7350-91-6Relevant academic research and scientific papers
Highly fluorescent complexes with gold, palladium or platinum linked to perylene through a tetrafluorophenyl group
Lentijo, Sergio,Aullon, Gabriel,Miguel, Jesus A.,Espinet, Pablo
, p. 6353 - 6365 (2013/07/26)
Treatment of 3-(1-hexynyl)perylene with Co2(CO)8 resulted in the formation of the dinuclear cobalt complex [Co 2(CO)6(μ-η2-C4H 9CC-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-PerC 6F4H) were prepared and used to synthesize [AuR(CN tBu)] (R = PerC6F42a), [AuR(CN(C 6H2)-3,4,5-(OC12H25)3)] (R = PerC6F4 (3a), R = C6-PerC 6F4 (3b)), trans-[PdR(PR′3)2X] (R = PerC6F4, R′ = Ph, X = I (4a)); (R = C 6-PerC6F4, R′ = Ph, X = I (4b)); (R = PerC6F4, R′ = Et, X = I (5a)); (R = C 6-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 A. 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.
A bichromophore based on perylene and terrylene for energy transfer studies at the single-molecule level
Schlichting, Peter,Duchscherer, Bettina,Seisenberger,Basche, Thomas,Braeuchle, Christoph,Muellen, Klaus
, p. 2388 - 2395 (2007/10/03)
A functionalized dialkylperylene and a modified terrylenetetracarboxdiimide (TTCDI) were joined together by a hexanediyl spacer. The resulting bichromophoric molecule 4 is a suitable model system for donor-acceptor energy transfer studies at the single-mo
New synthetic routes to alkyl-substituted and functionalized perylenes
Schlichting, Peter,Rohr, Ulrike,Muellen, Klaus
, p. 395 - 407 (2007/10/03)
3,9(10)-Dialkynyl- and 3-monoalkynyl-substituted perylenes (16 and 20) and their ω-functionalized derivatives 27, 30, 33, 35 can be synthesized easily and in high yields as well as the 3-alkyl-9(10)-alkynyl-substituted perylenes 39 and 42. This is achieved by a palladium-catalyzed coupling reaction of monobromoperylenes 19 and 38 and dibromoperylene 15 with 1-alkynes and ω-functionalized 1-alkynes, respectively. The quantitative conversion of the alkynes into the corresponding alkyl-substituted perylene derivatives 17, 21, 28, 31, 34, 36, 40 and 43 can be accomplished by catalytic hydrogenation. Further conversions of 28, 31, 34, 36, 40 and 43 provide the functionalized perylenes 29, 32, 37, 41 and 44. VCH Verlagsgesellschaft mbH, 1997.
