Gallium chloride phthalocyanines possessing 4-(trifluoromethoxy)phenoxy units: Synthesis, characterization, and photophysicochemical investigations

Farajzadeh N., Atmaca G. Y., Cinar M. E., ERDOĞMUŞ A., Kocak M. B.

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol.68, no.8, pp.1466-1477, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 68 Issue: 8
  • Publication Date: 2021
  • Doi Number: 10.1002/jccs.202000497
  • Journal Name: JOURNAL OF THE CHINESE CHEMICAL SOCIETY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, CAB Abstracts, Chemical Abstracts Core, INSPEC
  • Page Numbers: pp.1466-1477
  • Keywords: aggregation, DFT, non&#8208, peripheral, photophysicochemistry, phthalocyanine, SUBSTITUTED ZINC PHTHALOCYANINES, PHOTOCHEMICAL PROPERTIES, ELECTRONIC-PROPERTIES, DFT CALCULATIONS, PHENOXY, SPECTRA, TETRA, SEPARATION, MOLECULES, CHEMISTRY
  • Yıldız Technical University Affiliated: Yes

Abstract

This study reports synthesis of three new metallophthalocyanines namely 1(4),8(11),15(18),22(25)-tetrakis-(4-(trifluoromethoxy)phenoxy) phthalocyaninato} Gallium chloride (1-Ga), {2(3),9(10),16(17),23(24)-tetrakis-(4-(trifluoromethoxy)phenoxy)phthalocyaninato} Gallium chloride (2-Ga), and {2,3,9,10,17,18,23,24-octakis-(4-(trifluoromethoxy)phenoxy)phthalocyaninato} Gallium chloride (3-Ga). The newly synthesized macromolecules were characterized using different spectroscopic approaches, such as Fourier-transform infrared (FT-IR), ultraviolet-visible (UV-vis), and mass (MS) spectroscopy. Aggregation properties of the resulting compounds were studied at different concentrations ranging from 4 x 10(-6) to 14 x 10(-6) M. Density functional theory level computations were conducted to shed light on their electronic properties. The effect of the number and position of the substituent on photophysicochemical properties of the gallium chloride complexes (1-Ga, 2-Ga, and 3-Ga) was studied for the examination of their performance as photosensitizer candidates in photodynamic therapy (PDT), comparatively. The complex 3-Ga shows up the highest singlet oxygen quantum yield (phi(Delta) = 0.87). The photophysical and photochemical features of the stated compounds are useful for PDT applications.