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. 1H NMR (CDCl3) 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 C26H15NO3S: 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 F2 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
참고문헌
- Dang, H. V.; Knobloch, B.; Habib, N. S.; Kappe, T.; Stadlbauer, W. J. Heterocyclic Chem. 2005, 42, 85. https://doi.org/10.1002/jhet.5570420112
- Dang, H. V.; Stadlbauer, W. J. Heterocyclic Chem. 2006, 43, 65. https://doi.org/10.1002/jhet.5570430110
- Shivachev, B.; Petrov, P.; Stoyanova, M. J. Chem. Crystallogr. 2009, 39, 209. https://doi.org/10.1007/s10870-008-9459-y
- Stadlbauer, W.; Dang, H. V.; Knobloch, B. W. J. Heterocyclic Chem. 2011, 48, 1039. https://doi.org/10.1002/jhet.600
- Lee, H.-S.; Kim, H.-J.; Kang, J.-G. Photochem. Photobio. Sci. 2011, 10, 1338. https://doi.org/10.1039/c1pp05045a
- Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997; Chapters 2 and 5.
- Steiner, T; Saenger, W. J. Am. Chem. Soc. 1992, 114, 10146. https://doi.org/10.1021/ja00052a009
- Frisch, M. J. T.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09 (Revision A. 02); Gaussian, Inc., Wallingford CT, 2009.
- Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112. https://doi.org/10.1107/S0108767307043930