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Structural and Luminescence Properties of 6-Oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl thiophene-2-carboxylate
Structural and Luminescence Properties of 6-Oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl thiophene-2-carboxylate
Bulletin of the Korean Chemical Society. 2014. Oct, 35(10): 3111-3114
Copyright © 2014, Korea Chemical Society
  • Received : March 28, 2014
  • Accepted : June 18, 2014
  • Published : October 20, 2014
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About the Authors
Yong-Kwang Jeong
Min-Ah Kim
Hyo-Sung Lee
Sung Woo Lee
Center for Research Facilities, Chungnam National University, Yuseong-gu, Daejeon 305-764, Korea
Jun-Gill Kang

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Experimental
Synthesis of OPPCT. HPPCO was synthesized from carbazole (8.35 g, 0.05 mol) and diethyl phenylmalonate (14.15 g, 0.06 mol) according to Method A described in Ref. 1 . A mixture of HPPCO (3.1 g, 10 mmol) and potassium carbonate (1.38 g, 10 mmol) was dissolved in acetone (300 mL). To the greenish acetone solution, 2-thiophenecarbonyl chloride (1.61 g, 11 mmol) was added and stirred at room temperature for 3 h. The orange powder was filtered and then dissolved in a 1:1 chloroform and water mixed solvent (200 mL). The organic phase was separated and dried over anhydrous magnesium sulfate. The precipitate was obtained by evaporating the solvent and then was washed several times with hexane. 1 H NMR (CDCl 3 ) δ 1H, d, 8.73 ( J = 8 Hz), 1H, d, 8.16 ( J = 8 Hz), 1H, d, 8.08 ( J = 8 Hz), 1H, d, 7.87 ( J = 4 Hz), 1H, d, 7.68 ( J = 8 Hz), 1H, d, 7.66 ( J = 4 Hz), 1H, t, 7.59 ( J = 8 Hz), 4H, m, 7.55-7.51, 1H, t, 7.50 ( J = 8 Hz), 2H, t, 7.38 ( J = 8 Hz), 1H, t, 7.31 ( J = 8 Hz), 1H, d, 7.13 ( J = 4 Hz). Anal. found: C, 72.7; H, 3.3; N, 3.7; O, 12.2; S, 6.6. Calcd. for C 26 H 15 NO 3 S: C, 74.1; H, 3.6; N, 3.3; O, 11.4; S, 7.6.
X-ray Crystallograpy. Single crystals of OPPCT were grown from dichloromethane solution using the slowevaporation method. Diffraction data were collected at room temperature on a Bruker SMART CCD diffractometer using graphite monochromated Mo Kα radiation. The structure was solved by applying the direct method using SHELXS-97 and refined by a full-matrix least-squares calculation on F 2 using SHELXL-97. 9 All non-H atoms were refined with anisotropic displacement parameters. Hydrogen atoms were fixed at ideal geometric positions, and their contributions were included in the structural factor calculations. The crystal data and refinement results are listed in Table S4. Crystallographic data for the structure reported here have been deposited with CCDC (Deposition No. CCDC-993939). These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html or from CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, E-mail:deposit@ccdc.cam.ac.uk.
Optical Measurements. The absorption spectra, the luminescence and the excitation spectra, the luminescence quantum yield, and the luminescence decay time were measured using previously described methods. 5
Acknowledgements
This research was supported by National Research Foundation (NRF-2012R1A1A2007201).Supporting Information.Geometric parameters from X-ray data and optimized calculation (Table S1), molecular orbitals (Table S2), details of CIS excited states (Table S3), and crystal data and refinement (Table S4) are included in supporting information.
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