| 光谱学与光谱分析 |
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| Study on Synthesis and Relation between Structure and Optical Properties of Stilbene Derivatives |
| XU Hong-yao1,2, WU Lei2,HU Lei2 |
1. College of Material Science and Engineering & State Key Laboratory for Modification of Chemical Fibers and Polymeric Materials, Donghua University, Shanghai 201620, China
2. School of Chemistry and Chemical Engineering, Anhui University, Hefei 230039, China |
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Abstract In the present paper, three stilbene derivatives with different substitutions were synthesized by phase-transfer Wittig reaction and Pd(Ⅱ)-catalyzed heck reaction. The molecular structures were characterized by FTIR, elemental analysis and 1H NMR spectra. The authors investigated the influence of molecular structure on electron absorption spectra and luminescence-emitting properties. The results show that compared with that of compound 3a without substitution with a maximum electron absorption peak at 356 nm, the substitution of CH3 group results in a slightly red-shift of electron absorption peak wavelength of molecules to 358 nm, while the substitution of NO2 group makes molecule possess larger π electron conjugation and the maximum absorption peak shifts to a longer wavelength region (388 nm). Simultaneously, it was found that the substitution of CH3 group yields luminescence emission with a peak wavelength at 414 nm and the luminescence emission strength significantly increases in comparison with that of compound 3a without substitution. On the contrary, the substitution of electron-acceptor NO2 group results in the decrease in luminescence emission strength with an emission maximum wavelength at 525 nm. Therefore, the structure of substitution on stilbene molecules has an important effect on their optical properties and this will provide some foundation for the structure design of emitting molecules in future.
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Received: 2007-06-08
Accepted: 2007-09-19
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Corresponding Authors:
XU Hong-yao
E-mail: hongyaoxu@dhu.edu.cn
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[1] Wang X M, Zhou Y F, Yu W T, et al. J. Mater. Chem.,2000, 10: 2698.
[2] Drobizhev M, Karotki A, Dzenis Y, et al. J. Phys. Chem. B,2003, 107: 7540.
[3] Shiyanovskaya I, Hepel M. J. Electrochem. Soc., 1998, 145: 1023.
[4] Deak W, Strickler J H, Webb W W. Science, 1990, 145: 1023.
[5] Albota M, Beljonne D, Bredas L J, et al.Science, 1998,281:1653.
[6] Reinhardt B A, Brott L L, Clarson S J, et al. Chem. Mater., 1998, 10: 1863.
[7] Rumi M, Ehrlich J E, Marder S R, et al. J. Am. Chem. Soc.,2000, 122: 9500.
[8] Cumpston B H, Ananthavel S P, et al. Nature, 1999, 398: 51.
[9] SHI Qin-fen, WANG Xiao-mei, JIANG Wan-li, et al(施琴芬，王筱梅，蒋宛莉，等). Spectroscopy and Spectral Analysis(光谱学与光谱分析),2005,25(12): 1925.
[10] Yin S C, Xu H Y, Su X Y, et al. J. Polymer Science: Part A, Polymer Chemistry,2006, 44: 2346.
[11] WANG Shao-ting, YANG Yong-li, ZHU Hui-ju, et al(王少亭，杨永丽，朱惠菊, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析),2006,26(5): 933.
[12] Iwase Y, Kamada K, Ohta K, et al. J. Mater. Chem.,2003, 13: 1575.
[13] Belfield K D, Chinna C, Schafer K J. Tetrahedron Lett., 1997, 38: 6131.
[14] Ding N, Li Y X, Chu S D. Chinese J. Org. Chem.,2004,24(8): 898.
[15] Eddarir S, Abdelhadi Z, Rolando C. Tetrahedron Lett.,2001, 42: 9127.
[16] YIN Shou-chun, XU Hong-yao, TANG Ben-zhong(尹守春，徐洪耀，唐本忠). Chinese Journal of Applied Chemistry(应用化学)，2004,21(10): 973.
[17] XU Hong-yao, SHEN Juan, GUANG Shan-yi, et al(徐洪耀，沈 娟，光善仪，等). Chinese Journal of Synthetic Chemistry(合成化学)，2006，14(1)：14.
[18] Nicholas E L, Bonnie J T. Tetrahedron Lett.,2003, 44: 8653.
[19] CHEN Guo-zhen, HUANG Xian-zhi, ZHENG Zhu-zi, et al(陈国珍，黄贤智，郑朱梓，等).Fluorescence Analysis Method(荧光分析法). Beijing: Science Press(北京：科学出版社)，2006. 7. |
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