Highly soluble tetra lauryl alcohol substituted phthalocyanines; synthesis, electrochemistry, spectroelectrochemistry

Abstract

The tetra peripherally β-substituted 2(3),9(10),16(17),23(24)-tetrakis undecyloxy phthalocyanine derivatives, M{Pc[O-(CH₂)₁₁CH₃)]₄} Pc: Phthalocyanine, [M: Zn(II)(2), Ga(III)(3), and Ti(IV)(4)], have been synthesized and characterized using FT-IR, ¹H, and ¹³CNMR, MS (MALDI-TOF), UV–vis, atomic force microscopy, electro and spectroelectro chemical and elemental analysis. The new synthesized complexes are soluble in both polar solvents and nonpolar solvents, such as THF, DMF, CHCl₃, CH₂Cl_2, benzene, and even hexane. Electrochemical and spectroelectrochemical measurements give common metal-based and/or Pc ring-based redox processes which support the proposed structures of the complexes. While titanium phthalocyanine exhibits metal- and Pc ring-based reduction and/or oxidation couples, gallium and zinc phthalocyanines give only Pc ring-based electron transfer processes.

Keywords:

• Phthalocyanine
• Zinc
• Gallium and Titanium
• Synthesis
• Spectroelectrochemistry
• Electrocolorimetry

Acknowledgements

We thank the research fund of Sakarya University and TUBİTAK (Project No: BAP-2013-02-04-049, Project No: TBAG-108T094).