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http://dx.doi.org/10.5012/bkcs.2013.34.5.1414

Synthesis of New Spiro[benzo[c]fluorene-7,9'-fluorene] Dimers and Their Optical Properties  

Seo, Jeong-A (Department of Nanobiomedical Science & WCU Research Center, Dankook University Graduate School)
Lee, Chil-Won (Department of Polymer Science and Engineering, Dankook University)
Gong, Myoung-Seon (Department of Nanobiomedical Science & WCU Research Center, Dankook University Graduate School)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.5, 2013 , pp. 1414-1420 More about this Journal
Abstract
Five novel spiro[benzo[c]fluorene-7,9'-fluorene] based dyes, including 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-5-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (7), 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-9-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (8), 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-2'-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (9), 9-[spiro[benzo[c]fluorene-7,9'-fluoren]-9-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (10), and 2'-[spiro[benzo[c]-fluorene-7,9'-fluoren]-2'-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (11) were successfully prepared from the corresponding halogen and boronic acid derivatives through the Suzuki coupling reaction, respectively. Chemical structures were confirmed by $^1H$ nuclear magnetic resonance (NMR), $^{13}C$ NMR, Fourier transforminfrared spectrscopy, mass spectroscopy, and elemental analysis. The thermal properties were determined by differential scanning calorimetry and thermal gravimetric analysis. The relationships between the optical and electrochemical properties and the combined positions between these dimers were systematically investigated using UV-vis, photoluminescence (PL), and photoelectron spectroscopy. These five dimers exhibited high fluorescent quantum yields and good morphological stability with high glass transition states > $174^{\circ}C$. Dimer 7 showed a UV absorbance peak at 353 nm, emission PL peak at 424 nm, and quantum efficiency of 0.62 in a cyclohexane solution.
Keywords
Spirodimer; Spiro[benzofluorene-fluorene]; High glass transition temperature; Blue host materials; OLED;
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1 Kim, K. S.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Org. Electron. 2008, 9, 797.   DOI   ScienceOn
2 Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99.   DOI   ScienceOn
3 Sirringhaus, H. Adv. Mater. 2005, 17, 2411.   DOI   ScienceOn
4 Ma, L. P.; Liu, J.; Yang, Y. Appl. Phys. Lett. 2002, 80, 2997.   DOI   ScienceOn
5 Bozano, L. D.; Kean, B. W.; Beinhoff, M.; Carter, K. R.; Rice, P. M.; Scott, J. C. Adv. Func. Mater. 2005, 15, 1933.   DOI   ScienceOn
6 Tang, C. W. Appl. Phys. Lett. 1986, 48, 183.   DOI   ScienceOn
7 Xue, J.; Uchida, S.; Rand, B. P.; Forrest, S. R. Appl. Phys. Lett. 2004, 85, 5757.   DOI   ScienceOn
8 Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T. Q.; Dante, M.; Heeger, A. J. Science 2007, 317, 222.   DOI   ScienceOn
9 Huo, L.; Hou, J.; Zhang, S.; Chen, H. Y.; Yang, Y. Angew. Chem. Int. Ed. 2010, 49, 1500.   DOI   ScienceOn
10 Jeon, S. O.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Org. Electron. 2008, 9, 522.   DOI   ScienceOn
11 Kim, K. S.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Org. Electron. 2008, 9, 797.   DOI   ScienceOn
12 Liu, F.; Xie, L.; Tang, C.; Liang, J.; Chen, Q. Q.; Peng, B.; Wei, W.; Cao, Y.; Huang, W. Org. Lett. 2009, 11, 3850.   DOI   ScienceOn
13 Kowada, T.; Yamaguchi, S.; Ohe, K. Org. Lett. 2010, 12, 296.   DOI   ScienceOn
14 Chiang, C. L.; Shu, C. F.; Chen, C. T. Org. Lett., 2005, 7, 3717.   DOI   ScienceOn
15 Jeon, Y. M.; Kim, W.; Lee, C. W.; Gong, M. S. Dyes Pigm. 2009, 83, 66.   DOI   ScienceOn
16 Jeon, S. O.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Synth. Met. 2009, 159, 1147.   DOI   ScienceOn
17 Chen, C. T.; Wei, Y.; Lin, J. S.; Moturu, M. V. R. K.; Chao, W. S.; Tao, Y. T.; Chien, C. H. J. Am. Chem. Soc. 2006, 128, 10992.   DOI   ScienceOn
18 Kim, J. H.; Jeon, Y. M.; Jang, J. G.; Ryu, S.; Chang, H. J.; Lee, C. W.; Kim, J. W.; Gong, M. S. Bull. Korean Chem. Soc. 2009, 30, 647.   DOI   ScienceOn
19 Jeon, S. O.; Lee, H. S.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Bull. Korean Chem. Soc. 2009, 30, 863.   DOI   ScienceOn
20 Kim, K. S.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Dyes Pigm. 2009, 81, 174.   DOI   ScienceOn
21 Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.   DOI   ScienceOn
22 Becke, A. D. J. Chem. Phys. 1993, 56, 48.
23 Frisch, M. J.; et al., GAUSSIAN 03, Revision B.05, Gaussian, Inc., Pittsburgh, PA, 2003.
24 Hamai, S.; Hirayama, F. J. Phys. Chem. 1983, 87, 83.   DOI
25 Cheon, J. W.; Lee, C. W.; Gong, M. S.; Geum, N. Dyes Pigments 2004, 61, 23.   DOI   ScienceOn
26 Liu, F.; Xie, L.; Tang, C.; Liang, J.; Chen, Q. Q.; Peng, B.; Wei, W.; Cao, Y.; Huang, W. Org. Lett. 2009, 11, 3850.   DOI   ScienceOn
27 Tang, C. W.; Van Slyke, S. A. Appl. Phys. Lett. 1987, 51, 913.   DOI
28 Baldo, M. A.; Thompson, M. E.; Forrest, S. R. Nature 2000, 403, 705.   DOI   ScienceOn
29 Jeon, S. O.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Org. Electron. 2008, 9, 522.   DOI   ScienceOn
30 Gong, M. S.; Lee, H. S.; Jeon, Y. M. J. Mater. Chem. 2010, 20, 10735.   DOI   ScienceOn