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Open AccessArticle

Novel Hexadeca-Substituted Metal Free and Zinc(II) Phthalocyanines; Design, Synthesis and Photophysicochemical Properties

1
Department of Chemistry, Taibah University, Al-Madinah Al Munawrah, P.O. Box 344, Saudi Arabia
2
Department of Chemistry, Gebze Technical University, 41400 Gebze, Kocaeli, Turkey
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(1), 77; https://doi.org/10.3390/molecules24010077
Received: 4 November 2018 / Revised: 20 December 2018 / Accepted: 21 December 2018 / Published: 26 December 2018
The syntheses of a novel 1,4,8,11,15,18,22,25-octahexyloxy-2,3,9,10,16,17,23,24-octa-(4-trifluoromethoxyphenyl) phthalocyanine (3a) and its zinc(II) phthalocyanine derivative (3b) have been described and characterized by elemental analysis,1H NMR, 13C NMR, 19F NMR, mass, UV-Vis and FT-IR. The newly prepared metal-free phthalocyanine and its zinc(II) counterpart are soluble in most organic solvents. The photophysical and photochemical properties such as aggregation, fluorescence, singlet oxygen generation and photodegradation under light irradiation of these phthalocyanines have been investigated in DMF. The hexadeca-substituted phthalocyanines (3a and 3b) showed longer absorption and emission wavelength values when compared to that of reported phthalocyanine derivatives due to substitution of the all possible positions in the phthalocyanine framework. The zinc(II) phthalocyanine derivative does not only have a good singlet oxygen generation but also has other photophysicochemical properties that enables this phthalocyanine to be useful as a photosensitizer for cancer treatment using photodynamic therapy. View Full-Text
Keywords: phthalocyanine; Suzuki-coupling; photophysical; photochemical; photodynamic therapy phthalocyanine; Suzuki-coupling; photophysical; photochemical; photodynamic therapy
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MDPI and ACS Style

Awaji, A.I.; Köksoy, B.; Durmuş, M.; Aljuhani, A.; Alraqa, S.Y. Novel Hexadeca-Substituted Metal Free and Zinc(II) Phthalocyanines; Design, Synthesis and Photophysicochemical Properties. Molecules 2019, 24, 77.

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