Polymer phthalocyanines and their precursors 2. The structure of polyphthalocyanines

Bannehr, Rüdiger; Meyer, Georg; Wöhrle, Dieter

doi:10.1007/bf00255513

Cited by 36 publications

(17 citation statements)

References 5 publications

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“…Trimellitic acid was reacted with urea as an aminating source using the catalyst ammonium molybdate in the absence and presence of metal salts to give metal-free tetracarboxy phthalocyanine (MF-TcPc) and its metalized forms (Cu&Ni-TcPc), respectively. The phthalocyanine amide polymers were obtained by further reaction of either MF-TcPc, Cu or Ni-TcPc forms with 1,4-diaminobutane and 1,8-diaminonaph- DMSO S I I S I I NMF I I I I I I CHCl 3 I I I I I I Acetone I I I I I I Methanol I I I I I I Acetonitrile I I I I I I CH [8][9][10] and by Bannehr and co-workers 11 for the metal-free as well as the metalized phthalocyanines. It is worthy to notice that these bands are metal dependent and perturb slightly to higher wavenumbers in case of metalized phthalocyanines (compare spectrum a with b and c in Fig.…”

Section: Resultsmentioning

confidence: 99%

Phthalocyanine/laponite nanocomposites as multifunction additives for stabilization of polymeric materials

El‐Ghaffar

Elhalawany

Essawy

2008

J of Applied Polymer Sci

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Novel phthalocyanine amide polymers (Pc) based on 1,8-naphthalenediamine (Ar) as an aromatic amine and 1,4-diaminobutane (Al) as an aliphatic amine, were synthesized to improve the limited stabilization modes of conventional phthalocyanines. The metal-free phthalocyanines polymers (MF-Pc) were moderately soluble in DMSO only while the metalized forms (Cu&Ni-Pc) were completely insoluble. The structure of the samples was confirmed using Fourier transform infrared (FTIR), ultraviolet-visible spectrometry (UV-vis) and nuclear magnetic resonance (NMR). Additionally, the thermal stability and glass transition temperatures (T g ) were investigated by thermal gravimetric analyzer (TGA) and differential scanning calorimeter (DSC), respectively. The intercalation of the metal-free phthalocyanines, based on the aliphatic amine (MF-PcAl) and aromatic amine (MF-PcAr), into laponite from DMSO solution, was proved by X-ray diffraction (XRD). The basal space of laponite increased from 1.2 to 1.36 nm upon intercalation of MF-PcAl and extended more to 1.91 nm on using MF-PcAr as intercalant while the quaternized forms of MF-Pcs behaved likewise and could not widen the basal space of laponite to more than 1.43 nm which was attributed to the random distribution of the positive charges over the Pc chains which imposed confined arrangement inside the basal space and consequently narrower space than the attained one in the case of nonquaternized phthalocyanines. The plasticized PVC composites based on laponite treated with either MF-PcAl or MF-PcAr exhibited improved resistance to the UV radiation as revealed by the retention of the tensile strength and elongation at rupture after exposure to UV radiation for different time intervals.

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Section: Resultsmentioning

confidence: 99%

Phthalocyanine/laponite nanocomposites as multifunction additives for stabilization of polymeric materials

El‐Ghaffar

Elhalawany

Essawy

2008

J of Applied Polymer Sci

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“…[1,15a] One more important technique widely used in their works was the UV-Visible absorption. [1] More recently, reliable experimental data became available from XRD [20] and XPS techniques, [5] as well as TEM [32] and STM [26] imaging.…”

Section: Characterization Of 2d Ppcsmentioning

confidence: 99%

“…It was shown that concentrated sulfuric acid can dissolve some portion of the polymer due to protonation. [1] Nevertheless, the material of high polymerization degree was found to be insoluble even in this solvent [10a] showing thus the behavior similar to graphene. The alleged solubility of CoPPC in dimethyl sulfoxide (DMSO) and N-methylpyrrolidone (NMP) [4a] is a clear indication of low molecular weight.…”

Section: Other Characterization Techniquesmentioning

confidence: 99%

“…Despite its name, "polyphthalocyanine" (PPC) is in fact not a polymer of phthalocyanine. In the polymer, benzene rings are shared by the adjacent phthalocyanine units, therefore, unlike PC with four benzene rings per molecule, PPCs technically have only two benzene rings per unit cell [1] (Figure 1). The term "polyphthalocyanine" was introduced by Winslow and Antonelli in 1957 [2] and is conventionally used since then for these polymers, but it is important to understand that the "monomeric unit" of PPC is not the phthalocyanine.…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in 2D Polymeric Phthalocyanines: Synthesis, Characterization, Applications and New Challenges

Korepanov¹,

Sedlovets²

2019

MHC

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This article is dedicated to Prof. Dieter Wöhrle, whose works for a long time have been the highest standard and a source of inspiration for us 2D polyphthalocyanines (PPCs) are actively studied as advanced materials for new generation energy and microelectronics. Some time ago such compounds were dubbed "just a dream of synthetic chemists", what was a perfect reflection of, on the one hand, high promise, and, on the other hand, experimental difficulties faced with the 2D polymers. Despite a long history of PPCs (since late 1950s), it was shown recently that in many works the reaction products were misinterpreted , and the studied compounds should be assigned to a low degree of the polymerization. Recent years, the discovery of graphene has inspired a new wave of interest to PPCs. From the graphene point of view, the questions are: whether we can make other graphene-like materials with modified properties? Can we use metal atoms to tune its electronic properties? Can we make a magnetic 2D material? From the polymer chemistry point of view, the major problem is why the common synthetic approaches and characterization techniques didn't work for this polymer as expected? And how to identify the reaction products? This review covers evolution of the synthetic approaches, establishment of the reliable characterization techniques, as well as the promising applications of 2D PPCs and the "new dreams" in science and technology of these materials.

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“…For the polycyclotetramerization, bifunctional monomers based on tetracarbonitriles such as 1,2,4,5-tetracyanobenzene 2 for polymers 1 [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19], various oxy-, arylenedioxy-and alkylenedioxy-bridged diphthalonitriles 4 for polymers 3 [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] and other nitriles [35][36][37][38][39][40][41] or tetracarboxylic acid derivatives such as 1,2,4,5benzenetetracarboxylic acid dianhydride [35][36][37][38][39][40][41][42][43]…”

Section: Introductionmentioning

confidence: 99%

Syntheses of structurally uniform polymeric phthalocyanines

Wöhrle

Benters

Suvorova

et al. 2000

J. Porphyrins Phthalocyanines

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Very few papers describe the synthesis of structurally uniform polymeric phthalocyanines. Owing to their insolubility, it is difficult to get information on the structural uniformity, kind of end groups and molecular weight. The reaction conditions are severe to get well-defined polymeric phthalocyanines. In this paper, four methods are described to get pure polymeric phthalocyanines as powders by bulk or solution reactions and as thin films or coatings on carriers.

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Polymer phthalocyanines and their precursors 2. The structure of polyphthalocyanines

Cited by 36 publications

References 5 publications

Phthalocyanine/laponite nanocomposites as multifunction additives for stabilization of polymeric materials

Phthalocyanine/laponite nanocomposites as multifunction additives for stabilization of polymeric materials

Recent Advances in 2D Polymeric Phthalocyanines: Synthesis, Characterization, Applications and New Challenges

Syntheses of structurally uniform polymeric phthalocyanines

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