Synthesis and properties of novel polymeric metal-free and metallophthalocyanines containing peripherally long 1,2-bis[(3-oxapropyl)oxa]benzene derivatives

Abstract

New polymeric phthalocyanine moieties (M = 2H, Zn, Ni, Cu, and Co) were synthesized via polytetracyclomerization reaction of o -bis[3-(3,4-dicyanophenoxy)propyloxy]benzene (3), which can be obtained by the reaction of 4-nitrophthalonitrile with o -bis[(3-hydroxypropyl)oxy]benzene. Aggregation and disaggregation behavior of the polymeric phthalocyanine ( 5) was studied with some alkali and earth alkali metal cations. Measured intrinsic viscosities of the polymeric phthalocyanines exhibited a substantial decreasing tendency with dilution of the solution. Thermogravimetric analysis was performed under air by using DSC and DTG/TGA techniques and indicated that these polymers have good thermal stability. AC and DC electrical conductivities of the polymeric phthalocyanines were investigated in the frequency range 100 Hz-1 MHz within the temperature range 298-343 K. AC/DC conductivities of the samples were found to be between 10 −5 and 10 −7 S cm −1 at ambient temperature under argon atmosphere. The structures of new synthesized compounds were characterized by using microanalysis; various spectroscopic methods such as UV-Vis, FT-IR, 1 H NMR, and 13 C NMR spectroscopy; and MS spectra.

Synthetic Methodologies for Chelating Polymer Ligands: Recent Advances and Future Development

“…Phthalocyanine polymers were obtained by the polytetracyclomerization of o‐bis[3‐(3,4‐dicyanophenoxy)propyloxy]benzene synthesized by reacting 4‐nitrophtalonitrile with o ‐bis[(3‐hydroxypropyl)oxy]benzene …”

Synthesis and Characterization of Phthalocyaninatosilicon With Bridging Ligands (L) (L = Dimethylsilane, Diphenylsilane, Methylphenylsilane)

“…1,2 Metallomacrocycles such as metallophthalocyanines (PcMs) and metallonaphthalocyanines (NcMs), besides their many other possible applications such as dyes, catalysts, pigments, etc., have recently been intensively investigated in the area of their electrical conductivity, as part of the efforts to construct new types of bridging ligand metallomacrocyclic compounds. [3][4][5] Many conducting and semiconducting organic compounds have been developed during the last two decades. They include charge-transfer complexes, doped polyacetylene, polypyrrole, polythiophene, polyaniline, and others.…”