147699-63-6

Upstream product

• 139152-08-2 4,5-dichlorophthalonitrile 
• 108-95-2 phenol 
• 942-06-3 4,5-dichlorophthalic anhydride 
• 56962-08-4 4,5-dichlorophthalic acid 
• 329326-22-9 5-nitro-4-phenoxyphthalodinitrile 
• 206268-72-6 4-bromo-5-nitrophthalonitrile 
• 38791-62-7 4-phenoxyphthalonitrile 
• 31643-49-9 4-Nitrophthalonitrile 
• 147699-62-5 4,5-dichloro-1,2-benzenedicarboxamide 
• 15997-89-4 4,5-dichlorophthalimide 

Downstream Products

• 1201810-24-3 4,5-bis(p-chlorosulfonylphenoxy)phthalonitrile 
• 60387-48-6 2,3,9,10,16,17,23,24-octa-phenylphthalocyanine 

Relevant academic research and scientific papers

Synthesis and structural characterization of Cr(III) complex of porphyrazine and phthalocyanine derivatives: Kinetic studies of metalation and redox activity

Chromium(III) complexes of 2,3,7,8,12,13,17,18-octakis(propyl)porphyrazine and 2,3,9,10,16,17,23,24-octa substituted phthalocyanine were synthesized, characterized and the kinetics of metalation and redox activity studied and reported. The results obtained indicated that the rate of incorporation of Cr(III) into the central cavity of the ligands is a function of the kinetic inertness and size of the metal ion as well as the peripheral substituents of the ligand. The Cr(III) complex of 2,3,7,8,12,13,17,18-octakis(propyl)porphyrazine exhibited a metal based reduction. Hence it was concluded that the nature of the incorporated metal ions has an influence on the rate and mechanism of incorporation of the metal ion and also the redox activities of these complexes.

Synthesis and association in dichloromethane solution of low-symmetry phenoxy(fluoro)-substituted nickel phthalocyaninates

Cross-condensation of 4,5-diphenoxyphthalonitrile (component A) with tetrafluorophthalonitrile (component B) in the presence of nickel(II) acetate has yielded the low-symmetry nickel phthalocyaninates of the A3B, ABAB, and AABB types. Their spe

Complementary Syntheses Giving Access to a Full Suite of Differentially Substituted Phthalocyanine-Porphyrin Hybrids

Phthalocyanines and porphyrins are often the scaffolds of choice for use in widespread applications. Synthetic advances allow bespoke derivatives to be made, tailoring their properties. The selective synthesis of unsymmetrical systems, particularly phthalocyanines, has remained a significant unmet challenge. Porphyrin-phthalocyanine hybrids offer the potential to combine the favorable features of both parent structures, but again synthetic strategies are poorly developed. Here we demonstrate strategies that give straightforward, controlled access to differentially substituted meso-aryl-tetrabenzotriazaporphyrins by reaction between an aryl-aminoisoindolene (A) initiator and a complementary phthalonitrile (B). The choice of precursors and reaction conditions allows selective preparation of 1:3 Ar-ABBB and, uniquely, 2:2 Ar-ABBA functionalized hybrids.

Palladium(II) octaalkoxy- and octaphenoxyphthalocyanines: Synthesis and evaluation as catalysts in the Sonogashira reaction

Octaalkoxy- and octaphenoxysubstituted palladium phthalocyanines were used as a new family members of cross-coupling catalysts in the Sonogashira reaction. For the first time it was shown that terminal alkynes reacted mildly with p-substituted aryl bromides in gently conditions at room temperature under Pd and Cu-cocatalysis to give the corresponding phenylacetylenes. This protocol represents the use of palladium phthalocyanines as homogeneous catalysts in the Pd/Cu-promoted Sonogashira reaction.

