Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents

Sevim A. M., Yuzeroglu M., Gül A.

MONATSHEFTE FUR CHEMIE, vol.151, no.7, pp.1059-1068, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 151 Issue: 7
  • Publication Date: 2020
  • Doi Number: 10.1007/s00706-020-02639-w
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1059-1068
  • Istanbul Technical University Affiliated: Yes


Novel metallophthalocyanines substituted with four peripheral 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy groups were prepared by Schiff base condensation of 4-aminophenoxy-substituted phthalocyanines with 3,4-bis(benzyloxy)benzaldehyde. The structures were elucidated with elemental analysis, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectrometry, and matrix assisted laser desorption ionization-time of flight spectrometry along with Ultraviolet-Visible spectrophotometry. In the studied concentration range of 1-10 x 10(-6) M, no appreciable aggregation of the new species was detected. In tetrahydrofuran, the fluorescent quantum yield phi(F)value of the zinc phthalocyanine was lower than the unsubstituted ZnPc (phi(F) = 0.25) due to the peripheral [3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents which surely caused fluorescence quenching. The zinc phthalocyanine showed fluorescent quenching by the addition of 1,4-benzoquinone in tetrahydrofuran with obedience to Stern-Volmer kinetics.