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Volumn 13, Issue 5, 2010, Pages 613-617

Synthesis, crystal structure and photophysical properties of a novel Pt(II) complex with multi-functionalized cyclometalating ligand

Author keywords

Crystal structure; Cyclometalated; Multi functionalized; Photophysics; Platinum (II)

Indexed keywords


EID: 77952209197     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2010.02.016     Document Type: Article
Times cited : (7)

References (26)
  • 15
    • 77952168634 scopus 로고    scopus 로고
    • Synthesis of 9-(4-Bromobutane)carbazole (1, To a mixture of KOH (11.2 g) and nBu4NBr in H2O (20 mL) was added dropwise a solution of carbazole (6.68 g, 40.0 mmol) and 1, 4-dibromobutane (20 mL, 160 mmol) in THF (80 mL, and the mixture was refluxed for 18 h. After the mixture was cooled to room temperature, the product was extracted with dichloromethane, washed with distilled water, and dried over anhydrous sodium sulfate and concentrated. The product mixture was purified by column chromatography (silica gel, petroleum ether, CH2Cl2, 2:1 (V/V, 9-(4-bromobutane)carbazole was obtained as white needle crystal by recrystallizing from MeOH/Ethyl Acetate solution: 9.5 g (yield: 78.5, 1H NMR (300 MHz, CDCl3, δ 8.10 (d, J, 7.8 Hz, 2H, 7.49-7.38 (m, 4H, 7.26-7.12 (m, 2H, Ar, 4.38 (t, J, 6.9 Hz, 2H, 3.38 (t, J, 6.4 Hz, 2H, 2.07 (m, 2H, 1.92 (m, CH2, 13C NMR 75 MHz, CDCl3, δ 140.2, 125.7, 122.9, 12
    • 2-). Anal. Calcd for C16H16BrN: C, 63.59; H, 5.34; N, 4.63. Found: C, 63.38; H, 5.25; N, 4.43%.
  • 18
    • 77952116966 scopus 로고    scopus 로고
    • Synthesis of Ligand HL (3, 4-(p-Bromophenyl)-6-phenyl-2, 2′-bipyridine (1.94 g, 5.0 mmol, palladium acetate (13.0 mg, 0.06 mmol) and DPEphos (45.0 mg, 0.08 mmol) were charged into a flask and purged with argon. Aniline (1.0 mL, 10.7 mmol) was added via syringe, followed by toluene (20 ml, NaOBut (0.81 g, 8.5 mmol) was added in one portion. The reaction mixture was heated to 80 °C under stirring for 12 h. The solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane, washed with distilled water, and dried over anhydrous sodium sulfate and concentrated. The residue was dissolved in THF (60 mL, NaH (2.5 g, > 52, in mineral oil) was added and purged with argon. The reaction mixture was stirred for 1 h at room temperature, and then 9-(4-bromobutane)carbazole (6.04 g, 20.0 mmol) was added dropwise via syringe. After the solution was refluxed until the conversion was complete as monitored by thin layer chromatography, it was cooled
    • 2-). Anal. Calcd for C44H36N4: C, 85.13; H, 5.85; N, 9.03. Found: C, 84.92; H, 5.67; N, 8.62%.
  • 19
    • 77952199604 scopus 로고    scopus 로고
    • Synthesis of Pt(II) complex (4, A mixture of HL (0.32 g, 0.5 mmol, K2PtCl4 (0.21 g, 0.5 mmol) and glacial acetic acid (30 mL) was refluxed for 24 h under a nitrogen atmosphere in the absence of light. The reaction mixture was then cooled to room temperature and filtered. The obtained solid was recrystallized from MeOH/CH2Cl2 solution twice to form the desired product as red crystal: 0.35 g (yield: 82.4, 1H NMR (300 MHz, CDCl3, δ 8.89 (d, J, 5.1 Hz, 1H, 8.68 (d, J, 8.1 Hz, 1H, 8.38 (s, 1H, 8.34 (t, J, 7.8 Hz, 1H, 8.14 (d, J, 7.8 Hz, 2H, 8.12 (d, J, 5.4 Hz, 1H, 7.92 (d, J, 8.7 Hz, 2H, 7.88 (t, J, 6.6 Hz, 1H, 7.75 (d, J, 7.5 Hz, 1H, 7.59 (d, J, 8.1 Hz, 1H, 7.50-7.36 (m, 5H, 7.21-7.04 (m, 8H, 6.85 (d, J, 8.7 Hz, 2H, Ar, 4.42 (t, J, 6.9 Hz, 2H, 3.80 (t, J, 6.9 Hz, 2H, 1.88 (m, 2H, 1.72 m, 2H,-CH2, Anal. Calcd for C44H35ClN4Pt: C, 62.15; H, 4.15; N, 6.59. Found: C, 61.67; H, 4.11; N, 6
    • 2-). Anal. Calcd for C44H35ClN4Pt: C, 62.15; H, 4.15; N, 6.59. Found: C, 61.67; H, 4.11; N, 6.28%.
  • 20
    • 77952162440 scopus 로고    scopus 로고
    • Diffraction data was collected on a Bruker SMART APEX II CCD diffractometer equipped with a graphite-monochromated Mo-Kα radiation (λ, 0.71073 Å) at 296(2) K using a Φ-ω scan mode in the range of 2.38 ≤ θ ≤ 25.00°. A total of 17497 reflections including 6130 unique ones were collected, of which 6101 were observed [I > 2σ I, and used in structure solution. The intensity data were corrected by Lp factors and empirical absorption The structure was solved by direct methods and subsequent successive difference Fourier maps, and refined by full-matrix least-squares techniques on F2. All of the non-hydrogen atoms were refined anisotropically. The organic hydrogen atoms were generated geometrically
    • 2. All of the non-hydrogen atoms were refined anisotropically. The organic hydrogen atoms were generated geometrically.


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