User:FacetiousLobster/sandbox

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FacetiousLobster/sandbox
Skeletal formula
Ball-and-stick model
Names
Other names
  • Phthalocyanin
  • Pigment Blue 16
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C32H18N8/c1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25/h1-16H,(H2,33,34,35,36,37,38,39,40) ☒N
    Key: IEQIEDJGQAUEQZ-UHFFFAOYSA-N ☒N
  • InChI=1S/C32H18N8/c1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25/h1-16H,(H2,33,34,35,36,37,38,39,40)
    Key: IEQIEDJGQAUEQZ-UHFFFAOYSA-N
  • C12=CC=CC=C1/C3=N/C4=C5C=CC=CC5=C(/N=C6C7=CC=CC=C7C(/N=C8C9=C(/C(N/8)=N/C2=N3)C=CC=C9)=N/6)N4
Properties
C32H18N8
Molar mass 514.552 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tracking categories (test):

Phthalocyanine (H2Pc) is a large,

catalysis, organic solar cells, and photodynamic therapy
.

Properties

Phthalocyanine and derived metal complexes (MPc) tend to aggregate and, thus, have low solubility in common solvents.

near infrared
).

There are many derivatives of the parent phthalocyanine, where either carbon atoms of the macrocycle are exchanged for nitrogen atoms or the peripheral hydrogen atoms are substituted by functional groups like

nitrosyl groups. These modifications allow for the tuning of the electrochemical properties of the molecule such as absorption and emission wavelengths and conductance.[5]

History

In 1907, an unidentified blue compound, now known to be phthalocyanine, was reported.[6] In 1927, Swiss researchers serendipitously discovered copper phthalocyanine, copper naphthalocyanine, and copper octamethylphthalocyanine in an attempted conversion of o-dibromobenzene into phthalonitrile. They remarked on the enormous stability of these complexes but did not further characterize them.[7] In the same year, iron phthalocyanine was discovered at Scottish Dyes of Grangemouth, Scotland (later ICI).[8] It was not until 1934 that Sir Patrick Linstead characterized the chemical and structural properties of iron phthalocyanine.[9]

Synthesis

Phthalocyanine is formed through the cyclotetramerization of various

phthalanhydride in the presence of urea yields H2Pc.[11] Using such methods, approximately 57,000 tonnes (63,000 tons) of various phthalocyanines were produced in 1985.[11]

HOMO/LUMO bands rather than atomic profiles.[12]

More often, MPc is synthesized rather H2Pc due to the greater research interest in the former. To prepare these complexes, the phthalocyanine synthesis is conducted in the presence of metal salts. Two copper phthalocyanines are shown in the figure below.

CuPc with chlorine, bromine or oleum
.

Applications

See also: Copper phthalocyanine

At the initial discovery of Pc, its uses were primarily limited to dyes and pigments.

biosensing.[19][20][21]

Toxicity and hazards

No evidence has been reported for acute toxicity or carcinogenicity of phthalocyanine compounds. The LD50 (rats, oral) is 10 g/kg.[11]

Related compounds

Relationship of the phthalocyanine with the porphyrin macrocycle. Two intramacrocyclic N-H groups are omitted.

Phthalocyanines are structurally related to other

conjugate base
of H
2Pc.

References

  1. ^ Pubchem. "Pigment blue 16". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-04-08.
  2. ^
    ISSN 0021-9568
    .
  3. ISSN 0022-2461
    .
  4. doi:10.3998/ark.5550190.0011.104
    .
  5. ISSN 2040-3372
    .
  6. doi:10.1002/cber.190704002202
    .
  7. doi:10.1002/hlca.192701001110
    .
  8. ^ "The Discovery of a New Pigment—The Story of Monastral Blue by Imperial Chemical Industries". colorantshistory.org.
  9. ISSN 0368-1769
    .
  10. doi:10.3390/ma2031127.{{cite journal}}: CS1 maint: unflagged free DOI (link
    )
  11. ^
    ISBN 978-3527306732
    ..
  12. PMID 24828002
    .
  13. ISSN 0019-7866
    .
  14. ISSN 1528-0691
    .
  15. ISSN 2046-2069
    .
  16. doi:10.1016/j.solener.2012.03.019
    .
  17. ISSN 0009-2665
    .
  18. doi:10.1016/j.taap.2007.01.025
    .
  19. doi:10.1016/j.cplett.2006.12.007
    .
  20. ISSN 0743-7463
    .
  21. doi:10.1016/j.bioelechem.2009.02.005
    .

External links

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