Synthesis of Magnesium Octa-4,5-phenoxyphthalocyanine and Sulfo- and Alkylsulfamoyl Derivatives on Its Basis

By the reaction of nucleophilic substitution of bromine atom and the nitro group of 4-bromo-5- nitrophthalonitrile 4,5-diphenoxyphthalonitrile was obtained and on its basis new derivatives of octa-4,5- phenoxyphthalocyanine were synthesized soluble in wat

Flying-seed-like liquid crystals. Part 4: A novel series of bulky substituents inducing mesomorphism instead of using long alkyl chains

We synthesized a novel series of flying-seed-like derivatives (3a-g) based on phthalocyaninato copper(ii) (abbreviated as PcCu) substituted by bulky groups {PhO (a), (o-C1)PhO (b), (m-C1)PhO (c), (p-C1)PhO (d), [m,p-(C1)2]PhO (e), [m,m′-(C1)2]PhO (f), and [m,p,m′-(C1)3]PhO (g)} instead of using long alkyl chains, in order to investigate their mesomorphism. Their phase transition behaviour and the mesophase structures were established using a polarizing optical microscope, a differential scanning calorimeter, a thermogravimetry analyser and a temperature-dependent small angle X-ray diffractometer. It was demonstrated that (PhO)8PcCu (3a) and [(p-C1)PhO]8PcCu (3d) show no mesophase, whereas [(m-C1)PhO]8PcCu (3c), {[m,p-(C1)2]PhO}8PcCu (3e), {[m,m′-(C1)2]PhO}8PcCu (3f), and {[m,p,m′-(C1)3]PhO}8PcCu (3g) show various kinds of columnar mesophases of Colro(P21/a), Colro(P21/a), Colro(C2/m) and Coltet.o, respectively, while [(o-C1)PhO]8PcCu (3b) shows a monotropic Colro(P2m) mesophase. Thus, we revealed that mesomorphism could be induced by these novel bulky substituents instead of using long alkyl chains, and that the mesophase structures were greatly affected by the number and position of the methoxy groups. In particular, it is very interesting that the derivatives with methoxy group(s) at the meta position(s), namely, 3c, 3e, 3f and 3g, tend to show enantiotropic mesophase(s), whereas neither the derivative with no methoxy group, 3a, nor the derivative with a methoxy group at the para position, 3d, show a mesophase. This journal is

Synthesis and high ranked NLT properties of new sulfonamide-substituted indium phthalocyanines

The synthesis and characterization of three new indium phthalocyanines bearing eight N-alkyl- or N-arylsulfonamide groups is described. The new compounds are {2,3,9,10,16,17,23,24-octakis[4-(4-methoxyphenylaminosulfonyl] phenoxy]phthalocyaninato}indium(III) chloride (7), {2,3,9,10,16,17,23,24- octakis[4-diethylaminosulfonyl)phenoxy]phthalocyaninato}indium(III) chloride (8) and {2,3,9,10,16,17,23,24-octakis[4-didodecylaminosulfonyl)phenoxy] phthalocyaninato}indium(III) chloride (9), and were obtained in 23-49% yields. The precursors of phthalocyanines 7-9 are sulfonamide-substituted phthalonitriles that can be prepared by reacting 4,5-bis(4- chlorosulfonylphenoxy)phthalonitrile (3) with amines. The nonlinear transmission (NLT) of complexes 7-9 was determined at 532 nm using ns pulses. All three phthalocyanines behave as reverse saturable absorbers with increasing efficiency of optical limiting in the order 7 8 9. A comparative analysis of the NLT results is attempted in terms of the structural differences in 7-9.

Synthesis of sulfonamide-substituted phthalocyanines

The synthesis and characterization of new phthalocyanines bearing eight N-alkyl or N-aryl sulfonamide groups is described. The synthetic route involves the chorosulfonation of 4,5-diphenoxyphthalonitrile with chlorosulfonic acid and reaction of the resulting 4,5-bis(p-chlorosulfonylphenoxy)phthalonitrile with amines. The sulfonamide-substituted phthalonitriles are then cyclotetramerized to yield the title compounds in good yields (50-83%).

Phthalocyanine synthesis in ionic liquids: Preparation of differently substituted phthalocyanines in tetrabutylammonium bromide

A series of alkylthio, alkoxy, and phenoxy phthalonitriles have been prepared by nucleophilic substitution reactions on suitable phthalonitrile precursors in molten tetrabutylammonium bromide. This readily available and inexpensive ionic liquid can also b

Novel nitrogen-containing heteroaryl compounds and methods of use thereof

The present invention relates to compounds suitable for use in mediating hypoxia inducible factor and for treating erythropoietin-associated conditions by increasing endogenous erythropoietin in vitro and in vivo.