Issue

Vol. 26 No. 6 (2014): Vol 26 Issue 6

Copyright (c) 2014 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

A New Pyrene Derivative Based on L-Shaped Tröger's Base for Non-Doped Organic Blue Light-Emitting Diodes

https://doi.org/10.14233/ajchem.2014.17354
Zuo-Qin Liang
Jiangsu Key Laboratory for Environment Functional Materials, School of Chemistry Biology and Material Engineering, Suzhou University of Science and Technology, Suzhou 215009, P.R. China ;State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, P.R. China
Xiao-Mei Wang
Jiangsu Key Laboratory for Environment Functional Materials, School of Chemistry Biology and Material Engineering, Suzhou University of Science and Technology, Suzhou 215009, P.R. China
Yu-Yang Zhou
Jiangsu Key Laboratory for Environment Functional Materials, School of Chemistry Biology and Material Engineering, Suzhou University of Science and Technology, Suzhou 215009, P.R. China
Zeng-Ze Chu
Department of Polymer Science and Engineering, College of Chemistry, Peking University, Beijing 100871, P.R. China
Xu-Tang Tao
State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, P.R. China
De-Chun Zou
Department of Polymer Science and Engineering, College of Chemistry, Peking University, Beijing 100871, P.R. China

Corresponding Author(s) : Zuo-Qin Liang

zuoqinliang@mail.usts.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 6 (2014): Vol 26 Issue 6

Abstract

A novel pyrene derivative, 2,8-di(1-pyrenyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (TBPy), was synthesized and well characterized. The structure was confirmed with 1H NMR, 13C NMR and MS analyses. Its photophysical, thermal, electrochemical and electroluminescent properties as well as the electronic structure were investigated. The compound shows good thermal stability, high fluorescence yield and high hole-transport ability. The organic light-emitting diode using TBPy as an emitter layer exhibits a blue emission at 485 nm. Therefore, it is a promising candidate for fabricating efficient blue organic light-emitting diodes.

