Aldehyde Substituted Phthalocyanines: Synthesis, Characterization and Investigation of Photophysical and Photochemical Properties

Sen P., Yildiz S. Z., ERDOĞMUŞ A., Dege N., Atalay Y.

JOURNAL OF FLUORESCENCE, vol.26, no.4, pp.1521-1534, 2016 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 26 Issue: 4
  • Publication Date: 2016
  • Doi Number: 10.1007/s10895-016-1852-x
  • Journal Name: JOURNAL OF FLUORESCENCE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1521-1534
  • Keywords: Synthesis, Single crystal, X-ray structure, Theoretical calculation, Phthalocyanine, Fluorescence property, Singlet oxygen, Photodegradation, ZINC PHTHALOCYANINES, MOLECULAR-STRUCTURE, AGGREGATION, METALLOPHTHALOCYANINES
  • Yıldız Technical University Affiliated: Yes

Abstract

The new free and nickel phthalocyanine derivatives, tetrakis [(2-formylphenoxy)-phthalocyanine (4), tetrakis [(2-formylphenoxy)-phthalocyaninato]nickel(II) (5) have been synthesized via de-protection of tetra acetal-substituted phthalocyanines in acetic acid/FeCl3 system. The starting phthalocyanines, tetrakis [(2-(1,3-dioxolan-2-yl)phenoxy)-phthalocyanine (2) and tetrakis [(2-(1,3-dioxolan-2-yl)phenoxy)-phthalocyaninato]nickel (3), were prepared by the tetramerization of 4-(2-(1,3-dioxolan-2-yl) phenoxy) phthalonitrile (1). The new compounds have been characterized by the combination of FT-IR, H-1 NMR, UV-Vis, Mass spectra and elemental analysis. Compound 1 crystallizes in the Orthorhombic, space group Pbca with a = 9.2542 (4) , b = 13.3299 (5) , c = 23.2333 (11) , and Z = 8. Compound 1 is built up from two planar groups (phthalonitrile and phenoxy), with a dihedral angle of 69.693(36)A degrees between them and non-planar dioxolane group. We report a combined experimental and theoretical study on molecule 1, as well. Geometric, spectroscopic and electronic properties of compound 1 has been calculated using B3LYP method and 6-311++G(dp) basis set. Fluorescence spectroscopy was applied to record the photoluminescence spectra of the prepared phthalocyanines and the photophysical and photochemical properties were examined in DMSO.