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 THE at reflux in the presence of molecular sieves. The new compounds were characterized by using elemental analyses, FT-IR, UV-vis, H-1 NMR, F-19 NMR, B-11 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. (C) 2016 Elsevier B.V. All rights reserved.