Phthalocyanine

Last updated
Phthalocyanine
Phthalocyanine.svg
Phthalocyanine-3D-balls.png
Names
Other names
  • Phthalocyanin
  • Pigment Blue 16
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.527 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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) X mark.svgN
    Key: IEQIEDJGQAUEQZ-UHFFFAOYSA-N X mark.svgN
  • InChI=1/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-UHFFFAOYAC
  • C1=CC=C2C(=C1)C3=NC4=C5C=CC=CC5=C(N4)N=C6C7=CC=CC=C7C(=N6)N=C8C9=CC=CC=C9C(=N8)N=C2N3
Properties
C32H18N8
Molar mass 514.552 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Phthalocyanine (H2Pc) is a large, aromatic, macrocyclic, organic compound with the formula (C8H4N2)4H2 and is of theoretical or specialized interest in chemical dyes and photoelectricity.

Contents

It is composed of four isoindole units [a] linked by a ring of nitrogen atoms. (C8H4N2)4H2 = H2Pc has a two-dimensional geometry and a ring system consisting of 18  π-electrons. The extensive delocalization of the π-electrons affords the molecule useful properties, lending itself to applications in dyes and pigments. Metal complexes derived from Pc2−
, the conjugate base of H2Pc, are valuable in catalysis, organic solar cells, and photodynamic therapy.

Properties

STM images of individual phthalocyanine molecules recorded at a bias of -2 V (left) and +1 V (right). Note that STM probes density of electrons in the HOMO/LUMO bands rather than atomic profiles. Phthalocyanine STM.jpg
STM images of individual phthalocyanine molecules recorded at a bias of −2 V (left) and +1 V (right). Note that STM probes density of electrons in the HOMO/LUMO bands rather than atomic profiles.

Phthalocyanine and derived metal complexes (MPc) tend to aggregate and, thus, have low solubility in common solvents. [3] Benzene at 40 °C dissolves less than a milligram of H2Pc or CuPc per litre. H2Pc and CuPc dissolve easily in sulfuric acid due to the protonation of the nitrogen atoms bridging the pyrrole rings. Many phthalocyanine compounds are, thermally, very stable and do not melt but can be sublimed. CuPc sublimes at above 500 °C under inert gases (nitrogen, CO2). [4] Substituted phthalocyanine complexes often have much higher solubility. [5] They are less thermally stable and often can not be sublimed. Unsubstituted phthalocyanines strongly absorb light between 600 and 700  nm, thus these materials are blue or green. [3] Substitution can shift the absorption towards longer wavelengths, changing color from pure blue to green to colorless (when the absorption is in the 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 halogens, hydroxyl, amine, alkyl, aryl, thiol, alkoxy and nitrosyl groups. These modifications allow for the tuning of the electrochemical properties of the molecule such as absorption and emission wavelengths and conductance. [6]


History

In 1907, an unidentified blue compound, now known to be phthalocyanine, was reported. [7] 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. [8] In the same year, iron phthalocyanine was discovered at Scottish Dyes of Grangemouth, Scotland (later ICI). [9] It was not until 1934 that Sir Patrick Linstead characterized the chemical and structural properties of iron phthalocyanine. [10]

Synthesis

Phthalocyanine is formed through the cyclotetramerization of various phthalic acid derivatives including phthalonitrile, diiminoisoindole, phthalic anhydride, and phthalimides. [11] Alternatively, heating phthalic anhydride in the presence of urea yields H2Pc. [12] Using such methods, approximately 57,000 tonnes (63,000 Imperial tons) of various phthalocyanines were produced in 1985. [12] More often, MPc is synthesized rather than 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.

Copper phthalocyanine.svg Phthalocyanine Green G.png

Halogenated and sulfonated derivatives of copper phthalocyanines are commercially important as dyes. Such compounds are prepared by treating CuPc with chlorine, bromine or oleum.

Applications

Sample of copper phthalocyanine, illustrating the intense color characteristic of phthalocyanine derivatives. Copper Phtalocyanine Blue.JPG
Sample of copper phthalocyanine, illustrating the intense color characteristic of phthalocyanine derivatives.

