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Issue 18, 2013
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Highly fluorescent complexes with gold, palladium or platinum linked to perylene through a tetrafluorophenyl group

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Abstract

Treatment of 3-(1-hexynyl)perylene with Co2(CO)8 resulted in the formation of the dinuclear cobalt complex [Co2(CO)6(μ–η2-C4H9C[triple bond, length as m-dash]C-Per)] (Per = 3-perylenyl) (1). The perylene derivatives 3-(2,3,5,6-tetrafluorophenyl)perylene (PerC6F4H) and 3-(2,3,5,6-tetrafluorophenyl)-9(10)hexylperylene (C6-PerC6F4H) were prepared and used to synthesize [AuR(CNtBu)] (R = PerC6F42a), [AuR(CN(C6H2)-3,4,5-(OC12H25)3)] (R = PerC6F4 (3a), R = C6-PerC6F4 (3b)), trans-[PdR(PR′3)2X] (R = PerC6F4, R′ = Ph, X = I (4a)); (R = C6-PerC6F4, R′ = Ph, X = I (4b)); (R = PerC6F4, R′ = Et, X = I (5a)); (R = C6-PerC6F4, R′ = Et, X = I (5b)); (R = PerC6F4, R′ = Ph, X = NCS (6a)), and trans-[Pd(PerC6F4)(PEt3)2X] (X = Br (7a); X = I (8a)). The molecular structure of complexes 1, 2a, and 6a has been determined by X-ray diffraction analysis. The perylenyl fragments of complexes 2a or 6a are essentially planar and make dihedral angles to the tetrafluorophenyl plane of 57.49° (2a) and 77.75° (6a). No π–π stacking of perylenyl rings is observed in any of the three molecules, but 2a shows association of two monomers (arranged almost antiparallel), with an Au⋯Au distance of 3.114 Å. DFT calculations were performed on the absorption spectra of representative PerC6F4Y (Y = H, F, Au(CNMe), PtBr(PMe3)2 and PdBr(PMe3)2). All complexes exhibit fluorescence associated with the perylene fragment with emission quantum yields, in solution at room temperature, in the range 0.20–0.90 and emission lifetimes ∼4 ns, and no significant differences in the emission maxima, due to an efficient electronic decoupling of the metal fragment from the HOMO and LUMO of the perylene chromophore. The latter is confirmed by DFT calculations.

Graphical abstract: Highly fluorescent complexes with gold, palladium or platinum linked to perylene through a tetrafluorophenyl group

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Publication details

The article was received on 27 Nov 2012, accepted on 09 Jan 2013 and first published on 10 Jan 2013


Article type: Paper
DOI: 10.1039/C3DT32843K
Dalton Trans., 2013,42, 6353-6365

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    Highly fluorescent complexes with gold, palladium or platinum linked to perylene through a tetrafluorophenyl group

    S. Lentijo, G. Aullón, J. A. Miguel and P. Espinet, Dalton Trans., 2013, 42, 6353
    DOI: 10.1039/C3DT32843K

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