A fluorescent color/intensity changed chemosensor for Fe 3+ by photo-induced electron transfer (PET) inhibition of fluoranthene derivative

Dyes and Pigments

Volumn 94, Issue 1, 2012, Pages 60-65

  Li, Zhanxian ^a   Zhang, Lifeng ^a   Li, Xiaoya ^a   Guo, Yongkai ^a   Ni, Zhonghai ^c   Chen, Jianhong ^b   Wei, Liuhe ^a   Yu, Mingming ^a,b  

^a ZHENGZHOU UNIVERSITY   (China)

^b TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

^c CHINA UNIVERSITY OF MINING AND TECHNOLOGY   (China)

Author keywords

Fe 3+ sensor; Fluoranthene; Fluorescence signal restore; Fluorescent chemosensor; Photo induced electron transfer; Selectivity

Indexed keywords

BLUE SHIFT; CHEMOSENSOR; CRYSTAL DATA; DETECTION LIMITS; FLUORANTHENE; FLUORESCENCE SIGNAL RESTORE; FLUORESCENCE SIGNALS; FLUORESCENCE STUDIES; FLUORESCENT COLORS; FLUORESCENT EMISSION; FLUORESCENT INTENSITY; HIGH SELECTIVITY; O-PHENANTHROLINE; PHOTO-INDUCED ELECTRON TRANSFER;

BEHAVIORAL RESEARCH; CATALYST SELECTIVITY; ELECTRON TRANSITIONS; METAL IONS; PHYSIOLOGY; RESTORATION; SENSORS;

FLUORESCENCE;

EID: 84055179009     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.11.007     Document Type: Article

References (55)

