The Synthesis and Electroluminescence Properties of 4-Benzofuranyl-1,8-Naphthalimide Derivatives

Abstract:

A series of fluorescence compounds, 4-benzofuranyl-1,8-naphthalimides, were prepared through cycloaddition reaction from 4-ethynyl-1,8-naphthalimides and o-iodophenols which catalyzed by a Pd(PPh3)2Cl2 / CuI system under mild conditions. The intermediate material, 4-ethynyl-1,8- naphthalimide, was synthesized from 4-bromo-1,8- naphthalimide and trimethylsilyl- acetylene. The absorption and fluorescence spectra of 4-benzofuranyl-1,8- naphthalimides were studied and the quantum yields were measured. The maximum UV/vis absorption spectra were in the range of 375-400 nm and the maximum emission spectra were in the range of 470-510 nm. The electro- luminescent properties were also mensurated through a doped electroluminescent device which contains 1% 1,8-naphthalimides and 99% CBP (4,4'-N,N'-dicarbazole-biphenyl), It’s shown the maximum brightness reached 3700 cd/ m2 at 22.5V.

• Periodical: Advanced Materials Research (Volumes 557-559)
• Pages: 1031-1036
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.557-559.1031
• Online since: July 2012
• Authors: Jian Xin Yang*, Xiang Hui Wang
• Keywords: 1,8-Naphthalimide, Benzofuran, Electroluminescent Properties, Fluorescence Properties, Synthesis

References

[1] Qian X, Tang J, Zhang J, et al Synthesis of Furonaphthalimides with Potential Photosensitizing Biological Activity [J]. Dyes and Pigments 1994, 25 (2): 109-114

DOI: 10.1016/0143-7208(94)85042-9

[2] Konstantinova T N, Meallier P and Grabchev I. The Synthesis of 1,8-Naphthalic anhydride Derivatives as Dyes for Polymeric Materials [J]. Dyes and Pigments, 1993, 22 (3): 191-198

DOI: 10.1016/0143-7208(93)87006-z

[3] Grabchev I, Meallier P, Konstantinova TN, Popova M. Dyes and Pigments 1995; 28: 41.

[4] Robert S and Marie-jose A. Dyestuffs derived from naphthoylenebenzimidazoles. Fr:1493734, 1967, 9, 1

[5] Kamaladin G, Mokhtar A, Hajir B. Synthesis, spectral properties and application of novel monoazo disperse dyes derived from N-ester-1,8-naphthalimide to polyester[J] Dyes and Pigments 2008, 76: 684-689

DOI: 10.1016/j.dyepig.2007.01.024

[6] Jiang W, Sun Y M, Wang X L. Synthesis and photochemical properties of novel 4-diarylamine-1,8- naphthalimide derivatives [J] Dyes and Pigments 2008, 77: 125-128

DOI: 10.1016/j.dyepig.2007.03.017

[7] Donze J, L' Industrie Textile 1987; 1177: 519.

[8] Konstantinova TN, Meallier P, Grabchev I. Dyes and Pigments 1993; 22: 191.

[9] Nippon Kayaku. JP 1975; 18: 556.

[10] Grayshan PH, Peters AT. J Heterocyclic Chem 1973; 10: 699.

[11] Qian X, Tang J, Zhang J, Zhang Y. Dyes and Pigments 1994; 25: 109.

[12] Bojinov V B, Panova l P. Novel 4-(2,2,6,6-tetramethyl piperidin-4-ylamino)-1,8-naphthalimide based yellow-green emitting fluorescence sensors for transition metal ions and protons. Dyes and Pigments 2009; 80:61

DOI: 10.1016/j.dyepig.2008.05.007

[13] Arcadi A, Cacchi S, Marinelli F. Synthesis 1986; 749.

[14] Torii S, Xu LH, Okumoto H. Synlett 1992; 515-516.

[15] Larock RC, Yum EK, Doty MJ, Sham KKC. J Org Chem 1995; 60: 3270.

[16] Arcadi A, Cacchi S, Fabrizi G, Marinelli F, Moro L. Synlett 1999, 1432.

[17] Nan Y, Miao H, Yang Z. Org Lett 2000; 2: 297.

[18] Kabalka GW, Wang L, Pagni RM. Tetrahedron 2001; 57: 8017.

[19] Takahashi S, Kuroyama Y, Sonogashira K, Hagihara N. Synthesis 1980; 627.

[20] Olmsted P. J Phys Chem 1979; 83: 2581.