Novel metal(III) and metal free soft phthalocyanine metal ion sensors bearing (1-hydroxyhexan-3-ylthio)-substituents: Synthesis, characterization, aggregation behavior

A new substituted phthalonitrile derivative, 4-(1-hydroxyhexan-3-ylthio) phthalonitrile, was prepared by the nucleophilic displacement reaction between 1-hydroxyhexan-3-ylthio and 4-nitrophthalonitrile. The highly soluble novel metallo phthalocyanines [M: 2H (2), Ga(III) (3), In(111) (4)] with four peripheral 1-hydroxyhexan-3-ylthio groups were synthesized by cyclotetramerization. Purification of these compounds was tedious because of their high solubility and they were purified by column chromatography. They were characterized by elemental analysis, FTIR, H-1 and C-13 NMR, MALDI-TOF and UV-Vis spectral data. The complexes were soluble in both polar solvents and non-polar solvents, such as MeOH, EtOH, CHCl3, CH2Cl2, benzene, toluene and even hexane. Absorption spectral changes of the functional MPcs during addition of Ag(I) and Pd(II) soft-metal ions were evaluated by UV-Vis spectroscopy, with monomer-dimer formation. (C) 2014 Elsevier Ltd. All rights reserved.