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Preparation of metalated azine complexes of iridium(III)

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Abstract

Arylaldazine and acetoneazine complexes [IrCl(η5-C5Me5){κ1-[N[double bond, length as m-dash]C(H)(R2C6H4)]–N[double bond, length as m-dash]C(H)(R2C6H4)}{P(OR1)3}]BPh4 (1, 2) and [IrCl(η5-C5Me5){κ1-[N[double bond, length as m-dash]C(CH3)2]–N[double bond, length as m-dash]C(CH3)2}{P(OR1)3}]BPh4 (3, 4) [R1 = Me (1, 3), Et (2, 4); R2 = H (a), 4-CH3 (b), 2,6-(CH3)2 (f)] were prepared by allowing chloro complexes IrCl25-C5Me5)[P(OR1)3] to react first with AgOTf and then with the appropriate azine. In solution, κ1-complexes 1–4 undergo a metalation reaction, affording chelate κ2-azine derivatives [Ir[upper bond 1 end]2-R2C6H3(H)C[double bond, length as m-dash]N[lower bond 1 start]–N[double bond, length as m-dash]C(H)(R2C6H4)}(η5-C5Me5){P(OR1)3}]BPh4 (5, 6) and [Ir[upper bond 1 start]2-CH2(CH3)C[double bond, length as m-dash]N[lower bond 1 start]–N[double bond, length as m-dash]C(CH3)2}(η5-C5Me5){P(OR1)3}]BPh4 (7, 8) [R1 = Me (5, 7), Et (6, 8); R2 = H (a), 4-CH3 (b), 4-CH3O (c); 4-F (d), 4-NO2 (e)]. The complexes were characterised spectroscopically and by X-ray crystal structure determination of [Ir[upper bond 1 end]2-C6H4(H)C[double bond, length as m-dash]N[lower bond 1 start]–N[double bond, length as m-dash]C(H)(C6H5)}(η5-C5Me5){P(OEt)3}]BPh4 (6a). Most of the κ2-arylazine derivatives showed photoluminescence properties upon excitation with near-UV and violet light, with emission peaks at around 650 nm. The photoluminescence features were rationalised according to DFT calculations.

Graphical abstract: Preparation of metalated azine complexes of iridium(iii)

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Publication details

The article was received on 21 Jun 2017, accepted on 28 Sep 2017 and first published on 09 Oct 2017


Article type: Paper
DOI: 10.1039/C7NJ02224G
Citation: New J. Chem., 2017, Advance Article
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    Preparation of metalated azine complexes of iridium(III)

    G. Albertin, S. Antoniutti, M. Bortoluzzi, J. Castro, F. Sibilla and E. Trave, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ02224G

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