At the initial discovery of Pc, its uses were primarily limited to dyes and pigments. [13] Modification of the substituents attached to the peripheral rings allows for the tuning of the absorption and emission properties of Pc to yield differently colored dyes and pigments. There has since been significant research on H2Pc and MPc resulting in a wide range of applications in areas including photovoltaics, photodynamic therapy, nanoparticle construction, and catalysis. [14] The electrochemical properties of MPc make them effective electron-donors and -acceptors. As a result, MPc-based organic solar cells with power conversion efficiencies at or below 5% have been developed. [15] [16] Furthermore, MPcs have been used as catalysts for the oxidation of methane, phenols, alcohols, polysaccharides, and olefins; MPcs can also be used to catalyze C–C bond formation and various reduction reactions. [17] Silicon and zinc phthalocyanines have been developed as photosensitizers for non-invasive cancer treatment. [18]

Various MPcs have also shown the ability to form nanostructures which have potential applications in electronics and biosensing. [19] [20] [21] Phthalocyanine is also used on some recordable DVDs. [22]

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

Phthalocyanines are structurally related to other tetrapyrrole macrocyles including porphyrins and porphyrazines. They feature four pyrrole-like subunits linked to form a 16 membered inner ring composed of alternating carbon and nitrogen atoms. Structurally larger analogues include naphthalocyanines. The pyrrole-like rings within H2Pc are closely related to isoindole. Both porphyrins and phthalocyanines function as planar tetradentate dianionic ligands that bind metals through four inwardly projecting nitrogen centers. Such complexes are formally derivatives of Pc2−, the conjugate base of H2Pc.

Soluble phthalocyanines

Of fundamental but little practical value, soluble phthalocyanines have been prepared. Long alkyl chains can be added to improve their solubility in organic solvents. [23] Soluble derivatives can be used for spin-coating or drop-casting. Alternatively, introducing ionic or hydrophilic groups into the structure can confer water solubility. [24] [25]

Solubilization can also be achieved through axial coordination. [26] [27] For instance, the axial ligand functionalization of silicon phthalocyanine has been extensively studied.

Toxicity and hazards

No evidence has been reported for acute toxicity or carcinogenicity of phthalocyanine compounds. The LD50 (rats, oral) is 10 g/kg. [12]

Footnotes

  1. ↑ One "isoindole unit" is C8H4N2; four in a nitrogen-ring configuration are abbreviated as symbol Pc = (C8H4N2)4 .

Related Research Articles

Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula C4H4NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.

<span class="mw-page-title-main">Porphyrin</span> Heterocyclic organic compound with four modified pyrrole subunits

Porphyrins are a group of heterocyclic, macrocyclic, organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges. In vertebrates, an essential member of the porphyrin group is heme, which is a component of hemoproteins, whose functions include carrying oxygen in the bloodstream. In plants, an essential porphyrin derivative is chlorophyll, which is involved in light harvesting and electron transfer in photosynthesis.

<span class="mw-page-title-main">Chlorin</span> Chemical compound

In organic chemistry, chlorins are tetrapyrrole pigments that are partially hydrogenated porphyrins. The parent chlorin is an unstable compound which undergoes air oxidation to porphine. The name chlorin derives from chlorophyll. Chlorophylls are magnesium-containing chlorins and occur as photosynthetic pigments in chloroplasts. The term "chlorin" strictly speaking refers to only compounds with the same ring oxidation state as chlorophyll.

<span class="mw-page-title-main">Conjugated system</span> System of connected p-orbitals with delocalized electrons in a molecule

In theoretical chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases stability. It is conventionally represented as having alternating single and multiple bonds. Lone pairs, radicals or carbenium ions may be part of the system, which may be cyclic, acyclic, linear or mixed. The term "conjugated" was coined in 1899 by the German chemist Johannes Thiele.

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Photodynamic therapy (PDT) is a form of phototherapy involving light and a photosensitizing chemical substance used in conjunction with molecular oxygen to elicit cell death (phototoxicity).

