Highly Organosoluble Metal‐Free Phthalocyanines and Metallophthalocyanines: Synthesis and Characterization

Abstract

The syntheses and characterization of metal-free and metalcontaining (Zn and Ni) derivatives of a symmetrically octasubstituted phthalocyanine derived from 4,5:12,13-bis(4Ј-tert-butylbenzo) -8,9-(4ЈЈ,5ЈЈ-dicyanobenzo)-6,11-ditosyl-6,11-diaza-2,15-dithiacyclohexadeca-4,8,12-triene and CuPc from 4,5:12,13-bis(4Ј-tert-butylbenzo)-8,9-(4ЈЈ,5ЈЈ-dibromobenzo)-6,11-ditosyl-6,11-diaza-2,15-dithiacyclohexadeca-4,8,12-triene were carried out. Pentanuclear silver(I) and palladium(II) complexes have also been prepared from nickel(II) phthalocyaninate derivatives. The prepared phthalocyanines were semiconducting materials in the range of 10 -5 to

Novel porphyrazines containing peripherally functionalized macrocyclic (N2O2, N2S2) units: Synthesis and characterization

“…Our previous papers have described a series of phthalocyanines with various functional groups. These phthalocyanines have N-, Oand S-containing functionalities such as diazadioxa [25], cryptand [26,27], crown ether fused diloop [28], diazadithia macrocyclic with tert-butyl [29], and tetrathiamonoaza macrocyclic [30]. The immediate consequences of these peripheral substituents are enhanced solubility in common organic solvents and additional donor sites for alkali or transition metal ions.…”

Synthesis, spectroscopic and DFT Characterization of 4β-(4-tert-Butylphenoxy)phthalocyanine positional isomers for non-linear optical absorption

“…When interacting with strong electromagnetic fields such as laser radiation, the highly conjugated Pc structure promotes preferable polarizability and as well as fast distribution charge. 6 Phthalocyanines are optical limiters that display reverse saturable absorption (RSA). 7,8 This mechanism involves a sequential two photon absorption from the ground state (S 0 ) to a higher excited state (S 1 ).…”

“…When peripheral substituents are considered, a condensation reaction with a single phthalonitrile precursor can result in four constitutional isomers with C s , C 2v , C 4h and D 2h symmetries. 6 Symmetry has been found to influence the NLO properties of Pcs. 5 It has been reported that Pcs of lower symmetry show greater optical properties compared to Pcs of higher symmetry.…”

Microwave-assisted synthesis and characterization of phthalocyanines substituted with azo compound containing eugenol moiety

“…The most important industrial application of phthalocyanines is the formation of color complexes with metal cations that are used as highly stable pigments and dyes [2]. In addition, they can find commercial applications as: photovoltaic materials in solar cells [3e5], systems for fabrication of light emitting diodes (LED) [6,7], liquid crystalline [8], and non-linear optical materials [9,10], sensitizers for photodynamic (PDT) cancer therapy [11,12], photoconductors in xerography [13], dyes at recording layers for CD-R and DVD-R optical storage discs [14], as well as diverse catalytic systems [15,16]. Phthalocyanines are usually prepared by the high temperature cyclotetramerization processes of either phthalonitrile or phthalic anhydride, in which the template effect afforded by a suitable metal cation is required.…”