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2012 , Vol. 70 >Issue 10: 1187 - 1192

DOI: https://doi.org/10.6023/A1112153

研究论文

2,5-二(4'-羧基苯基)-1-苯基吡咯对胺的“点亮”荧光检测

  • 韩天宇 ,
  • 董一帆 ,
  • 李则宇 ,
  • 佟斌 ,
  • 石建兵 ,
  • 支俊格 ,
  • 董宇平
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  • a 北京理工大学材料科学与工程学院 北京 100081;
    b 北京理工大学化学学院 北京 100081

收稿日期: 2011-12-15

  修回日期: 2012-02-16

  网络出版日期: 2012-02-28

基金资助

国家自然科学基金(Nos. 51073026, 51061160500, 21074011)和高等学校博士学科点科研基金(No. 20091101110031)资助项目.

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“Turn-on” Fluorescent Detection of 2,5-Di(4'-carboxylphenyl)-1-phenylpyrrole to Amines

  • Han Tianyu ,
  • Dong Yifan ,
  • Li Zeyu ,
  • Tong Bin ,
  • Shi Jianbing ,
  • Zhi Junge ,
  • Dong Yuping
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  • a College of Materials Science and Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing, 100081;
    b College of Chemistry, Beijing Institute of Technology, Beijing 100081

Received date: 2011-12-15

  Revised date: 2012-02-16

  Online published: 2012-02-28

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 51073026, 51061160500, 21074011) and the Research Fund for the Doctoral Program of Higher Education (No. 20091101110031).

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摘要

基于水溶性2,5-二(4'-羧基苯基)-1-苯基吡咯的羧酸钠盐(TPP-2COONa)具有质子化荧光淬灭、去质子化荧光增强的特征. 在研究了TPP-2COONa 的紫外吸收光谱和荧光发射光谱对pH 的响应规律的同时, 以此为荧光探针, 证实了TPP-2COOH 对于多种胺类(氨水、二异丙胺、异丙胺和三乙胺)荧光增强响应明显, 而对芳香胺(吡咯、苯胺、吡啶)没有任何荧光响应, 其中对于氨水最为敏感, 在很窄的pH 区间和低浓度范围内荧光强度大幅度增长, 体现了该探针对于氨水具有良好的选择性和灵敏度, 并可简易实现“在线裸眼检测”.

关键词： 三苯基吡咯; “点亮”检测; 荧光探针; 胺; 水溶性

本文引用格式

韩天宇 , 董一帆 , 李则宇 , 佟斌 , 石建兵 , 支俊格 , 董宇平 . 2,5-二(4'-羧基苯基)-1-苯基吡咯对胺的“点亮”荧光检测[J]. 化学学报, 2012 , 70(10) : 1187 -1192 . DOI: 10.6023/A1112153

Abstract

2,5-Di(4'-carboxylphenyl)-1-phenylpyrrole was firstly successfully synthesized. UV-Vis and fluorescence spectra were employed to study the optical properties of TPP-2COONa at different pH values in aqueous media. The compound is found to weaken fluorescence in acidic state and, however, strengthen fluorescence in base state. The experimental results indicated that the fluorescent emission of TPP-2COOH can be “turned-on” by ammonia and some water-soluble alkyl amines (triethylamine, isopropylamine, diisopropylamine). But it remains unchanged upon addition of N-containing aromatic compounds (aniline, pyrrole, and pyridine). Specially, the compound as the fluorescent probe shows the good selectivity and sensitivity toward ammonia. Thus, the “on-line naked eye” detection for amines becomes possible.

Key words： triphenylpyrrole; turn-on detection; fluorescent probe; amine; water-soluble

