New water soluble phenoxy phenyl diazenyl benzoic acid substituted phthalocyanine derivatives: Synthesis, antioxidant activities, atypical aggregation behavior and electronic properties

Ağırtaş, Mehmet; Çelebi, Metin; Gümüş, Selçuk; Ozdemir, Sadin; Okumus, Veysi

doi:10.1016/j.dyepig.2013.05.019

New water soluble phenoxy phenyl diazenyl benzoic acid substituted phthalocyanine derivatives: Synthesis, antioxidant activities, atypical aggregation behavior and electronic properties

Atıf İçin Kopyala

Ağırtaş M. S., Çelebi M., Gümüş S., Ozdemir S., Okumus V.

DYES AND PIGMENTS, cilt.99, sa.2, ss.423-431, 2013 (SCI-Expanded)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 99 Sayı: 2
Basım Tarihi: 2013
Doi Numarası: 10.1016/j.dyepig.2013.05.019
Dergi Adı: DYES AND PIGMENTS
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED)
Sayfa Sayıları: ss.423-431
Anahtar Kelimeler: Phthalocyanines, Phthalonitrile derivatives, Antioxidant activities, Aggregation, Solubility, DFT, AZO-CHROMOPHORE, ZINC, PHTHALONITRILES, INHIBITORS
Van Yüzüncü Yıl Üniversitesi Adresli: Evet

Özet

Novel substituted phthalonitrile derivatives were obtained by the reaction of 2-(4-hydroxyphenylazo) benzoic acid and 4,5-dichloro-1,2-dicyanobenzene, or 4-nitrophthalonitrile. Peripherally phenoxy phenyl diazenyl benzoic acid substituted zinc (II) phthalocyanine complexes, and their sodium salts were synthesized and characterized for the first time. The newly synthesized phthalocyanine complexes show excellent solubility in water. The aggregation investigations carried out in different concentrations indicate that phenoxy phenyl diazenyl benzoic acid-substituted phthalocyanine compounds do not have any aggregation behavior for the concentration range of 7.00 x 10(-5)-4.38 x 10(-6) M in DMF. The antioxidant activities of DMF solution of compounds were analyzed through radical scavenging, and chelating ability to Fe2+ cation. Additionally, new compounds did not show any antibacterial activity against some selected bacteria cultures. Moreover, the ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G(d,p) level in order to obtain information about the 3D geometries and electronic structure. (C) 2013 Elsevier Ltd. All rights reserved.