Studies on Phosphorus Phthalocyanines and Triazatetrabenzcorroles

Li, Junzhong; Subramanian, L. R.; Hanack, Michael

doi:10.1002/(sici)1099-0690(199812)1998:12<2759::aid-ejoc2759>3.0.co;2-9

Cited by 66 publications

(42 citation statements)

References 35 publications

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“…The radius of divalent lead ions (1.75Å) is greater than the radius of the inner core of the phthalocyanine ring, so the metal ion does not fit inside the central cavity but it lies above the phthalocyanine plane. Therefore these compounds could show anomalous redox behaviour [20][21][22][23][24]. Since the metal sits outside of the phthalocyanine ring, the complex shows a tendency to demetallation in the redox reactions [24].…”

Section: Introductionmentioning

confidence: 99%

Spectroelectrochemical characterization and controlled potential chronocoulometric demetallation of tetra- and octa-substituted lead phthalocyanines

Koca

Dinçer

Çerlek

et al. 2006

Electrochimica Acta

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Section: Introductionmentioning

confidence: 99%

Spectroelectrochemical characterization and controlled potential chronocoulometric demetallation of tetra- and octa-substituted lead phthalocyanines

Koca

Dinçer

Çerlek

et al. 2006

Electrochimica Acta

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“…[7]. Later we encountered the tetrabenzocorroles in the reaction of substituted and unsubstituted PcH 2 with PBr 3 [9]. We are not going to delve into the detailed explanation of the characterization of tetrabenzocorroles in the reactions described above; suffice it to say that tetrabenzocorroles are established compounds long known in the literature.…”

mentioning

confidence: 99%

Phthalocyanine dimer with a direct Si—Si linkage: A response to a recent work

Subramanian

Hanack

2000

J. Porphyrins Phthalocyanines

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“…7 For example, an increase in the length of the substituent in the macroligand by one The absence of one meso nitrogen atom in triaza tetrabenzocorrole compared to phthalocyanine results in a substantial change in the electronic absorption spec trum characterized by the split Q band and the Soret band, whose intensity is almost twice as high as that of the Q band (Fig. 1, b).…”

Section: Resultsmentioning

confidence: 90%

Synthesis of alkyl-substituted phosphorus phthalocyanines and triazatetrabenzocorroles

2007

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New alkyl substituted phosphorus phthalocyanines and triazatetrabenzocorroles were syn thesized. The structures of these complexes were confirmed by 1 H, 13 C, and 31 P NMR spec troscopy, mass spectrometry, and electronic absorption spectroscopy.Methods for the synthesis and properties of various metal phthalocyanines having both planar and sandwich structures have been studied in sufficient detail, whereas phthalocyanine complexes with nonmetals have received much less attention. In our previous study, 1 we have in vestigated boron phthalocyanine complexes. Due to the small radius, boron is prone to form only subphthalo cyanine complexes with ligands consisting of three iso indole fragments. Due to the geometric and electronic structures, these complexes exhibit unusual spectroscopic properties allowing their use in new fields of engineering.The aim of the present study was to synthesize alkyl substituted phosphorus phthalocyanines and triazatetra benzocorroles and investigate their spectroscopic prop erties.Phosphorus phthalocyanines were synthesized for the first time 2 in 1981. However, data on these compounds are scarce, and many questions remain open.It was reported that phosphorus can form not only phthalocyanine complexes but also complexes with tri azatetrabenzocorroles. 3,4 Initially, it has been hypoth esized that the latter compounds are phthalocyanine com plexes of trivalent phosphorus. 2 However, further physi cochemical studies showed that the complex consists of triazatetrabenzocorrole and pentavalent phosphorus; ana logs of this complex are synthesized for both nonmetals (germanium and silicon) and some metals (manganese, iron, and chromium). 5 The electronic structure of tri azatetrabenzocorrole, whose "window" radius allows sta bilization of the complexing ions in high oxidation states, can favor the use of these compounds in oxidative ca talysis. Results and DiscussionWe used metal free phthalocyanines 1 and 2, which have been prepared in our earlier study, 6 as the starting compounds for the synthesis of phosphorus phthalocya nine and triazatetrabenzocorrole complexes, respectively. Depending on the nature of the starting phosphorus con taining compound, the reactions give different types of complexes. The reactions of phosphorus(v) oxyhalides produce phthalocyanine complexes, whereas the reac tions of phosphorus(III) bromide give triazatetrabenzo corroles (Scheme 1).In the reaction with PBr 3 for 1.5 h, phthalocyanine 1 undergoes complete conversion to form the only product of the phthalocyanine nature, viz., triazatetrabenzocor role (3). Since compound 3 is poorly soluble in most of organic solvents, investigations of 3 present difficulties. The use of tert butyl substituted phthalocyanine (2) as the starting compound allowed us to substantially increase the solubility of the resulting triazatetrabenzocorrole 4.The reaction of phthalocyanine 2 with POCl 3 giving rise to compound 6 was completed in 24 h. The yield of the product was 62%. The reaction time in the case of POBr 3 decreases to 4...

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Studies on Phosphorus Phthalocyanines and Triazatetrabenzcorroles

Cited by 66 publications

References 35 publications

Spectroelectrochemical characterization and controlled potential chronocoulometric demetallation of tetra- and octa-substituted lead phthalocyanines

Spectroelectrochemical characterization and controlled potential chronocoulometric demetallation of tetra- and octa-substituted lead phthalocyanines

Phthalocyanine dimer with a direct Si—Si linkage: A response to a recent work

Synthesis of alkyl-substituted phosphorus phthalocyanines and triazatetrabenzocorroles

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