Synthesis and properties of axially BODIPY conjugated subphthalocyanine dyads

Abstract

The treatment of boron(III) subphthalocyanine chloride with borondipyrromethene derivatives containing either one or two [4-(N,N-dimethylamino)phenyl]ethenyl groups in toluene gave the corresponding axially substituted boron(III) subphthalocyanine dyes. The novel borondipyrrornethene-subphthalocyanine dyes were fully characterized by mass spectrometry, UV-Vis, H-1 and C-13 NMR spectroscopy as well as elemental analysis. The photophysical properties of title compounds were investigated by means of absorption and fluorescence spectroscopy in dilute benzene solutions. The new dyads exhibited a highly efficient energy transfer process from the excited subphthalocyanine unit to the borondipyrromethene unit. The singlet oxygen generation ability of these dyads was also investigated in dimethylsulfoxide for determination of possibility of these compounds for photodynamic therapy of cancer. (C) 2013 Elsevier Ltd. All rights reserved.