Perylenebisimide-based colorimetric and fluorescent sensors for selective detection of anions

Letters in Organic Chemistry

Volumn 7, Issue 6, 2010, Pages 495-501

  Guo, Peng ^a   Su, Xiaoyu ^a   Lan, Jingbo ^a  

^a Sichuan University   (China)

Author keywords

Anion recognition; Colorimetric and fluorometric detection; Hydrogen bonds; Imidazolium chemosensor; Perylenebisimide; Phenolic hydroxyl

Indexed keywords

EID: 78650378500     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017810791824928     Document Type: Article

References (41)

1. (a) de Silva, A.P.; Gunaratne, H.Q.N.; Gunnlaugsson, T.; Huxley, A.J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Signaling recognition events with fluorescent sensors and switches. Chem. Rev., 1997, 97, 1515.
2. (b) Martínez-Máñez, R.; Sancenón, F. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev., 2003, 103, 4419.
3. (c) Gale, P.A.; Garcia-Garrido, S.E.; Garric, J. Anion receptors based on organic frameworks: highlights from 2005 and 2006. Chem. Soc. Rev., 2008, 37, 151.
4. (d) Caltagirone, C.; Gale, P.A. Anion receptor chemistry: highlights from 2007. Chem. Soc. Rev., 2009, 38, 520.
5. (a) Chellappan, K.; Singh, N.J.; Hwang, I.C.; Lee, J.W.; Kim, K.S. A Calix[4]imidazolium[2]pyridine as an anion receptor. Angew. Chem. Int. Ed., 2005, 44, 2899.
6. (b) In, S.; Kang, J. Anion receptor with four imidazolium rings on the glycoluril. Tetrahedron Lett., 2005, 46, 7165.
7. (c) Kim, H.; Kang, J. Iodide selective fluorescent anion receptor with two methylene bridged bis-imidazolium rings on naphthalene. Tetrahedron Lett., 2005, 46, 5443.
8. (d) Ihm, H.; Yun, S.; Kim, H.G.; Kim, J.K.; Kim, K.S. Tripodal nitroimidazolium receptor for anion binding driven by (C-H)+-X-hydrogen bonds. Org. Lett., 2002, 4, 2897.
9. Yoon, J.; Kim, S.K.; Singh, N.J.; Kim, K.S. Imidazolium receptors for the recognition of anions. Chem. Soc. Rev., 2006, 35, 355.
10. (a) Kim, S.K.; Singh, N.J.; Kwon, J.; Hwang, I.C.; Park, S.J.; Kim, K.S.; Yoon, J. Fluorescent imidazolium receptors for the recognition of pyrophosphate. Tetrahedron, 2006, 62, 6065.
11. (b) Khatri, V.K.; Upreti, S.; Pandey, P.S. Novel bile acid-based cyclic bisimidazolium receptors for anion recognition. Org. Lett., 2006, 8, 1755.
12. (c) Singh, N.J.; Jun, E.J.; Chellappan, K.; Thangadurai, D.; Chandran, R.P.; Hwang, I.C.; Yoon, J.; Kim, K.S. Quinoxalineimidazolium receptors for unique sensing of pyrophosphate and acetate by charge transfer. Org. Lett., 2007, 9, 485.
13. (d) Niu, H.T.; Yin, Z.M.; Su, D.D.; Niu, D.; He, J.Q.; Cheng, J.P. Imidazoliumbased macrocycles as multisignaling chemosensors for anions. Dalton Trans., 2008, 3694.
14. (e) Willans, C.E.; Anderson, K.M.; Potts, L.C.; Steed, J.W. Allosteric effects in a tetrapodal imidazolium-derived calix[4]arene anion receptor. Org. Biomol. Chem., 2009, 7, 2756.
15. (f) Dinarès, I.; de Miguel, C.G.; Mesquida, N.; Alcalde, E. Bis(imidazolium)-Calix[4]arene receptors for anion binding. J. Org. Chem., 2009, 74, 482.
16. (g) Xu, Z. C.; Singh, N.J.; Lim, J.; Pan, J.; Kim, H.N.; Park, S.; Kim, K.S.; Yoon, J. Unique sandwich stacking of pyrene-adenine-pyrene for selective and ratiometric fluorescent sensing of ATP at physiological pH. J. Am. Chem. Soc., 2009, 131, 15528.
17. (a) Cormode, D.P.; Murray, S.S.; Cowley, A.R.; Beer, P.D. Sulfate selective anion recognition by a novel tetra-imidazolium zinc metalloporphyrin receptor. Dalton Trans., 2006, 5135.
18. (b) Khatri, V.K.; Chahar, M.; Pavani, K.; Pandey, P.S. Bile acid-based cyclic bisbenzimidazolium receptors for anion recognition: highly improved receptors for fluoride and chloride ions. J. Org. Chem., 2007, 72, 10224.
19. (c) Kim, S.K.; Seo, D.; Han, S.J.; Son, G.; Lee, I.J.; Lee, C.; Lee, K.D.; Yoon, J. A new imidazolium acridine derivative as fluorescent chemosensor for pyrophosphate and dihydrogen phosphate. Tetrahedron, 2008, 64, 6402.
20. (a) Ho, H.A.; Leclerc, M. New colorimetric and fluorometric chemosensor based on a cationic polythiophene derivative for iodide-specific detection. J. Am. Chem. Soc., 2003, 125, 4412.
21. (b) Kumar, S.; Luxami, V.; Kumar, A. Chromofluorescent probes for selective detection of fluoride and acetate ions. Org. Lett., 2008, 10, 5549.
