Stability of benzotriazolyl-substituted phthalocyanines with respect to thermal oxidative decomposition

Synthesis and Properties of Sulfo and Alkylsulfamoyl Substituted Phthalocyanines and their Copper (II) Complexes Bearing 1-Benzotriazolyl and 4-Cyclohexylphenoxy Groups

“…The first one occurs in the temperature range 280-360 °C. According to the weight loss value observed on TG curves (27.91 % for 4a and 23.35 % for 1a), the decomposition occurs with the participation of benzotriazolyl substituents, as it was found previously for other phthalocyanines combining on the periphery benzotriazolyl and oxyaryl groups [14]. For example for compounds 4a and 1a, heated up to 290 °C, in the IR spectra there was no band corresponding to the stretching vibrations of N=N bond of benzotriazolyl fragment (1040-1050 cm -1 ).…”

Layer-by-layer assembled highly absorbing hundred-layer films containing a phthalocyanine dye: Fabrication and photosensibilization by thermal treatment

“…The shifts of several cm -1 and the different intensities were not sufficient to identify the CuPcTs crystalline structure by Raman spectroscopy [72]. However, the preservation of the characteristic peaks of CuPcTs in Raman spectra could be evidence of the thermal stability of the used phthalocyanine (resistance of a molecule to decomposition) in the examined temperature range [79,80].…”

Modified Method for Synthesis of 4-(Aryloxy)-5-(1-benzotryazolyl) Phthalonitriles

“…[15,16] Influence of reaction conditions, particularly reaction temperature on the yield of substitution of nitro group by benzotriazolyl fragment was studied in the case of preparation of 4-(1-benzotriazolyl)-5-(2-naphthoxy)phthalonitrile (10). It was found that the best results were achieved at 65-70 ºC.…”

“…[1,3,5,6] For example metal complexes of 1,8,15,22-tetrakis(phenylsulfanyl)-3,10, 17,24-tetrakis(tert-butyl)phthalocyanine with manganese chloride, zinc and aluminum hydroxide proposed as contrasting agent for magnetic-resonance diagnostic of tumors [7] and immunoliposomal form of photosensitiser. [8] Combination of benzotriazolyl and aryloxy fragments on the periphery of phthalocyanine molecule provides high solubility in organic solvents, [9] thermo stability on air under high temperatures, [10] liquid crystalline properties. [11,12] Furthermore these phthalocyanine derivatives readily form sulfo-derivatives [13] and sulfochlorides [14] at room temperature.…”

“…Synthesis of 2,9,16,23-tetrakis(1-benzotriazolyl)-3,10,17,24-tetrakis-(aryloxy) phthalocyanines and their metal complexes was developed on the basis of corresponding disubstituted phthalonitriles. [10][11][12][13][14] Three-stage process for preparation of these phthalonitriles with total duration of 5.5 hours was elaborated previously. [15,16] The purpose of the study was a finding of simplified method for the synthesis of these compounds from 4-bromo-5-nitrophthalonitrile which would reduce number of synthetic operations preserving synthetic yield.…”