Novel, Highly Soluble Non-Peripherally Phthalocyanines Bearing Bulky Groups Containing Fluorine Atoms: Synthesis, Characterization, Spectral and Improved Photophysicochemical Properties

Yaşa Atmaca G., Erdoğmuş A.

Hacettepe Journal of Biology and Chemistry, vol.45, no.1, pp.11-20, 2017 (Peer-Reviewed Journal)


The synthesis of a new phthalonitrile (1) was described by treating 3-nitrophthalonitrile with 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio)phenol. After that, its soluble zinc(II) (2), magnesium(II) (3), cobalt(II) (4) and indium chloride(III) (5) non-peripheral phthalocyanine derivatives were reported for the first time. The newly synthesized metallo phthalocyanine derivatives were characterized by mass spectrometry, UV-Vis, FT-IR, and 1H-NMR spectroscopy. Photochemical and photophysical (photodegradation, singlet oxygen and fluorescence quantum yields) properties of the phthalocyanines were carried out in tetrahydrofuran (THF). Metallo-phthalocyanines, which containing a bulky long alkyl chain bearing fluorine atoms, have high solubility in known organic solvents such as THF, dichloromethane (DCM), chloroform (CHCl3) and toluene and do not show aggregation. Besides, the effect of metal ion types in phthalocyanines core (2, 3, 4 and 5) were also investigated. The effects of the substitution with fluoroalkynyl-functionalized groups on these parameters mentioned were also compared along with the previously synthesized peripherally tetra and octa substituted phthalocyanines. Non peripherally position of the substituents on Pc improved photophysical and photochemical properties.