A phthalocyanine is a macrocycle having an alternating nitrogen atom-carbon atom ring structure. It is spelled "phthalozyanin" in German and "phtalocyanine" in French. The molecule is able to coordinate hydrogen and metal cations in its center by coordinate bonds with the four isoindole nitrogen atoms. The central atoms can carry additional ligands. Most of the elements have been found to be able to coordinate to the phthalocyanine macrocycle. Therefore, a variety of phthalocyanine complexes exist. ==History== The first known appearance of an unknown blue by-product (which we know by now was metal-free phthalocyanine) has been reported in 1907. In 1927, two researchers from Switzerland accidentally synthesized copper phthalocyanine, copper naphthalocyanine and copper octamethylphthalocyanine when they tried to convert o-dibromobenzene into phthalonitrile. They remarked the enormous stability of these complexes but failed to appreciate their discovery and to fully characterize these blue complexes. H. de Diesbach,E. von der Weid, Helevtica Chimica Acta, 1927, ''10'', 886. The ''real discovery'' also started as an accident, when a blue product was found in a reaction flask where only white product was expected. However, this accident occurred in a dye company, Scottish Dyes, Ltd., Grangemouth, Scotland (later Imperial Chemical Industries) and the discovery was followed on. ---- ==Overview== The structure of a phthalocyanine molecule is closely related to that of the naturally occurring porphyrin systems. The phthalocyanine macrocycle is also related to some other macrocyclic complexes, as e.g., the subphthalocyanine, superphthalocyanine or hemiporphyrazine. ==Synthesis== You can see in the figure below (left side) that a phthalocyanine macrocycle consists of four identical corners. A synthesis strategy, therefore, starts from molecules which correspond to these corners. Such molecules are derivatives of phthalic acid: e.g., phthalonitrile, o-cyanobenzamide, phthalanhydride, phthalimide or diiminoisoindole. Several of these starting materials are shown in the figure below (right side).
==Characterization== UV-Vis IR, Raman, NMR Powder diffraction ==Structures== Single-crystal structures *[http://phthalo.mkengel.de/pcrev.htm Phthalocyanine Crystal Structures] Liquid-crystalline structures ==Theoretical calculations and predictions== Crystal structure prediction Quantum-chemical calculations ==Properties== Electrical properties Optical and non-linear optical properties Magnetical properties ==Applications== Pigments Photoreceptors Dyes Catalysts Semiconductors ==External links== *[http://groups.yahoo.com/group/phthalo/ PHTHALO: The Phthalocyanine, Porphyrin, Dye and Pigment mailing list] *[http://www.u-bourgogne.fr/spp/ Society of Porphyrins and Phthalocyanines] *[http://www3.interscience.wiley.com/cgi-bin/jtoc/15661/ Journal of Porphyrins and Phthalocyanines, vol. 1 (1997) - vol. 5 (2001)] *[http://www.u-bourgogne.fr/jpp/base_article/index.php Journal of Porphyrins and Phthalocyanines, from vol. 6 (2002)] *[http://phthalo.mkengel.de/pcthesis.htm Journal of Phthalocyanine Theses] *[http://phthalo.mkengel.de/pcbooks.htm Phthalocyanine book list] *[http://phthalo.mkengel.de/researchers.htm Some Phthalocyanine researchers] ===Phthalocyanine books=== ''The Porphyrin Handbook'', Vols. 15-20; Karl Kadish, Kevin M. Smith, Roger Guilard (eds); Academic Press 2003 *[http://www.porphyrins.info/volumes/volume15.html Volume 15 – Phthalocyanines: Synthesis] *[http://www.porphyrins.info/volumes/volume16.html Volume 16 – Phthalocyanines: Spectroscopic and Electrochemical Characterization] *[http://www.porphyrins.info/volumes/volume17.html Volume 17 – Phthalocyanines: Properties and Materials] *[http://www.porphyrins.info/volumes/volume18.html Volume 18 – Multiporphyrins, Multiphthalocyanines and Arrays] **[http://www.porphyrins.info/pdf/KADISH-Vol_18-Chap_115.pdf Vol. 18, Chap. 115 - Self-Assembly of Chiral Phthalocyanines and Chiral Crown Ether Phthalocyanines] *[http://www.porphyrins.info/volumes/volume19.html Volume 19 – Applications of Phthalocyanines] *[http://www.porphyrins.info/volumes/volume20.html Volume 20 – Phthalocyanines: Structural Characterization] chemical compounds