22. (c) Lu, Q.S.; Dong, L.; Zhang, J.; Li, J.; Jiang, L.; Huang, Y.; Qin, S.; Hu, C.W.; Yu, X.Q. Imidazolium-functionalized BINOL as a multifunctional receptor for chromogenic and chiral anion recognition. Org. Lett., 2009, 11, 669.
23. (d) Mashraqui, S.H.; Betkar, R.; Chandiramani, M.; Quinonero, D.; Frontera, A. A novel fluoride selective optical chemosensor based on internal charge transfer signaling. Tetrahedron Lett., 2010, 51, 596.
24. (a) Boiocchi, M.; Boca, L.D.; Gomez, D.E.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. Nature of urea-fluoride interaction: incipient and definitive proton transfer. J. Am. Chem. Soc., 2004, 126, 16507.
25. (b) Cho, E.J.; Ryu, B.J.; Lee, Y.J.; Nam, K.C. Visible colorimetric fluoride ion sensors. Org. Lett., 2005, 7, 2607.
26. (c) Thangadurai, T.D.; Singh, N.J.; Hwang, I.C.; Lee, J.W.; Chandaran, R.P.; Kim, K.S. 2-Dimensional analytic approach for anion differentiation with chromofluorogenic receptors. J. Org. Chem., 2007, 72, 5461.
27. (d) Yeo, H.M.; Ryu, B.J.; Nam, K.C. A novel fluoride ion colorimetric chemosensor. Org. Lett., 2008, 10, 2931.
28. (e) Kim, D.S.; Chung, Y.M.; Jun, M.; Ahn, K.H. Selective colorimetric sensing of anions in aqueous media through reversible covalent bonding. J. Org. Chem., 2009, 74, 4849.
29. (a) Sugiyasu, K.; Fujita, N.; Shinkai, S. Visible-light-harvesting organogel composed of cholesterol-based perylene derivatives. Angew. Chem. Int. Ed., 2004, 43, 1229.
30. (b) Berberich, M.; Krause, A.M.; Orlandi, M.; Scandola, F.; Würthner, F. Toward fluorescent memories with nondestructive readout: photoswitching of fluorescence by intramolecular electron transfer in a diaryl etheneperylene bisimide photochromic system. Angew. Chem. Int. Ed., 2008, 47, 6616.
31. (c) Schmidt, R.; Oh, J.H.; Sun, Y.S.; Deppisch, M.; Krause, A.M.; Radacki, K.; Braunschweig, H.; Könemann, M.; Erk, P.; Bao, Z.; Würthner, F. High-performance air-stable nchannel organic thin film transistors based on halogenated perylene bisimide semiconductors. J. Am. Chem. Soc., 2009, 131, 6215.
32. Zhang, R.L.; Wang, Z.L.; Wu, Y.S.; Fu, H.B.; Yao, J.N. A novel redox-fluorescence switch based on a triad containing ferrocene and perylene diimide units. Org. Lett., 2008, 10, 3065.
33. (a) Chen, X.Q.; Jou, M.J.; Yoon, J. An "Off-On" type UTP/UDP selective fluorescent probe and its application to monitor glycosylation process. Org. Lett., 2009, 11, 2181.
34. (b) Zang, L.; Liu, R.C.; Holman, M.W.; Nguyen, K.T.; Adams, D.M. A singlemolecule probe based on intramolecular electron transfer. J. Am. Chem. Soc., 2002, 124, 10640.
35. (c) Guo, X.F.; Zhang, D.Q.; Zhu, D.B. Logic control of the fluorescence of a new dyad, spiropyranperylene diimide-spiropyran, with light, ferric ion, and proton: construction of a new three-input "AND" logic gate. Adv. Mater., 2004, 16, 125.
36. (d) Wang, B.; Yu, C. Fluorescence turn-on detection of a protein through the reduced aggregation of a perylene probe. Angew. Chem. Int. Ed., 2010, 49, 1485.
37. (a) Yang, L.; Qin, S.; Su, X.Y.; Yang, F.; You, J.S.; Hu, C.W.; Xie, R.G.; Lan, J.B. 1,1′-Binaphthyl-based imidazolium chemosensors for highly selective recognition of tryptophan in aqueous solutions. Org. Biomol. Chem., 2010, 8, 339.
38. (b) Chen, W.; Zhang, Y.Y.; Zhu, L.B.; Lan, J.B.; Xie, R.G.; You, J.S. A new concept of supported amino acid ionic liquids and their application in metal scavenging and heterogeneous catalysis. J. Am. Chem. Soc., 2007, 129, 13879.
39. (c) Luo, K.; Jiang, H.Y.; You, J.S.; Xiang, Q.X.; Guo, S.J.; Lan, J.B.; Xie, R.G. Chiral di-imidazolium molecular tweezers: synthesis and enantioselective recognition for amino acid derivatives. Lett. Org. Chem., 2006, 3, 363.
40. Kim, S.K.; Singh, N.J.; Kim, S.J.; Kim, H.G.; Kim, J.K.; Lee, J.W.; Kim, K.S.; Yoon, J. New fluorescent photoinduced electron transfer chemosensor for the recognition of H2PO4 -. Org. Lett., 2003, 5, 2083.
41. Feng, J.Q.; Liang, B.L.; Wang, D.L.; Wu, H.X.; Xue, L.; Li, X.Y. Synthesis and aggregation behavior of perylenetetracarboxylic diimide trimers with different substituents at bay positions. Langmuir, 2008, 24, 11209.