Tris(8-hydroxyquinolinato)aluminium

Tris(8-hydroxyquinolinato)aluminium
Names
	IUPAC name Tris(8-hydroxyquinolinato)aluminium
	Other names 8-Hydroxyquinoline aluminium salt, Alq3, aluminium 8-hydroxyquinolinate, aluminium oxinate,
Identifiers
CAS Number	2085-33-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	21106485 ;
ECHA InfoCard	100.016.570
UNII	6DP9L7516L ;
	InChI InChI=1S/3C9H7NO.Al.9H/c311-8-5-1-3-7-4-2-6-10-9(7)8;;;;;;;;;;/h31-6,11H;;;;;;;;;;/p-3 Key: HLONXFDEFIQTRK-UHFFFAOYSA-K ; InChI=1/3C9H7NO.Al.9H/c311-8-5-1-3-7-4-2-6-10-9(7)8;;;;;;;;;;/h31-6,11H;;;;;;;;;;/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;
	SMILES c7ccc8cccc9O[AlH3-6]36(Oc2cccc1ccc[n+]3c12)(Oc5cccc4ccc[n+]6c45)[n+]7c89;
Properties
Chemical formula	C27H18AlN3O3
Molar mass	459.43
Appearance	Yellow powder
Melting point	> 300 °C (572 °F; 573 K)
Solubility in water	insoluble in water
	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.

Structure

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


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 C₉H₆NOH → 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]

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References

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.
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.
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.
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.
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.

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[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.