<span class="mw-page-title-main">Copper phthalocyanine</span> Synthetic blue pigment from the group of phthalocyanine dyes

Copper phthalocyanine (CuPc), also called phthalocyanine blue, phthalo blue and many other names, is a bright, crystalline, synthetic blue pigment from the group of dyes based on phthalocyanines. Its brilliant blue is frequently used in paints and dyes. It is highly valued for its superior properties such as light fastness, tinting strength, covering power and resistance to the effects of alkalis and acids. It has the appearance of a blue powder, insoluble in most solvents including water.

<span class="mw-page-title-main">Corrole</span> Aromatic tetrapyrrole

A corrole is an aromatic tetrapyrrole. The corrin ring is also present in cobalamin (vitamin B12). The ring consists of nineteen carbon atoms, with four nitrogen atoms in the core of the molecule. In this sense, corrole is very similar to porphyrin.

<span class="mw-page-title-main">Isoindole</span> Chemical compound

In organic chemistry and heterocyclic chemistry, isoindole consists of a benzene ring fused with pyrrole. The compound is an isomer of indole. Its reduced form is isoindoline. The parent isoindole is a rarely encountered in the technical literature, but substituted derivatives are useful commercially and occur naturally. Isoindoles units occur in phthalocyanines, an important family of dyes. Some alkaloids containing isoindole have been isolated and characterized.

<span class="mw-page-title-main">BODIPY</span> Parent chemical compound of the BODYPY fluorescent dyes

BODIPY is the technical common name of a chemical compound with formula C
9H
7BN
2F
2, whose molecule consists of a boron difluoride group BF
2 joined to a dipyrromethene group C
9H
7N
2; specifically, the compound 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene in the IUPAC nomenclature. The common name is an abbreviation for "boron-dipyrromethene". It is a red crystalline solid, stable at ambient temperature, soluble in methanol.

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<span class="mw-page-title-main">Phthalonitrile</span> Chemical compound

Phthalonitrile is an organic compound with the formula C6H4(CN)2, which is an off-white crystal solid at room temperature. It is a derivative of benzene, containing two adjacent nitrile groups. The compound has low solubility in water but is soluble in common organic solvents. The compound is used as a precursor to phthalocyanine and other pigments, fluorescent brighteners, and photographic sensitizers.

<span class="mw-page-title-main">Porphyrazine</span> Chemical compound

Porphyrazines, or tetraazaporphyrins, are tetrapyrrole macrocycles similar to porphyrins and phthalocyanines. Pioneered by Sir R. Patrick Linstead as an extension of his work on phthalocyanines, porphyrazines differ from porphyrins in that they contain -meso nitrogen atoms, rather than carbon atoms, and differ from phthalocyanines in that their β-pyrrole positions are open for substitution. These differences confer physical properties that are distinct from both porphyrins and phthalocyanines.

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<span class="mw-page-title-main">Transition metal porphyrin complexes</span>

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<span class="mw-page-title-main">Phosphorus porphyrin</span> Organophosphorus compound

