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

Sevim A. M., Yuzeroglu M., Gül A.

MONATSHEFTE FUR CHEMIE, cilt.151, sa.7, ss.1059-1068, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 151 Sayı: 7
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1007/s00706-020-02639-w
  • Dergi Adı: MONATSHEFTE FUR CHEMIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1059-1068
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

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.