[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.12925/jkocs.2008.25.4.1

Synthesis of New N,N-Bis(5-acetylpyridin-2-yl)-phenylamine Derivatives and Their Solvatochromic Effects

El-Deeb, Ibrahim Mustafa (Department of Biomolecular Science, University of Science and Technology)
Lee, So-Ha (Life Sciences Research Division, Korea Institute of Science and Technology)

Publication Information

Journal of the Korean Applied Science and Technology / v.25, no.4, 2008 , pp. 411-417 More about this Journal

Abstract

A group of new N,N-bis(5-acetylpyridin-2-yl)phenylamine derivatives was synthesized in good yield applying an optimized Buchwald-Hartwig amination protocol. The synthesized compounds showed UV absorption maxima in the range of 320-360 nm, and showed good luminescence at dilute concentrations in the blue region of the spectra (in the range of 480-497 nm). They showed also a bathochromic shift associating the increase in solvent polarity. The synthesized compounds could be investigated for use in OLEDs or as potential monomers for PLEDs.

Keywords

Pyridine; triarylamine; photoinduced charge transfer; photoluminescence;

Citations & Related Records

Reference

1	Y. Lee, J. Kim. S. Kwon, C.-K. Min, Y. Yi, J. W. Kim, B. Koo, and M. Hong, Interface studies of aluminum, 8-hydroxyquinolatolithium (Liq) and $Alq_3$ for inverted OLED application. Org. Electron., 9, 407 (2008) DOI ScienceOn
2	S. Chen, X. Xu, Y. Liu, W. Qiu, G. Yu, H. Wang, and D. Zhu, New organic light-emitting materials: synthesis, thermal, pphotophysical, electrochemical, and electroluminescent properties. J. Phys. Chem. C, 111, 1029 (2007) DOI ScienceOn
3	D. C. G. Pinto, A. M. S. Silva, J. A. S. Cavalerio, and J. Elguero, New bis(chalcones) and their transformation into bis(pyrazoline) and bis(pyrazole) derivatives. Eur. J. Org. Chem., 4, 747 (2003)
4	J. B. Baell, R. W. Gable, A. J. Harvey, N. Toovey, T. Herzog, W. Hansel, and H. Wulff, Khellinone derivatives as blockers of the voltage-gated potassium channel Kv1.3: synthesis and immunosuppressive activity. J. Med. Chem., 47, 2326 (2004) DOI ScienceOn
5	Y. Sun, Y. N. C. Giebink, H. Kanno, B. Ma, M. E. Thompson, and S. R. Forrest, Management of singlet and triplet excitons for efficient white organic light-emitting devices. Nature, 440, 908 (2006) DOI ScienceOn
6	M. Hatanaka, K. Takahashi, S. Nakamura, and T. Mashino, Preparation and antioxidant activity of alpha-pyridoin and its derivatives. Bioorg. Med. Chem., 13, 6763 (2005) DOI ScienceOn
7	Y.-L. Liao, C.-Y. Lin, K.-T. Wong, T.-H. Hou, and W.-Y. Hung, A Novel ambipolar spirobifluorene derivative that behaves as an efficient blue-light emitter in organic light-emitting diodes. Org. Lett., 9, 4511 (2007) DOI ScienceOn
8	C.-H. Ku, C.-H. Kuo, C.-Y. Chen, M.-K. Leung, and K.-H. Hsieh, PLED devices containing triphenylamine-derived polyurethanes as hole-transporting layers exhibit high current efficiencies. J. Mater. Chem., 18, 1296 (2008) DOI ScienceOn
9	J. Kido, M. Kimura, and K. Nagai, Multilayer white light-emitting organic electroluminescent device. Science, 267, 1332 (1995) DOI ScienceOn
10	J.-S. Yang, Y.-D. Lin, Y.-H. Lin, and F.-L. Liao, Zn(II)-Induced ground-state ${\pi}$ -deconjugation and excited-state electron transfer in N,N-bis(2-pyridyl) amino-substituted arenes. J. Org. Chem., 69, 3517 (2004) DOI ScienceOn
11	D.-E. Kim, W.-S. Kim, B.-S. Kim, B.-J. Lee, and Y.-S. Kwon, Improvement of color purity in white OLED based on $Zn(HPB)_2$ as blue emitting layer. Thin Solid Films, 516, 3637 (2008) DOI ScienceOn
12	Z. Tan, R. Tang, F. Xi, and Y. Li, Synthesis, characterization, and electroluminescence of new conjugated PPV derivatives bearing triphenylamine side-chain through a vinylene bridge. Polym. Adv. Technol., 18, 963 (2007) DOI ScienceOn
13	I. M. El-Deeb, J. C. Ryu, and S. H. Lee, Synthesis of new N-arylpyrimidin-2-amine derivatives using a palladium catalyst. Molecules, 13, 818 (2008) DOI ScienceOn
14	J. Qiao, L. D. Wang, J. F. Xie, G. T. Lei, G. S. Wu, and Y. Qiu, Strongly luminescent binuclear aluminium chelate with polymer-like molecular packing and solution-processibility. Chem. Commun., 36, 4560 (2005)
15	O. Navarro, N. Marion, N. M. Scott, J. Gonzalez, D. Amoroso, A. Bell, and S. P. Nolan, Synthesis of novel (NHC)Pd(acac)Cl complexes (acac = acetylacetonate) and their activity in cross-coupling reactions. Tetrahedron, 61, 9716 (2005) DOI ScienceOn
16	T.-I. Ho, A. Elangovan, H.-Y. Hsu, and S.-W. Yang, Highly fluorescent N,N-dimethylaminophenylethynylarenes: synthesis, photophysical properties, and electrochemiluminescence. J. Phys. Chem. B, 109, 8626 (2005) DOI ScienceOn
17	J. A. Mikroyannidis, K. M. Gibbons, A. P. Kulkarni, and S. A. Jenekhe, Poly(fluorenevinylene) copolymers containing bis(phenyl)oxadiazole and triphenylamine moieties: synthesis, photophysics, and redox and electroluminescent properties. Macromolecules, 41, 663 (2008) DOI ScienceOn
18	T. Miyazaki, M. Nishiyama, and N. Matsumoto, Production of arylamines in presence of palladium catalyst. U.S. Pat. Appl. Publ., US 2007282111 A1 (2007)