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References

  1. ↑ "Pigment blue 16". pubchem.ncbi.nlm.nih.gov. Pubchem. U.S. National Institute of Health. Archived from the original on 2017-11-07. Retrieved 2018-04-08.
  2. ↑ Iannuzzi, Marcella; Tran, Fabien; Widmer, Roland; Dienel, Thomas; Radican, Kevin; Ding, Yun; Hutter, Jürg; Gröning, Oliver (2014). "Site-selective adsorption of phthalocyanine on h-BN/Rh(111) nanomesh". Physical Chemistry Chemical Physics. 16 (24): 12374–12384. Bibcode:2014PCCP...1612374I. doi: 10.1039/C4CP01466A . PMID   24828002.
  3. 1 2 Ghani, Fatemeh; Kristen, Juliane; Riegler, Hans (2012-02-09). "Solubility properties of unsubstituted metal phthalocyanines in different types of solvents". Journal of Chemical & Engineering Data. 57 (2): 439–449. doi:10.1021/je2010215. ISSN   0021-9568.
  4. ↑ Wagner, Hans J.; Loutfy, Rafik O.; Hsiao, Cheng-Kuo (1982-10-01). "Purification and characterization of phthalocyanines". Journal of Materials Science. 17 (10): 2781–2791. Bibcode:1982JMatS..17.2781W. doi:10.1007/bf00644652. ISSN   0022-2461. S2CID   96336392.
  5. ↑ Nemykin, Victor N.; Lukyanets, Evgeny A. (2010-02-18). "Synthesis of substituted phthalocyanines". Arkivoc. 2010 (1): 136. doi: 10.3998/ark.5550190.0011.104 . hdl: 2027/spo.5550190.0011.104 .
  6. ↑ Siles, P.F.; Hahn, T.; Salvan, G.; Knupfer, M.; Zhu, F.; Zahn, D.R.T.; Schmidt, O.G. (2016-04-21). "Tunable charge transfer properties in metal-phthalocyanine heterojunctions". Nanoscale. 8 (16): 8607–8617. Bibcode:2016Nanos...8.8607S. doi: 10.1039/c5nr08671j . ISSN   2040-3372. PMID   27049842.
  7. ↑ Braun, A.; Tcherniac, J. (1907). "Über die Produkte der Einwirkung von Acetanhydrid auf Phthalamid" [On the products of the reaction of acetic anhydride with phthalamide]. Berichte der Deutschen Chemischen Gesellschaft (in German). 40 (2): 2709–2714. doi:10.1002/cber.190704002202. Archived from the original on 2017-09-16. Retrieved 2015-09-15.
  8. ↑ de Diesbach, Henri; von der Weid, Edmond (1927). "Quelques sels complexes des o-dinitriles avec le cuivre et la pyridine" [Certain complex salts of o-dinitriles with copper and pyridine]. Helvetica Chimica Acta (in French). 10: 886–888. doi:10.1002/hlca.192701001110.
  9. ↑ "The discovery of a new pigment: The story of Monastral blue by Imperial Chemical Industries". colorantshistory.org. Archived from the original on 2009-07-25. Retrieved 2010-01-18.{{cite web}}: CS1 maint: unfit URL (link)
  10. ↑ Linstead, R.P. (1934-01-01). "212. Phthalocyanines. Part I. A new type of synthetic colouring matters". Journal of the Chemical Society. (resumed): 1016. doi:10.1039/jr9340001016. ISSN   0368-1769.
  11. ↑ Sakamoto, Keiichi; Ohno-Okumura, Eiko (2009-08-28). "Syntheses and functional properties of phthalocyanines". Materials. 2 (3): 1127–1179. Bibcode:2009Mate....2.1127S. doi: 10.3390/ma2031127 . PMC   5445737 .
  12. 1 2 3 Löbbert, Gerd. "Phthalocyanines". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_213. ISBN   978-3527306732.
  13. ↑ Dahlen, Miles A. (1939-07-01). "The phthalocyanines: A new class of synthetic pigments and dyes". Industrial & Engineering Chemistry. 31 (7): 839–847. doi:10.1021/ie50355a012. ISSN   0019-7866.
  14. ↑ Claessens, Christian G.; Hahn, Uwe; Torres, Tomás (2008). "Phthalocyanines: From outstanding electronic properties to emerging applications". The Chemical Record. 8 (2): 75–97. doi:10.1002/tcr.20139. ISSN   1528-0691. PMID   18366105.
