Citation: Zhi-Yun Dong, Da-Wei Zhang, Xiao-Zhi Jiang, Hui Li, Guo-Hua Gao. A viologen-urea-based anion receptor： Colorimetric sensing of dicarboxylate anions[J]. Chinese Chemical Letters, ;2013, 24(8): 688-690. shu

A viologen-urea-based anion receptor： Colorimetric sensing of dicarboxylate anions

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a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China;
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b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Corresponding author: Hui Li, Guo-Hua Gao,
Received Date: 22 March 2013
Available Online: 19 April 2013

Compound 1 bearing urea and viologen groups has been designed and synthesized. It could be used as a colorimetric receptor for dicarboxylate anions due to the significant color changes of the solution upon the addition of dicarboxylates. More importantly, the color changes were related to the chain lengths of the dicarboxylates tested. UV-vis, ¹H NMR and HRMS studies demonstrated that receptor 1 utilized hydrogen bonds and electrostatic interactions to form 1:1 stoichiometry complexes with these anions. In addition, the generation of cation radical 1⁺ during the complexation process was also detected by EPR.
- Colorimetric receptor,
- Urea,
- Viologen,
- Dicarboxylate
1. [1]
  [1] M. Wenzel, J.R. Hiscock, P.A. Gale, Anion receptor chemistry: highlights from 2010, Chem. Soc. Rev. 41 (2012) 480-520.
2. [2]
  [2] X.B. Zhou, Y.W. Yip, W.H. Chan, A.W.M. Lee, An easy assembled fluorescent sensor for dicarboxylates and acidic amino acids, Beilstein J. Org. Chem. 7 (2011) 75-81.
3. [3]
  [3] S.J. Dickson, E.V.B. Wallace, A.N. Swinburne, et al., Intramolecular binding site competition as a means of tuning the response of a colourimetric anion sensor, New J. Chem. 32 (2008) 786-789.
4. [4]
  [4] P.M.S. Monk, N.M. Hodgkinson, Charge-transfer complexes of the viologens: effects of complexation and the rate of electron transfer to methyl viologen, Electrochim. Acta 3-4 (1998) 245-255.
5. [5]
  [5] P.M.S. Monk, N.M. Hodgkinson, R.D. Partridge, The colours of charge-transfer complexes of methyl viologen: effects of donor, ionic strength and solvent, Dyes Pigments 43 (1999) 241-251.
6. [6]
  [6] J.J. Park, Y.H. Kim, S. Rhim, J. Kang, Anion receptors with viologen molecular scaffold, Tetrahedron Lett. 53 (2012) 247-252.
7. [7]
  [7] T.M. Bockman, J.K. Kochi, Isolation and oxidation-reduction of methyl viologen cation radicals. Novel disproportionation in charge-transfer salts by X-ray crystallography, J. Org. Chem. 55 (1990) 4127-4135.
8. [8]
  [8] K. Ghosh, G. Masanta, A.P. Chattopadhyay, Triphenylamine-based pyridine Noxide and pyridinium salts for size-selective recognition of dicarboxylates, Eur. J. Org. Chem. 45 (2009) 15-4524.
9. [9]
  [9] Z.W. Xu, J. Tang, H. Tian, A highly sensitive colorimetric and ratiometric sensor for fluoride ion, Chin. Chem. Lett. 19 (2008) 1353-1357.
10. [10]
  [10] J.C. Waterton, J.K.M. Sanders, Hyperfine coupling in chlorophyll radical cations. A nuclear magnetic resonance approach, J. Am. Chem. Soc. 100 (1978) 4044-4049.
11. [11]
  [11] C. Kong, L. Qin, J. Liu, et al., Determination of dissolved oxygen based on photoinduced electron transfer from quantum dots to methyl viologen, Anal. Methods 2 (2010) 1056-1062.
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沈阳化工大学材料科学与工程学院沈阳 110142