Keywords

Pyrene Tröger's base L-Shaped Organic light-emitting diodes
Liang, Z.-Q., Wang, X.-M., Zhou, Y.-Y., Chu, Z.-Z., Tao, X.-T., & Zou, D.-C. (2014). A New Pyrene Derivative Based on L-Shaped Tröger’s Base for Non-Doped Organic Blue Light-Emitting Diodes. Asian Journal of Chemistry, 26(6), 1781–1785. https://doi.org/10.14233/ajchem.2014.17354
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. C.W. Tang and S.A. VanSlyke, Appl. Phys. Lett., 51, 913 (1987); doi:10.1063/1.98799.
  2. J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. Mackay, R.H. Friend, P.L. Burns and A.B. Holmes, Nature, 347, 539 (1990); doi:10.1038/347539a0.
  3. R.H. Friend, R.W. Gymer, A.B. Holmes, J.H. Burroughes, R.N. Marks, C. Taliani, D.D.C. Bradley, D.A.D. Santos, J.L. Brdas, M. Lgdlund and W.R. Salaneck, Nature, 397, 121 (1999); doi:10.1038/16393.
  4. B.W. D’Andrade and S.R. Forrest, Adv. Mater., 16, 1585 (2004); doi:10.1002/adma.200400684.
  5. L. Duan, L.D. Hou, T.W. Lee, J. Qiao, D.Q. Zhang, G.F. Dong, L.D. Wang and Y. Qiu, J. Mater. Chem., 20, 6392 (2010); doi:10.1039/b926348a.
  6. K.H. Lee, C.S. Son, J.Y. Lee, S. Kang, K.S. Yook, S.O. Jeon, J.Y. Lee and S.S. Yoon, Eur. J. Org. Chem., 4788 (2011); doi:10.1002/ejoc.201100472.
  7. J.R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum, New York (1999).
  8. N. Karl, Synth. Met., 133-134, 649 (2003); doi:10.1016/S0379-6779(02)00398-3.
  9. L. Zöphel, D. Beckmann, V. Enkelmann, D. Chercka, R. Rieger and K. Müllen, Chem. Commun. (Camb.), 47, 6960 (2011); doi:10.1039/c1cc11827g.
  10. K.A. Zachariasse, Trends Photochem. Photobiol., 3, 211 (1994).
  11. Z.Q. Liang, Z.Z. Chu, D.C. Zou, X.M. Wang and X.T. Tao, Org. Electron., 13, 2898 (2012); doi:10.1016/j.orgel.2012.08.041.
  12. C. Poriel, N. Cocherel, J. Rault-Berthelot, L. Vignau and O. Jeannin, Chem. Eur. J., 17, 12631 (2011); doi:10.1002/chem.201100790.
  13. X.M. Liu, C.B. He, J.C. Huang and J.M. Xu, Chem. Mater., 17, 434 (2005); doi:10.1021/cm048719j.
  14. T.M. Figueira-Duarte, P.G. Del Rosso, R. Trattnig, S. Sax, E.J.W. List and K. Müllen, Adv. Mater., 22, 990 (2010); doi:10.1002/adma.200902744.
  15. J. Tröger, J. Prakt. Chem., 36, 225 (1887); doi:10.1002/prac.18870360123.
  16. A. Tatibouët, M. Demeunynck, C. Andraud, A. Collet and J. Lhomme, Chem. Commun., 23, 161 (1999); doi:10.1039/a808822e.
  17. Y. Kubo, T. Ohno, J.- Yamanaka, S. Tokita, T. Iida and Y. Ishimaru, J. Am. Chem. Soc., 123, 12700 (2001); doi:10.1021/ja0113448.
  18. N.R. Deprez, K.A. McNitt, M.E. Petersen, R.G. Brown and D.E. Lewis, Tetrahedron Lett., 46, 2149 (2005); doi:10.1016/j.tetlet.2005.01.166.
  19. C.L. Ramírez, R. Procaccini, C.A. Chesta, A.R. Parise and D.M.A. Vera, Org. Electron., 14, 2564 (2013); doi:10.1016/j.orgel.2013.06.024.
  20. C.X. Yuan, Q. Xin, H.J. Liu, L. Wang, M.H. Jiang and X.T. Tao, Sci. China Chem., 54, 587 (2011); doi:10.1007/s11426-011-4224-z.
  21. Q. Xin, X.-T. Tao, F.-Z. Wang, J.-L. Sun, D.-C. Zou, F.-J. Wang, H.-J. Liu, Z. Liu, Y. Ren and M.-H. Jiang, Org. Electron., 9, 1076 (2008); doi:10.1016/j.orgel.2008.08.013.
  22. C.X. Yuan, X.T. Tao, Y. Ren, Y. Li, J.X. Yang, W.T. Yu, L. Wang and M.H. Jiang, J. Phys. Chem. C, 111, 12811 (2007); doi:10.1021/jp0711601.
  23. H. Xi, C.X. Yuan, Y.X. Li, Y. Liu and X.T. Tao, CrystEngComm, 14, 2087 (2012); doi:10.1039/c2ce06260g.
  24. J. Jensen, M. Strozyk and K. Wärnmark, J. Heterocycl. Chem., 40, 373 (2003); doi:10.1002/jhet.5570400230.
  25. J.Y. Hu, M.M. Era, R.J. Elsegood and T. Yamato, Eur. J. Org. Chem., 2010, 72 (2010); doi:10.1002/ejoc.200900806.
  26. K.C. Wu, P.J. Ku, C.S. Lin, H.T. Shih, F.I. Wu, M.J. Huang, J.J. Lin, I.-C. Chen and C.H. Cheng, Adv. Funct. Mater., 18, 67 (2008); doi:10.1002/adfm.200700803.
  27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fu-kuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven and J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009.
  28. J.G.C. Veinot and T.J. Marks, Acc. Chem. Res., 38, 632 (2005); doi:10.1021/ar030210r.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0