==Scrap area== If you would like to have some information included in the article but don't have the time or energy to write it down, just put it in here. Over time, I will add it. mkengel The stability of a metal phthalocyanine coordination compound depends on the size of the intercalated metal cation. When a copper, nickel, zinc, cobalt, aluminum, platinum, or iron anion is inserted in the phthalocyanine ring, the resulting complex is quite stable. For example, unsubstituted copper-phthalocyanine is mainly used as blue pigment while substituted phthalocyanines are used as dye. However, the out of plane intercalation of sodium, potassium, calcium, barium, or mercury (element) cations which are to big to fit into the cavity of the phthalocyanine macrocycle is possible but the resulting coordination compounds are quite unstable and such metal phthalocyanines can be easily converted into metal-free phthalocyanine (H2Pc) which is also a valuable pigment whose color is a little bit more greenish than the copper phthalocyanine. Halogenated phthalocyanines are bright green pigments. The ring of phthalocyanine has π-electrons that can move via π-electron cloud overlaps; therefore high conductivity can occur. In fact, metal phthalocyanines are known to form conducting solids when the π-ligand is oxidized. Partially oxidized complex salts of [MPc]X (M = H2, Ni, Cu, etc.; Pc = phthalocyanine; X = I, (BF4)0.33, (SbF6)0.5,etc) are known to be metallic one-dimensional conductors. The crystals consist of one-dimensional face-to-face stacked phthalocyanine columns and one-dimensional anion chains.
See other meanings of words starting from letter:
Words begining with Phthalocyanine:
Phthalocyanine
Phthalocyanine
Phthalocyanine
A phthalocyanine is a macrocycle having an alternating nitrogen atom-carbon atom ring structure. It is spelled "phthalozyanin" in German and "phtalocyanine" in French. The molecule is able to coordinate hydrogen and metal cations in its center by coordinate bonds with the four isoindole nitrogen atoms. The central atoms can carry additional ligands. Most of the elements have been found to be able to coordinate to the phthalocyanine macrocycle. Therefore, a variety of phthalocyanine complexes exist. ==History== The first known appearance of an unknown blue by-product (which we know by now was metal-free phthalocyanine) has been reported in 1907. In 1927, two researchers from Switzerland accidentally synthesized copper phthalocyanine, copper naphthalocyanine and copper octamethylphthalocyanine when they tried to convert o-dibromobenzene into phthalonitrile. They remarked the enormous stability of these complexes but failed to appreciate their discovery and to fully characterize these blue complexes. H. de Diesbach,E. von der Weid, Helevtica Chimica Acta, 1927, ''10'', 886. The ''real discovery'' also started as an accident, when a blue product was found in a reaction flask where only white product was expected. However, this accident occurred in a dye company, Scottish Dyes, Ltd., Grangemouth, Scotland (later Imperial Chemical Industries) and the discovery was followed on. ---- ==Overview== The structure of a phthalocyanine molecule is closely related to that of the naturally occurring porphyrin systems. The phthalocyanine macrocycle is also related to some other macrocyclic complexes, as e.g., the subphthalocyanine, superphthalocyanine or hemiporphyrazine. ==Synthesis== You can see in the figure below (left side) that a phthalocyanine macrocycle consists of four identical corners. A synthesis strategy, therefore, starts from molecules which correspond to these corners. Such molecules are derivatives of phthalic acid: e.g., phthalonitrile, o-cyanobenzamide, phthalanhydride, phthalimide or diiminoisoindole. Several of these starting materials are shown in the figure below (right side).
