Synthesis, characterization, electrical and dielectric permittivity measurements of 2,9,16,23-tetra(4-ferrocenylimino-3-nitrophenoxy)phthalocyanines

Ümit Salan, Ahmet Altindal, Mustafa Bulut, Özer Bekaroǧlu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


2,9,16,23-tetra(4-amino-3-nitrophenoxy)phthalocyanines were synthesized from 4-(4-amino-3-nitrophenoxy)phthalonitrile which was obtained from 4-nitro-1,2-dicyanobenzene and 4-amino-3-nitrophenol. 2,9,16,23-tetra(4- ferrocenylimino-3-nitrophenoxy)phthalocyanine and 2,9,16, 23-tetra(4- ferrocenylimino-3-nitrophenoxy)phthalocyaninatocobalt(II) were synthesized in a one-step condensation reaction of ferrocenylaldehyde with 2,9,16,23-tetra(4- amino-3-nitrophenoxy)phthalocyanine and 2,9,16,23-tetra(4-amino-3-nitrophenoxy) phthalocyaninatocobalt(II), respectively. The novel compounds were characterized by elemental analysis, Inductively Coupled Plasma (ICP-MS), UV-vis, IR and 1H NMR spectroscopy. The effects of temperature and frequency on the conduction properties (a.c. and d.c.) and the dielectric constant were studied on pellet samples of 2,9,16,23-tetra(4-amino-3-nitrophenoxy)phthalocyanine, 2,9,16,23-tetra(4-ferrocenylimino-3-nitrophenoxy)phthalocyanine, 2,9, 16,23-tetra(4-amino-3-nitrophenoxy)phthalocyaninatocobalt(II) and 2,9,16,23-tetra(4-ferrocenylimino-3-nitrophenoxy)phthalocyaninatocobalt(II), with evaporated, ohmic gold electrodes in the frequency range 40-105 Hz. and within the temperature range 290-400 K. Unlike many metallophthalocyanines, a variable-range hopping model is found to most appropriately fit the experimental conductivity data of 2,9,16,23-tetra(4- ferrocenylimino-3-nitrophenoxy)phthalocyanine and 2,9,16,23-tetra(4-ferrocenyl- imino-3-nitrophenoxy)phthalocyaninatocobalt(II), while for 2,9,16,23-tetra(4- amino-3-nitrophenoxy)-phthalocyanine and 2,9,16,23-tetra(4-amino-3-nitrophenoxy) phthalocyaninatocobalt(II), thermally activated conduction with single activation energy is valid. Frequency and temperature dependence of the a.c conductivity were analyzed in terms of existing theory for 2,9,16,23-tetra-(4- amino-3-nitrophenoxy)phthalocyanine, 2,9,16,23-tetra(4-ferrocenylimino-3- nitrophenoxy)phthalocyanine, 2,9,16,23-tetra(4-amino-3-nitrophenoxy) phthalocyaninatocobalt(II) and 2,9,16,23-tetra(4-ferrocenylimino-3-nitrophenoxy) phthalocyaninatocobalt(II). It was found that the a.c. conductivity of the compounds depends on the frequency, obeying the empirical formula, σac = A(T)ωs, The model parameters calculated are reasonable and consistent with the prediction of the correlated barrier hopping model for 2,9,16,23-tetra(4-ferrocenylimino-3-nitrophenoxy) phthalocyanine and 2,9,16,23-tetra(4-ferrocenylimino-3-nitrophenoxy) phthalocyaninatocobalt(II) and the quantum mechanical tunneling model for 2,9,16,23-tetra(4-amino-3-nitrophenoxy)phthalocyanine and 2,9,16,23-tetra(4- amino-3-nitrophenoxy)phthalocyaninatocobalt(II). The dielectric constant of the compounds increased with temperature and decreased with frequency in the investigated range.

Original languageEnglish
Pages (from-to)1263-1270
Number of pages8
JournalJournal of Porphyrins and Phthalocyanines
Issue number11
Publication statusPublished - 2006
Externally publishedYes


This work was supported in part by the Turkish Academy of Sciences (TUBA) and the State Planning Organization (2003K 120810).

FundersFunder number
Devlet Planlama Örgütü2003K 120810
Türkiye Bilimler Akademisi


    • Dielectric permittivity
    • Ferrocenyl
    • Phthalocyanine
    • Variable range hopping


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