meso-tetraalkyltetrabenzoporphyrins and their zinc complexes. Synthesis and properties

Yakubov, L. A.; Galanin, N. Е.; Shaposhnikov, G. P.; Lebedevа, N. Sh.; Mal’kova, E. A.

doi:10.1134/s1070363208060273

Cited by 2 publications

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“…The elemental composition of the product corresponded to the formula C 36 H 23 N 3 Zn. These findings led us to presume that the isolated compound has the structure of 4,5 : 9,10 : 14,15 : 19,20-tetrabenzo-21,22,23-triazatetracyclo[16.2.1.1 3,6 .1 8,11 ]tricosa-1,3,5,7,9,11,13,15,-17,19-decaene zinc complex (II), which was formed according to Scheme 1.…”

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confidence: 95%

“…By reaction of meso-tetramethyltetrabenzoporphyrinatozinc(II) (VII) with sodium nitrite under analogous conditions we obtained 4,5 : 9,10 : 14,15 : 19,20-tetrabenzo-2,7,12,17-tetramethyl-21,22,23-triazatetracyclo[16.2.1.1 3,6 .1 8,11 ]tricosa-1,3,5,7,9,11,13,15,17,19-decaene zinc complex (VIII). Compound VIII was isolated a dark green powder, which is soluble in benzene, chloroform, acetone, and DMF.…”

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confidence: 98%

“…Therefore, nitrosation at the nitrogen atom becomes possible. N-Nitroso derivative IV thus formed loses N 2 O molecule (thermodynamically favorable process), and unstable triradical cation V immediately takes up three protons and is reduced to 4,5 : 9,10 : 14,-15:19,20-tetrabenzo-21,22,23-triazatetracyclo-[16.2.1.1 3,6 .1 8,11 ]tricosa-1,3(23),5,7,9,11,13,15,17,19-DOI: 10.1134/S1070428010100234 Scheme 1. decaene zinc complex (VI) which is tautomeric to compound II. The latter was isolated as a dark green substance, which is soluble in benzene, chloroform, acetone, and DMF, and insoluble in water and aqueous acids and bases.…”

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confidence: 99%

“…Considerable broadening of the Soret band should also be noted, which may be due to association of compound VIII in weakly polar solvents. Tetrabenzoporphyrinatozinc(II) (I) was synthesized according to the procedure described in [10], and meso-tetramethyltetrabenzoporphyrinatozinc(II) (VII) was prepared as reported in [11]. 1.1 3,6 .1 8,11 ]tricosa-1,3,5,7,9,11,13,-15,17,19-decaene and 4,5:9,10:14,15:19,20-tetrabenzo-2,7,12,17-tetramethyl-21,22,23-triazatetracyclo[16.2.1.1 3,6 .1 8,11 ]tricosa-1,3,5,7,9,11,13,15,17,19decaene zinc complexes II and VIII (general procedure).…”

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confidence: 99%

“…Mass spectrum of 4,5 : 9,10 : 14,15 : 19,20-tetrabenzo-2 , 7, 1 2, 1 7 -t e t r a m e t hy l -2 1, 2 2 , 2 3-t ria z a t e t ra c y c l o -[16.2.1.1 3,6 .18,11 ]tricosa-1,3,5,7,9,11,13,15,17,19-decaene zinc complex (VIII). on a Bruker Reflex III mass spectrometer.…”

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Unusual Reaction of Tetrabenzoporphyrin and meso-Tetramethyltetrabenzoporphyrin Zinc Complexes with Sodium Nitrite in Acid Medium

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Unusual Reaction of Tetrabenzoporphyrin and meso-Tetramethyltetrabenzoporphyrin Zinc Complexes with Sodium Nitrite in Acid Medium

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Phthalocyanine Analogues: Unexpectedly Facile Access to Non‐Peripherally Substituted Octaalkyl Tetrabenzotriazaporphyrins, Tetrabenzodiazaporphyrins, Tetrabenzomonoazaporphyrins and Tetrabenzoporphyrins

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et al. 2011

Chemistry A European J

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Controlled syntheses of phthalocyanine/benzoporphyrin hybrid structures have been achieved. We report a simple means for obtaining non-peripherally octaalkyl-substituted derivatives of tetrabenzotriazaporphyrin (TBTAP), tetrabenzodiazaporphyrin (TBDAP), tetrabenzomonoazaporphyrin (TBMAP) and tetrabenzoporphyrin (TBP) macrocycles by treating 3,6-dialkyl phthalonitriles with differing amounts of the Grignard reagent MeMgBr. This range of macrocyclic products is not obtained from corresponding reactions of a Grignard reagent with 4-substituted phthalonitriles, reported previously, or reaction of MeMgBr with a 4,5-dialkyl phthalonitrile. Attempts to form a meso-substituted TBTAP from 3,6-dialkyl phthalonitriles by reaction with benzyl and long-chain alkyl Grignard reagents unexpectedly gave only the parent macrocycle unsubstituted at the meso position. The synthetic protocols are by far the most straightforward and convenient means to access these interesting, but scarcely studied, classes of material. The new series of substituted macrocyclic compounds, obtained as the metal-free and magnesium- and copper(II)-metallated derivatives, show trends in the UV/Vis spectra consistent with those predicted elsewhere by Kobayashi. Characterisation of the new families allows further trends to be identified as meso-nitrogen atoms are sequentially replaced by methine bridges, for example, the compounds provide novel examples of macrocyclic structures that show columnar mesophase behaviour. Single-crystal X-ray structure determinations have been obtained for three magnesium-metallated derivatives bearing eight hexyl substituents and constitute the first set of structural data obtained for such a series.

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meso-tetraalkyltetrabenzoporphyrins and their zinc complexes. Synthesis and properties

Cited by 2 publications

References 2 publications

Unusual Reaction of Tetrabenzoporphyrin and meso-Tetramethyltetrabenzoporphyrin Zinc Complexes with Sodium Nitrite in Acid Medium

Unusual Reaction of Tetrabenzoporphyrin and meso-Tetramethyltetrabenzoporphyrin Zinc Complexes with Sodium Nitrite in Acid Medium

Phthalocyanine Analogues: Unexpectedly Facile Access to Non‐Peripherally Substituted Octaalkyl Tetrabenzotriazaporphyrins, Tetrabenzodiazaporphyrins, Tetrabenzomonoazaporphyrins and Tetrabenzoporphyrins

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