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Synthesis and characterization of novel metal-free and metallophthalocyanines peripherally fused to four 24-membered tetraoxatetraaza macrocycles

S. ZEKİ YILDIZ

Department of Chemistry, Karadeniz Technical University, 61080 Trabzon, Turkey

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HALTİ KANTEKİN

Department of Chemistry, Karadeniz Technical University, 61080 Trabzon, Turkey

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, and

YAŞAR GÖK

Department of Chemistry, Karadeniz Technical University, 61080 Trabzon, Turkey

Corresponding author, Department of Chemistry, Karadeniz Technical University, 61080 Trabzon, Turkey.

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https://doi.org/10.1002/jpp.291Cited by:18 (Source: Crossref)

Abstract

New metal-free 5 and metallophthalocyanines 6-11(M = Cu, Ni, Co, Pb, Zn) fused in peripheral positions with four 24-membered tetraoxatetraaza macrocycles were prepared by cyclotetramerization of 24,25-dicyano-4,10,13,17-tetra(toluene-p-sulfonyl)-1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22-didicontinehydrobenzo[y][3,9,12,18]tetraaza[1,7,16,22]tetraoxatetradicontine in the presence of the corresponding metal salt or a strong organic base. While the N-tosylated derivatives of the phthalocyanines are soluble in common organic solvents, the detosylated derivative of copper phthalocyaninate is soluble in water. The aggregation properties of the phthalocyanines were also investigated as a function of concentration, solvent and oxidative medium. The new compounds are characterized by a combination of elemental analysis and ¹H NMR, ¹³C NMR, IR, UV-vis and MS spectral data.

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