New Type of Tetrazine-Substituted Metallophthalocyanines by Microwave Irradiation: Synthesis and Characterization

SAKA E. T., YILDIRIM N., KANTEKİN H.

HETEROATOM CHEMISTRY, vol.21, no.7, pp.456-461, 2010 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 21 Issue: 7
  • Publication Date: 2010
  • Doi Number: 10.1002/hc.20623
  • Journal Name: HETEROATOM CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.456-461
  • Karadeniz Technical University Affiliated: Yes

Abstract

5,6-bis(4-methylphenyl)-2,3-dihydro-1,2,3,4-tetrazine 2 was synthesized by the dimerization of ethyl p-methylbenzoateformylhydrazone 1 in hydrazinehydrate solution. 2,3-bis(4-methylphenyl)-6,7,14,15 - tetrahydro[1,2,3,4] tetrazino [2,3d][1,8, 4,5] benzodithia-diazecine-10,11-dicarbonitrile 4 was sythesized by cyclization reaction of tetrazine monomer 2 onto 1,2-bis-(2-iodoethylmercapto)-4,5-dicyanobenzene 3. Co(II) and Cu(II) phthalocyanine complexes were prepared by reaction of the dinitrile compound (4) with the chlorides of Co(II), Cu(II), and DMAE at 175 degrees C, 350 W in a microwave oven for 10 min. Zn(II)-phthalocyanine complex was prepared by reaction of the dinitrile compound 4 with the acetate of Zn(II) and DMAE at 175 degrees C, 350 W in a microwave oven for 10 min. The new compounds were characterized by a combination of IR, H-1-NMR, C-13 NMR, UV-vis, elemental analysis, and MS spectral data. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:456-461, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20623