Synthesis, Characterization and Electrochemical Investigation of Phthalocyanine Compounds Bearing Fluorine Functionality

Peripherally substituted symmetrical phthalocyanine derivatives have the potential to use in a wide range of high technology applications, such as in catalysis, in photodynamic therapy, in electrochromic display devices, and as a molecular electronics, or magnetic devices. Phthalocyanines possess an extended π-conjugated electron system which permits π stacking between planar macrocycles. Adding substituents to the periphery of the macrocycles increases their solubility since these substituents increase the distance between the stacked phthalocyanines and enable their solvation. The phthalocyanine complexes are also electrochemically precious complexes due to their excellent electrochemical behaviors.  It is well known that the different functionalities changes the features of the MPc complexes, thus electrochemical properties of these complexes should be investigated for possible applications. [1-3]

We present here the syntheses of tetra-substituted fluorine containing biphenyl-malonic ester groups bearing phthalocyanine derivatives with different central metal atoms and investigation of their electrochemical behaviors. All synthesized novel phthalocyanine compounds have been characterized by using their elemental analyses, FT-IR, UV-Vis, ¹H NMR, ¹³C NMR and mass spectroscopic methods. The electrochemical activity of phthalocyanine derivatives were also evaluated from the current–voltage curves obtained by cyclic and differential pulse voltammetric methods.

 

REFERENCES

1-  A. Koca, Y. Arslanoğlu, E. J Electroanal Chem, 616 (2008), pp. 107–116

2- N.B. Mckeown, B. Dunn, J.W. Goodby, A.R. West (Eds.), Phthalocyanine materials: synthesis, structure and function, Cambridge University Press, Cambridge (1998)

3- H.S. Nalwa, J.S. Shirk, C.C. Leznoff, A.B.P. Lever (Eds.), Phthalocyanines: properties and applications, VCH Publishers Inc, New York (1996), pp. 79–181.