参考文献

1 Lawrence, S. A. Amines: Synthesis, Properties and Applications, Cambridge University Press, Cambridge, 2004.
2 Wyers, G. P.; Otjes, R. P.; Slamina, J. Atmos. Environ.1993, 27A, 2085.  
3 Boardman, G. D.; Starbuck, S. M.; Hudgins, D. B.; Li, X. Y.; Kuhn, D. D. Environ. Toxicol. 2004, 19, 134.  
4 Schuler, D. J.; Boardman, G. D.; Kuhn, D. D.; Flick, G. J. J. World Aquacult. Soc. 2010, 41, 438.  
5 Kalogianni, E.; Alexis, M.; Tsangaris, C.; Abraham, M.; Bonga, S. E. W.; Iger, Y.; van Ham, E. H.; Stoumboudi, M. T. J. Fish Biol. 2011, 78, 4.
6 Faff, L.; Reichenbach, A.; Albrecht, J. J. Neurosci. Res.1996, 46, 231.
7 Walker, V. Diabetes Obes. Metab. 2009, 11, 823.  
8 Adams, M. B.; Powell, M. D.; Purser, G. J. J. Fish Biol.2001, 58, 848.  
9 Zhang, J.; Wang, S. R.; Xu, M. J.; Wang, Y.; Xia, H. J.; Zhang, S. M.; Guo, X. Z.; Wu, S. H. J. Phys. Chem. C 2009,113, 1662.  
10 Lahdesmaki, I.; Lewenstam, A.; Ivaska, A. Talanta 1996,43, 125.  
11 Hernandez, S. C.; Chaudhuri, D.; Chen, W.; Myung, N. V.; Mulchandani, A. Electroanalysis 2007, 19, 2125.  
12 Nanto, H.; Minami, T.; Takata, S. J. Appl. Phys. 1986, 60,482.
13 Rao; G. S. T.; Rao, D. T. Sens. Actuators B 1999, 55, 166.  
14 Wagh, M. S.; Jain, G. H.; Patil, D. R.; Patil S. A.; Patil, L. A. Sens. Actuators B 2006, 115, 128.  
15 Dikovska, A. O.; Atanasov, P. A.; Andreev, A. T.; Zafirova, B. S.; Karakoleva, E. I.; Stoyanchov, T. R. Appl. Surf. Sci.2007, 254, 1087.  
16 Sagade, A. A.; Sharma, R. Sens. Actuators B 2008, 133,135.  
17 Bekyarova, E.; Kalinina, I.; Itkis, M. E.; Beer, L.; Cabrera, N.; Haddon, R. C. J. Am. Chem. Soc. 2007, 129, 10700.  
18 Battie, Y.; Ducloux, O.; Thobois, P.; Susi, T.; Kauppinen, E. I.; Loiseau, A. Phys. Status Solidi B 2011, 248, 2462.  
19 Preininger, C.; Mohr, G. J.; Klimant, I.; Wolfbies, O. S. Anal. Chim. Acta 1996, 334, 113.  
20 Chen, X.; Dai, Y. J.; Li, Z.; Zhang, Z. X.; Wang, X. R. Fresenius J. Anal. Chem. 2001, 370, 1048.  
21 Waich, K.; Mayr, T.; Klimant, I. Talanta 2008, 77, 66.  
22 Che, Y.; Yank, X.; Loser, S.; Zang, L. Nano Lett. 2008, 8,2219.  
23 Waich, K.; Mayr, T.; Klimant, I. Meas. Sci. Technol. 2007,18, 3195.  
24 Chen, X. B.; Xi, H. T.; Sun, X. Q.; Zhao, T.; Meng, Q.; Jiang, Y. Chin. J. Org. Chem. 2011, 31, 544 (in Chinese). (陈晓冰, 席海涛, 孙小强, 赵婷, 孟启, 姜艳, 有机化学, 2011, 31, 544.)
25 Li, N.; Liu, M. L.; Yin, W. T.; Yang, Z.; Li, J. L.; Shi, Z. Chin. J. Org. Chem. 2011, 31, 39 (in Chinese). (李娜, 刘美玲, 尹文婷, 杨征, 李剑利, 史真, 有机化学,2011, 31, 39.)
26 Liu, G.; Shao, J. Acta Chim. Sinica 2011, 69, 1070 (in Chinese). (刘阁, 邵杰, 化学学报, 2011, 69, 1070.)
27 Peng, L. H.; Wang, M.; Zhang, J. X.; Zhang, D. Q.; Zhu, D. B. Org. Lett. 2009, 11, 1943.  
28 Shi, J. B.; Cai, L. P.; Pu, K. Y.; Liu, B. Chem. Asian J.2010, 5, 301.  
29 Liu, Y.; Tang, Y.; Barashkov, N. N.; Irgibaeva, I. S.; Lam, J. W. Y.; Hu, R.; Birimzhanova, D.; Yu, Y.; Tang, B. Z. J. Am. Chem. Soc. 2010, 132, 13951.  
30 Sanji, T.; Shiraishi, K.; Tanaka, M. ACS Appl. Mater. Interfaces2009, 1, 270.  
31 Thomas, S. W.; Joly, G. D.; Swager, T. M. Chem. Rev.2007, 107, 1339.  
32 Takagai, Y.; Nojiri, Y.; Takase, T.; Hinze, W. L.; Butsugan, M.; Igarashid, S. Analyst 2010, 135, 1417.  
33 Fan, L. J.; Jones, W. E. J. Am. Chem. Soc. 2006, 128, 6784.  
34 Germain, M. E.; Knapp, M. J. Inorg. Chem. 2008, 47, 9748.  
35 Ryu, D.; Park, E.; Kim, D. S.; Yan, S.; Lee, J. Y.; Chang, B. Y.; Ahn, K. H. J. Am. Chem. Soc. 2008, 130, 2394.  
36 Vaidya, S.; Schmehl, R. H. New J. Chem. 2012, 36, 52.
37 Feng, X.; Tong, B.; Shen, J. B.; Shi, J. B.; Han, T. Y.; Chen, L.; Zhi, J. G.; Lu, P.; Ma, Y. G.; Dong, Y. P. J. Phys. Chem. B 2010, 114, 16731.  
38 Han, T. Y.; Feng, X.; Tong, B.; Shi, J. B.; Chen, L.; Zhi, J. G.; Dong, Y. P. Chem. Commun. 2012, 48, 416.  
39 Xu, H. L.; Tong, B.; Shi, J. B.; Liu, Y.; Tian, X. L.; Zhi, J. G.; Dong, Y. P.; Lam, J. W. Y.; Tang, B. Z. Acta Polym. Sinica 2007, (3), 293 (in Chinese). (徐宏丽, 佟斌, 石建兵, 刘暘, 田旭玲, 支俊格, 董宇平, Lam J. W. Y., 唐本忠, 高分子学报, 2007, (3), 293.)
40 Birks, J. B. In Photophysics of Aromatic Molecules, Wiley, London, 1970.
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