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

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

See 1 more Smart Citation

Synthesis of substituted phthalocyanines

Nemykin¹,

Luk’yanets²

2010

Arkivoc

155

View full text Add to dashboard Cite

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.

show abstract

Section: Scheme 21mentioning

confidence: 99%

Section: Scheme 21mentioning

confidence: 99%

Synthesis of substituted phthalocyanines

Nemykin¹,

Luk’yanets²

2010

Arkivoc

155

View full text Add to dashboard Cite

show abstract

“…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].…”

mentioning

confidence: 99%

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

Kandaz

Bekâroĝlu

1999

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

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.

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

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

Contact Info

Product

Resources

About