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Phthalonitriles and metal-free phthalocyanines substituted with 2,3-dihydroxypropoxy and [2,3,5,6-tetrafluoro-4-(2,3-dihydroxypropoxy)]benzyloxy groups were synthesized. Their complexes with phenylboronic acid were prepared in THF at reflux in the presence of molecular sieves. The new compounds were characterized by using elemental analyses, FT-IR, UV–vis, 1 H NMR, 19 F NMR, 11 B NMR, and MALDI-TOF MS spectral data. Aggregation tendency of phthalocyanine complexes in relation to their concentrations were investigated by changes in their absorption spectra. Furthermore, photophysical and photochemical properties of metal-free phthalocyanines were investigated in ethanol and dichloromethane. The fluorescence quenching properties of synthesized phthalocyanines were investigated using 1,4-benzoquinone in dichloromethane. [ABSTRACT FROM AUTHOR]

Highlights: [•] Novel phthalocyanines with four 9-anthracenylmethyl esters have been prepared. [•] Aggregation tendency vs. concentration and solvent polarity has been tested. [•] Photophysical properties of novel phthalocyanine compounds have been investigated. [•] The energy transfer between anthracene substituents and Pc core was examined. [ABSTRACT FROM AUTHOR]