Tris(8-hydroxyquinolinato)aluminium

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Tris(8-hydroxyquinolinato)aluminium
AlumQ3.svg
Names
IUPAC name
Tris(8-hydroxyquinolinato)aluminium
Other names
8-Hydroxyquinoline aluminium salt, Alq3, aluminium 8-hydroxyquinolinate, aluminium oxinate,
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.570 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-227-0
PubChem CID
UNII
  • InChI=1S/3C9H7NO.Al.9H/c3*11-8-5-1-3-7-4-2-6-10-9(7)8;;;;;;;;;;/h3*1-6,11H;;;;;;;;;;/p-3 Yes check.svgY
    Key: HLONXFDEFIQTRK-UHFFFAOYSA-K Yes check.svgY
  • InChI=1/3C9H7NO.Al.9H/c3*11-8-5-1-3-7-4-2-6-10-9(7)8;;;;;;;;;;/h3*1-6,11H;;;;;;;;;;/p-3/rC27H27AlN3O3/c1-7-19-10-4-16-29-25(19)22(13-1)32-28(29,30-17-5-11-20-8-2-14-23(33-28)26(20)30)31-18-6-12-21-9-3-15-24(34-28)27(21)31/h1-18H,28H9/q-3
    Key: HLONXFDEFIQTRK-AOGCTXLYAD
  • c7ccc8cccc9O[AlH3-6]36(Oc2cccc1ccc[n+]3c12)(Oc5cccc4ccc[n+]6c45)[n+]7c89
Properties
C27H18AlN3O3
Molar mass 459.43
AppearanceYellow powder
Melting point > 300 °C (572 °F; 573 K)
insoluble in water
Hazards
GHS pictograms GHS-pictogram-exclam.svg
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tris(8-hydroxyquinolinato)aluminium is the chemical compound with the formula Al(C9H6NO)3. Widely abbreviated Alq3, it is a coordination complex wherein aluminium is bonded in a bidentate manner to the conjugate base of three 8-hydroxyquinoline ligands.

Contents

Structure

Both the meridional and facial isomers are known as well as several polymorphs (different crystalline forms). [1]

Mer-tris(8-hydroxyquinoline)aluminium(III)-from-xtal-2000-CM-3D-ellipsoids.png Fac-tris(8-hydroxyquinoline)aluminium(III)-from-xtal-2003-CM-3D-ellipsoids.png
Thermal ellipsoid model of mer-Alq3 [2] Thermal ellipsoid model of fac-Alq3 [3]

Synthesis

The compound is prepared by the reaction of 8-hydroxyquinoline with aluminium(III) sources [4]

Al3+ + 3 C9H7NO → Al(C9H6NO)3 + 3 H+

Applications

Alq3 is a common component of organic light-emitting diodes (OLEDs). Variations in the substituents on the quinoline rings affect its luminescence properties. [5]

Related Research Articles

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Potassium ferrioxalate, also called potassium trisoxalatoferrate or potassium tris(oxalato)ferrate(III) is a chemical compound with the formula K
3
[Fe(C
2
O
4
)
3
]. It often occurs as the trihydrate K
3
[Fe(C
2
O
4
)
3
]·3H2O
. Both are crystalline compounds, lime green in colour.

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3
COCHCOCH
3
) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring. The simplest complexes have the formula M(acac)3 and M(acac)2. Mixed-ligand complexes, e.g. VO(acac)2, are also numerous. Variations of acetylacetonate have also been developed with myriad substituents in place of methyl (RCOCHCOR′). Many such complexes are soluble in organic solvents, in contrast to the related metal halides. Because of these properties, acac complexes are sometimes used as catalyst precursors and reagents. Applications include their use as NMR "shift reagents" and as catalysts for organic synthesis, and precursors to industrial hydroformylation catalysts. C
5
H
7
O
2
in some cases also binds to metals through the central carbon atom; this bonding mode is more common for the third-row transition metals such as platinum(II) and iridium(III).

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3
CO
2
)
3
. Under standard conditions it appears as a white, water-soluble solid that decomposes on heating at around 200 °C. The triacetate hydrolyses to a mixture of basic hydroxide / acetate salts, and multiple species co-exist in chemical equilibrium, particularly in aqueous solutions of the acetate ion; the name aluminium acetate is commonly used for this mixed system.

References

  1. Cölle, M.; Dinnebier, R. E.; Brütting, W. (2002). "The structure of the blue luminescent δ-phase of tris(8-hydroxyquinoline)aluminium(III) (Alq3)". Chemical Communications. 2002 (23): 2908–9. doi:10.1039/b209164j. PMID   12478807.
  2. Brinkmann, M.; Gadret, G.; Muccini, M.; Taliani, C.; Masciocchi, N.; Sironi, A. (2000). "Correlation between Molecular Packing and Optical Properties in Different Crystalline Polymorphs and Amorphous Thin Films of mer-Tris(8-hydroxyquinoline)aluminum(III)". J. Am. Chem. Soc. 122 (21): 5147–57. doi:10.1021/ja993608k.
  3. Rajeswaran, M.; Blanton, T. N.; Klubek, K. P. (2003). "Refinement of the crystal structure of the δ-modification of tris(8-hydroxyquinoline)aluminum(III), δ-Al(C9H6NO)3, the blue luminescent Alq3". Zeitschrift für Kristallographie – New Crystal Structures. 218 (4): 439–40. doi: 10.1524/ncrs.2003.218.jg.471 .
  4. Katakura, R.; Koide, Y. (2006). "Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-hydroxyquinolinate)aluminum (Alq3)". Inorg. Chem. 45 (15): 5730–2. doi:10.1021/ic060594s. PMID   16841973.
  5. Montes, V. A.; Pohl, R.; Shinar, J.; Anzenbacher, P. Jr. (2006). "Effective Manipulation of the Electronic Effects and Its Influence on the Emission of 5-Substituted Tris(8-quinolinolate) Aluminum(III) Complexes". Chemistry: A European Journal. 12 (17): 4523–35. doi:10.1002/chem.200501403. PMID   16619313.