines: Synthesis, photochemistry and DNA binding behaviours

Novel highly water soluble Zn(II)Pcs containing twelve quaternizable pyridinium groups were designed by taking advantage of the existence of the pentaerythritol hub in each substituted group. In the synthetic pathway, first the peripheral and non-peripheral tetra-2,2,2-tris[(pyridin-2-ylthio)methyl]ethoxy-substituted neutral Zn(II)Pcs (4 and 5) were synthesized and then quaternizations of twelve pyridine groups gave rise to reach highly water soluble novel Zn(II)Pcs (6 and 7). The three-branched bulky nature of substituted groups was effective in pre-venting aggregation and increasing dissolution. The photophysical, photochemical and singlet oxygen-producing properties of all studied compounds and also the DNA binding behaviours of quaternized Zn(II)Pcs were pre-sented here.

Automated summary

Highly water soluble Zn(II)Pcs with twelve quaternizable pyridinium groups were designed using pentaerythritol hub. Peripheral and non-peripheral tetra-2,2,2-tris[(pyridin-2-ylthio)methyl]ethoxy-substituted neutral Zn(II)Pcs (4 and 5) were synthesized first, followed by quaternizations of twelve pyridine groups to obtain highly water soluble Zn(II)Pcs (6 and 7). The branched nature of substituted groups prevented aggregation and increased dissolution. The photophysical, photochemical, singlet oxygen-producing properties, and DNA binding behaviors of quaternized Zn(II)Pcs were studied.