Recent advances in chemistry of phthalocyanines, bearing electron-withdrawing halogen, nitro and N-substituted imide functional groups, prospects for their practical application
Overview on approaches to the synthesis of phthalocyanines, bearing electron-withdrawing halogen-, nitro- and N-substituted imide functional groups in different positions of the phthalocyanine macrocycle is presented. Some approaches to corresponding substituted phthalonitriles are also covered. Review includes unusual techniques of synthesis of phthalocyanines, like a microwave assisted approaches, synthesis in the medium of ionic liquids and method of synthesis in mild conditions based on double-addition of oximes. Synthesis, optical and magnetic peculiarities of surprizingly stable anionic forms of double-decker phthalocyanine complexes with electron-withdrawing substituents was highlighted. Various application areas for phthalocyanines with electron-withdrawing functional groups (optical limiters, gas sensors, organic thin-film transistors, memory elements, single-molecule magnets, application in medicinal chemistry), as well as preparation of hybrid nanoparticles coated by phthalocyanine shell are covered.