Synthesis, characterization and structural computational investigation of novel Zn(II) phthalocyanines containing peripheral anthracene moieties

Kabay N., Bozer B. D., Kiraz A. O., Baygu Y., Kara A., GÖK Y.

Journal of Porphyrins and Phthalocyanines, vol.23, no.7-8, pp.943-959, 2019 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 23 Issue: 7-8
  • Publication Date: 2019
  • Doi Number: 10.1142/s1088424619500913
  • Journal Name: Journal of Porphyrins and Phthalocyanines
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.943-959
  • Keywords: anthracene, computational chemistry, cyclotetramerization, reduction, zinc phthalocyanine
  • Uşak University Affiliated: Yes

Abstract

New zinc(II) phthalocyanines (ZnPc-I and ZnPc-II) containing four peripheral anthracene pendant groups were synthesized by cyclotetramerization of (E)-4-(3-(4-((anthracen-9-yl-methylene)amino)phenoxy)propoxy)phthalonitrile and 4-(3-(4-((anthracen-9-ylmethyl)amino)phenoxy)propoxy)phthalonitrile. All compounds were characterized using a combination of analytical and spectroscopic techniques such 1H, 13C NMR, FT-IR, UV-vis and MS spectral data. The molecular geometry and gauge including atomic orbital (GIAO) 1H and 13C chemical shift values of the compounds in the ground state have also been calculated using B3LYP with the 6-31G(d) basis set. The chemical shift of the optimized molecular structure is compared with the experimental chemical shift values.