Microwave-assisted synthesis and characterization of phthalocyanines substituted with azo compound containing eugenol moiety

KANTAR C., MERT F., ŞAŞMAZ S.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, cilt.696, sa.18, ss.3006-3010, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 696 Sayı: 18
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1016/j.jorganchem.2011.05.014
  • Dergi Adı: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3006-3010
  • Anahtar Kelimeler: Phthalocyanine, Microwave, Synthesis, Phthalonitrile, Eugenol, Azo dyes, DERIVATIVES
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

The new metallophthalocyanines (Co, Ni, Cu, and Zn) substituted with azo compound containing eugenol moiety are described. Firstly, azo compound (I) containing eugenol moiety was synthesized by treating eugenol with p-hydroxyaniline. Then phthalonitrile compound (1) was synthesized by microwave-assisted synthesis method. The purification of phthalonitrile compound (1) was carried out by column chromatographic separation. Intramolecular hydrogen bonding in the azo compound (I) prevent base-catalyzed nucleophilic aromatic substitution of OH group belongs eugenol. At the last step, metallophthalocyanines (1a, 1b, 1c, and 1d) were synthesized by the microwave irradiation. The microwave-assisted synthesis method reduces reaction times and enhances the yield of the reactions. All phthalocyanine compounds are soluble in DMF and DMSO. The structures were confirmed by elemental analysis, H-1 NMR, C-13 NMR, UV/Vis, IR and Mass spectra. (C) 2011 Elsevier B. V. All rights reserved.