Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyaninates

Cuellar, Edward A.; Marks, Tobin J.

doi:10.1021/ic50225a039

Cited by 117 publications

(47 citation statements)

References 2 publications

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“…For instance, when this ratio is 1 : 7.8, the yield of tetrakis(trimethylsilyl)phthalocyanine is 13%, which can be increased if a 1 : 32 ratio is used. 62,90 It is interesting to note that despite the bulkiness of the trimethylsilyl groups, all four possible isomers of H 2 Pc(SiMe 3 ) 4 were observed in the 29 Si NMR spectrum. Similarly, lithiation of the zinc phthalocyanine followed by treatment with Me 3 SiCl leads to formation of polysilylated zinc phthalocyanine.…”

Section: Scheme 21mentioning

confidence: 99%

“…Upon its cyclotetramerization, metal-free 1,8(11),15(18),22(25)-tetrakis(trimethylsilyl)phthalocyanine was prepared. 90 The target phthalocyanine is readily soluble in chlorinated hydrocarbons and gives a single 29 Si NMR peak at δ = -2.366 ppm relative to TMS. Chen et al suggested that the direct lithiation of the phthalocyanine core predominantly, if not exclusively, occurs at the α-peripheral positions of the phthalocyanine ring, and this can be used to selectively introduce α-peripheral substituents onto the phthalocyanine core.…”

Section: Scheme 21mentioning

confidence: 99%

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Synthesis of substituted phthalocyanines

Nemykin¹,

Luk’yanets²

2010

Arkivoc

151

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This review summarizes the synthetic strategies for substituted phthalonitriles and phthalocyanines. Preparation of alkyl-, aryl-, halo-, nitro-, alkoxy-, aryloxy-, alkylthio-, arylthio-, and amino-substituted phthalocyanines along with the derivatives of phthalocyanine carboxylicand sulfoacids is overviewed. Influence of the substituents on the position of Q-band in UV-vis spectra of substituted phthalocyanines is also briefly discussed.

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Section: Scheme 21mentioning

confidence: 99%

Section: Scheme 21mentioning

confidence: 99%

Synthesis of substituted phthalocyanines

Nemykin¹,

Luk’yanets²

2010

Arkivoc

151

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“…The spectrum of N-tosylated copper phthalocyaninate 4b in DMF is typical for phthalocyanines with bulky substituents such as crown ethers, aminophenoxy or aminophenylsulfanyl and long alkoxy chains [6,7,27,28]. Increasing the polarity of the solvent has been shown to generally result in the aggregation of phthalocyanines which is easily monitored by the position of the Q band, which is shifted to shorter wavelengths, and a decrease in the molar absorption coefficient [6,7,29]. The obvious effect of alkali metal ions complexed in the crown ether groups on the Q band transitions of the phthalocyanine unit should be appreciated [9].…”

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confidence: 99%

Synthesis and Properties of Copper(II) Phthalocyanines with Monoazacrown and Crown Ethers as Peripheral Substituents

Kandaz

Bekâroĝlu

1999

J. Porphyrins Phthalocyanines

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Soluble and less soluble phthalocyaninatocopper(II) derivatives (4a and 4b) were prepared from the corresponding 7-[(4′-benzo-15-crown-5)oyl]-15, 16-dibromo-2,3,6,7,8,9,11,12-octahydro-5H-benzo[e]-[1,4,10,13,7] tetraoxaazacyclopentadecine (3a) and 7-(2′-tosylaminoethyl)-15, 16-dibromo-2,3,6,7,8,9,11, 12-octahydro-5H-benzo[e]-[1,4,10,13,7] tetraoxaazacyclopentadecine (3b) and CuCN in pyridine. A less soluble novel multifunctionalized scorpiand macrocycle-substituted phthalocyanine (4c) in which an NH 2 CH 2 CH 2— chain is appended to a monoazacrown ether ring was obtained by detosylation of 4b with concentrated sulfuric acid.

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“…All the phthalocyanines (4-8) exhibited both endothermic and exothermic DSC thermograms in the studied temperature range. 45 Broad endothermic peaks in DSC thermograms between 50 and 100 • C are ascribed to the alcohol and water desorption during the synthesis or the adsorbed humidity or air gases' desorption during storage of the samples. Table 2).…”

Section: Dsc and Dtg/tga Measurementsmentioning

confidence: 99%

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

Bílgín

Yanmaz²,

Yağcı³

2014

Turk J Chem

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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.

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Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyaninates

Cited by 117 publications

References 2 publications

Synthesis of substituted phthalocyanines

Synthesis of substituted phthalocyanines

Synthesis and Properties of Copper(II) Phthalocyanines with Monoazacrown and Crown Ethers as Peripheral Substituents

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

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