Unmetallated and metallated phthalocyanines bearing oxadiazole groups: Synthesis, photophysical and photochemical studies

• Published in: Journal of luminescence Vol. 154; pp. 15 - 21
• Main Authors: Nas, Asiye, Kantekin, Halit, Durmuş, Mahmut, Gümrükçüoğlu, Nurhan
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 01.10.2014; Elsevier
• Subjects: Condensed matter: electronic structure, electrical, magnetic, and optical properties; Diamagnetism, paramagnetism and superparamagnetism; Exact sciences and technology; Magnetic properties and materials; Magnetic resonances and relaxations in condensed matter, mössbauer effect; Metallated phthalocyanine; Nuclear magnetic resonance and relaxation; Optical constants: refractive index, complex dielectric constant, absorption, reflection and transmission coefficients, emissivity; Optical properties and condensed-matter spectroscopy and other interactions of matter with particles and radiation; Optical properties of bulk materials and thin films; Oxadiazole; Photochemical; Photophysical; Physics; Singlet oxygen; Unmetallated phthalocyanine; Oxadiazole; Singlet oxygen; Photophysical; Unmetallated phthalocyanine; Metallated phthalocyanine; Photochemical; Lead oxide; Cobalt Chlorides; Nitrogen heterocycle; Paramagnetism; Singlet state; Infrared spectra; Cobalt; Zinc; Macrocycle; Transition elements; Oxadiazole derivatives; Nuclear magnetic resonance; Absorption spectra; Phthalocyanines; Lead chloride; Organic compounds; Oxygen nitrogen heterocycle
• ISSN: 0022-2313; 1872-7883
• DOI: 10.1016/j.jlumin.2014.03.058

Unmetallated (4) and metallated (zinc(II), cobalt(II), lead(II)) phthalocyanines (5–7) carrying four 4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenoxy) groups on the peripheral positions were synthesized by cyclotetramerization of 4-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenoxy)phthalonitrile (3) in the presence of corresponding metal salts (zinc(II) acetate, cobalt(II) chloride, lead(II) oxide) for metallated and without any metal for unmetallated phthalocyanines. The obtained organo-soluble phthalocyanines were characterized by infrared, electronic absorption, nuclear magnetic resonance and mass spectral techniques and elemental analysis as well. The photophysical and photochemical properties of newly synthesized tetra-substituted unmetallated (4), zinc(II) (5) and lead(II) (7) phthalocyanines were reported in N,N-dimetilformamid (DMF). The synthesized phthalocyanine compound 6 was not evaluated for photophysical and photochemical studies due to open shell and paramagnetic behavior of cobalt(II) metal ions in the phthalocyanine cavity. •Synthesis of unmetallated and metallated phthalocyanines.•Photophysical and photochemical properties of tetra-substituted phthalocyanines.•Characterization of organosoluble phthalocyanines by several spectral techniques.