  15. ↑ Kumar, Challuri Vijay; Sfyri, Georgia; Raptis, Dimitrios; Stathatos, Elias; Lianos, Panagiotis (2014-12-10). "Perovskite solar cell with low cost Cu-phthalocyanine as hole transporting material". RSC Advances. 5 (5): 3786–3791. doi:10.1039/c4ra14321c. ISSN   2046-2069. S2CID   84832945.
  16. ↑ Yuen, Avery P.; Jovanovic, Stephen M.; Hor, Ah-Mee; Klenkler, Richard A.; Devenyi, Gabriel A.; Loutfy, Rafik O.; Preston, John S. (2012). "Photovoltaic properties of M-phthalocyanine/fullerene organic solar cells". Solar Energy. 86 (6): 1683–1688. Bibcode:2012SoEn...86.1683Y. doi:10.1016/j.solener.2012.03.019. S2CID   55531280.
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  18. ↑ Miller, J.; Baron, E.; Scull, H.; Hsia, A.; Berlin, J.; Mccormick, T.; Colussi, V.; Kenney, M.; Cooper, K. (2007). "Photodynamic therapy with the phthalocyanine photosensitizer Pc 4: The case experience with preclinical mechanistic and early clinical–translational studies". Toxicology and Applied Pharmacology. 224 (3): 290–299. doi:10.1016/j.taap.2007.01.025. PMC   2128784 . PMID   17397888.
  19. ↑ Karan, Santanu; Basak, Dhrubajyoti; Mallik, Biswanath (2007). "Copper phthalocyanine nanoparticles and nanoflowers". Chemical Physics Letters. 434 (4–6): 265–270. Bibcode:2007CPL...434..265K. doi:10.1016/j.cplett.2006.12.007.
  20. ↑ van Keuren, Edward; Bone, Alysia; Ma, Changbao (2008-06-01). "Phthalocyanine nanoparticle formation in supersaturated solutions". Langmuir. 24 (12): 6079–6084. doi:10.1021/la800290s. ISSN   0743-7463. PMID   18479155.
  21. ↑ Lokesh, K.S.; Shivaraj, Y.; Dayananda, B.P.; Chandra, Sudeshna (2009). "Synthesis of phthalocyanine stabilized rhodium nanoparticles and their application in biosensing of cytochrome c". Bioelectrochemistry. 75 (2): 104–109. doi:10.1016/j.bioelechem.2009.02.005. PMID   19303822.
  22. ↑ "Mitsui Gold Archival DVD-R and DVD+R". www.conservationresources.com. Archived from the original on 2018-11-26. Retrieved 2020-04-13.
  23. ↑ Cook, Michael J. (July 2002). "Properties of Some Alkyl Substituted Phthalocyanines and Related Macrocycles". The Chemical Record. 2 (4): 225–236. doi:10.1002/tcr.10028. ISSN   1527-8999.
  24. ↑ Li, Hairong; Jensen, Timothy J.; Fronczek, Frank R.; Vicente, M. Graça H. (2008-02-01). "Syntheses and Properties of a Series of Cationic Water-Soluble Phthalocyanines". Journal of Medicinal Chemistry. 51 (3): 502–511. doi:10.1021/jm070781f. ISSN   0022-2623.
  25. ↑ Teles Ferreira, Joana; Pina, João; Alberto Fontes Ribeiro, Carlos; Fernandes, Rosa; Tomé, João P. C.; Rodríguez-Morgade, M. Salomé; Torres, Tomás (2017). "PEG-containing ruthenium phthalocyanines as photosensitizers for photodynamic therapy: synthesis, characterization and in vitro evaluation". Journal of Materials Chemistry B. 5 (29): 5862–5869. doi:10.1039/C7TB00958E. ISSN   2050-750X.
  26. ↑ Chen, Kejun; Liu, Kang; An, Pengda; Li, Huangjingwei; Lin, Yiyang; Hu, Junhua; Jia, Chuankun; Fu, Junwei; Li, Hongmei; Liu, Hui; Lin, Zhang; Li, Wenzhang; Li, Jiahang; Lu, Ying-Rui; Chan, Ting-Shan (2020-08-20). "Iron phthalocyanine with coordination induced electronic localization to boost oxygen reduction reaction". Nature Communications. 11 (1). doi:10.1038/s41467-020-18062-y. ISSN   2041-1723. PMC   7441147 . PMID   32820168.
  27. ↑ Mitra, Koushambi; Hartman, Matthew C. T. (2021). "Silicon phthalocyanines: synthesis and resurgent applications". Organic & Biomolecular Chemistry. 19 (6): 1168–1190. doi:10.1039/D0OB02299C. ISSN   1477-0520.
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