==Characterization== UV-Vis IR, Raman, NMR Powder diffraction ==Structures== Single-crystal structures *[http://phthalo.mkengel.de/pcrev.htm Phthalocyanine Crystal Structures] Liquid-crystalline structures ==Theoretical calculations and predictions== Crystal structure prediction Quantum-chemical calculations ==Properties== Electrical properties Optical and non-linear optical properties Magnetical properties ==Applications== Pigments Photoreceptors Dyes Catalysts Semiconductors ==External links== *[http://groups.yahoo.com/group/phthalo/ PHTHALO: The Phthalocyanine, Porphyrin, Dye and Pigment mailing list] *[http://www.u-bourgogne.fr/spp/ Society of Porphyrins and Phthalocyanines] *[http://www3.interscience.wiley.com/cgi-bin/jtoc/15661/ Journal of Porphyrins and Phthalocyanines, vol. 1 (1997) - vol. 5 (2001)] *[http://www.u-bourgogne.fr/jpp/base_article/index.php Journal of Porphyrins and Phthalocyanines, from vol. 6 (2002)] *[http://phthalo.mkengel.de/pcthesis.htm Journal of Phthalocyanine Theses] *[http://phthalo.mkengel.de/pcbooks.htm Phthalocyanine book list] *[http://phthalo.mkengel.de/researchers.htm Some Phthalocyanine researchers] ===Phthalocyanine books=== ''The Porphyrin Handbook'', Vols. 15-20; Karl Kadish, Kevin M. Smith, Roger Guilard (eds); Academic Press 2003 *[http://www.porphyrins.info/volumes/volume15.html Volume 15 – Phthalocyanines: Synthesis] *[http://www.porphyrins.info/volumes/volume16.html Volume 16 – Phthalocyanines: Spectroscopic and Electrochemical Characterization] *[http://www.porphyrins.info/volumes/volume17.html Volume 17 – Phthalocyanines: Properties and Materials] *[http://www.porphyrins.info/volumes/volume18.html Volume 18 – Multiporphyrins, Multiphthalocyanines and Arrays] **[http://www.porphyrins.info/pdf/KADISH-Vol_18-Chap_115.pdf Vol. 18, Chap. 115 - Self-Assembly of Chiral Phthalocyanines and Chiral Crown Ether Phthalocyanines] *[http://www.porphyrins.info/volumes/volume19.html Volume 19 – Applications of Phthalocyanines] *[http://www.porphyrins.info/volumes/volume20.html Volume 20 – Phthalocyanines: Structural Characterization] chemical compounds
Phthalocyanine
==Scrap area== If you would like to have some information included in the article but don't have the time or energy to write it down, just put it in here. Over time, I will add it. mkengel The stability of a metal phthalocyanine coordination compound depends on the size of the intercalated metal cation. When a copper, nickel, zinc, cobalt, aluminum, platinum, or iron anion is inserted in the phthalocyanine ring, the resulting complex is quite stable. For example, unsubstituted copper-phthalocyanine is mainly used as blue pigment while substituted phthalocyanines are used as dye. However, the out of plane intercalation of sodium, potassium, calcium, barium, or mercury (element) cations which are to big to fit into the cavity of the phthalocyanine macrocycle is possible but the resulting coordination compounds are quite unstable and such metal phthalocyanines can be easily converted into metal-free phthalocyanine (H2Pc) which is also a valuable pigment whose color is a little bit more greenish than the copper phthalocyanine. Halogenated phthalocyanines are bright green pigments. The ring of phthalocyanine has π-electrons that can move via π-electron cloud overlaps; therefore high conductivity can occur. In fact, metal phthalocyanines are known to form conducting solids when the π-ligand is oxidized. Partially oxidized complex salts of [MPc]X (M = H2, Ni, Cu, etc.; Pc = phthalocyanine; X = I, (BF4)0.33, (SbF6)0.5,etc) are known to be metallic one-dimensional conductors. The crystals consist of one-dimensional face-to-face stacked phthalocyanine columns and one-dimensional anion chains.
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P
PA | PB | PC | PD | PE | PF | PG | PH | PI | PJ | PK | PL | PM | PN | PO | PR | PS | PT | PU | PW | PX | PY | PZ |Words begining with Phthalocyanine:
Phthalocyanine
Phthalocyanine
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