1. B. Valeur, and I. Leray Design principles of fluorescent molecular sensors for cation recognition Coord Chem Rev 205 2000 3 40
2. J.B. Pawley Handbook of biological confocal microscopy 1995 Plenum New York
3. J.W. Lichtman, and J.A. Conchello Fluorescence microscopy Nat Methods 2 2005 910 919 (Pubitemid 43108727)
4. J. Wu, W. Liu, J. Ge, H. Zhang, and P. Wang New sensing mechanisms for design of fluorescent chemosensors emerging in recent years Chem Soc Rev 40 2011 3483 3495
5. 2+ and pyrophosphate anion Macromolecules 43 2010 739 744
6. 2+-selective fluorescence sensor: synthesis, mechanisms, and applications in living cells J Am Chem Soc 131 2009 2008 2012
7. D.W. Domaille, L. Zeng, and C.J. Chang Visualizing ascorbate-triggered release of labile copper within living cells using a ratiometric fluorescent sensor J Am Chem Soc 132 2010 1194 1195
8. M. Kumar, A. Dhir, and V. Bhalla A molecular keypad lock based on the thiacalix[4]arene of 1,3-alternate conformation Org Lett 11 2009 2567 2570
9. 2+ ion-induced self-assembly of pyrenylquinoline with a pyrenyl excimer formation Org Lett 11 2009 3378 3381
10. Y. Zhou, F. Wang, Y. Kim, S. Kim, and J. Yoon Cu2+-Selective ratiometric and "Off-On" sensor based on the rhodamine derivative bearing pyrene group Org Lett 11 2009 4442 4445
11. H.J. Kim, J. Hong, A. Hong, S. Ham, J.H. Lee, and J.S. Kim Cu2+-induced intermolecular Static excimer formation of pyrenealkylamine Org Lett 10 2008 1963 1966
12. + detection Org Lett 10 2008 5015 5018
13. 2+ and its application to MCF-7 cells Chem Commun 2010 7169 7171
14. L. Xue, C. Liu, and H. Jiang A ratiometric fluorescent sensor with a large Stokes shift for imaging zinc ions in living cells Chem Commun 2009 1061 1063
15. C.E. Felton, L.P. Harding, J.E. Jones, B.M. Kariuki, S.J.A. Pope, and C.R. Rice A wavelength and lifetime responsive cryptate-containing fluorescent probe for zinc ions in water Chem Commun 2008 6185 6187
16. H.H. Wang, Q. Gan, X.J. Wang, L. Xue, S.H. Liu, and H. Jiang A water-soluble, small molecular fluorescent sensor with femtomolar sensitivity for zinc ion Org Lett 9 2007 4995 4998
17. J.S. Wu, W.M. Liu, X.Q. Zhuang, F. Wang, P.F. Wang, and S.L. Tao Fluorescence turn on of coumarin derivatives by metal cations: a new signaling mechanism based on C=N isomerization Org Lett 9 2007 33 36
18. H.Y. Gong, Q.Y. Zheng, X.H. Zhang, D.X. Wang, and M.X. Wang Methylazacalix[4]pyridine: En route to Zn(2+)-specific fluorescence sensors Org Lett 8 2006 4895 4898
19. M.A. Palacios, Z. Wang, V.A. Montes, G.V. Zyryanov, and P. Anzenbacher Rational design of a minimal size sensor array for metal ion detection J Am Chem Soc 130 2008 10307 10314
20. Z. Xu, K.H. Baek, H.N. Kim, J. Cui, X. Qian, and D.R. Spring Zn(2+)-triggered amide tautomerization produces a highly Zn(2+)-selective, cell-permeable, and ratiometric fluorescent sensor J Am Chem Soc 132 2010 601 610
21. 2+ fluorescent sensor derived from 2-(pyridin-2-yl)benzoimidazole with ratiometric sensing potential Org Lett 11 2009 795 798
22. Y. Zhang, X. Guo, W. Si, L. Jia, and X. Qian Ratiometric and water-soluble fluorescent zinc sensor of carboxamidoquinoline with an alkoxyethylamino chain as receptor Org Lett 10 2008 473 476
23. 2+ J Am Chem Soc 127 2005 10107 10111 (Pubitemid 41001443)
24. F. Zapata, A. Caballero, A. Espinosa, A. Tàrraga, and P. Molina Triple channel sensing of Pb(II) ions by a simple multiresponsive ferrocene receptor having a 1-deazapurine backbone Org Lett 10 2008 41 44
25. Y. Xiang, A. Tong, and Y. Lu Abasic site-containing DNAzyme and aptamer for label-free fluorescent detection of Pb(2+) and adenosine with high sensitivity, selectivity, and tunable dynamic range J Am Chem Soc 131 2009 15352 15357
26. E.M. Nolan, and S.J. Lippard Tools and tactics for the optical detection of mercuric ion Chem Rev 108 2008 3443 3480
27. M.H. Lee, S.W. Lee, S.H. Kim, C. Kang, and J.S. Kim Nanomolar Hg(II) detection using Nile blue chemodosimeter in biological media Org Lett 11 2009 2101 2104
28. J. Du, J. Fan, X. Peng, P. Sun, J. Wang, and H. Li A new fluorescent chemodosimeter for Hg(2+): selectivity, sensitivity, and resistance to cys and GSH Org Lett 12 2010 476 479
29. Y. Zhou, C.Y. Zhu, X.S. Gao, X.Y. You, and C. Yao Hg(2+)-selective ratiometric and "Off-On" chemosensor based on the azadiene-pyrene derivative Org Lett 12 2010 2566 2569
30. M. Suresh, A.K. Mandal, S. Saha, E. Suresh, A. Mandoli, and R. Di Liddo Azine-based receptor for recognition of Hg(2+) ion: crystallographic evidence and imaging application in live cells Org Lett 12 2010 5406 5409
31. M. Zhang, Y.H. Gao, M.Y. Li, M.X. Yu, F.Y. Li, and L. Li A selective turn-on fluorescent sensor for FeIII and application to bioimaging Tetrahedron Lett 48 2007 3709 3712 (Pubitemid 46656277)
32. J. Mao, L. Wang, W. Dou, X. Tang, Y. Yan, and W. Liu Tuning the selectivity of two chemosensors to Fe(III) and Cr(III) Org Lett 9 2007 4567 4570
33. N.C. Lim, S.V. Pavlova, and C. Brückner Squaramide hydroxamate-based chemidosimeter responding to iron(III) with a fluorescence intensity increase Inorg Chem 48 2009 1173 1182
34. J.L. Bricks, A. Kovalchuk, C. Trieflinger, M. Nofz, M. Büschel, and A.I. Tolmachev On the development of sensor molecules that display Fe-III-amplified fluorescence J Am Chem Soc 127 2005 13522 13529 (Pubitemid 41401203)
35. M. Xu, S. Wu, F. Zeng, and C. Yu Cyclodextrin supramolecular complex as a water-soluble ratiometric sensor for ferric ion sensing Langmuir 26 2010 4529 4534
36. A.J. Weerasinghe, C. Schmiesing, S. Varaganti, G. Ramakrishna, and E. Sinn Single-and multiphoton turn-on fluorescent Fe(3+) sensors based on bis(rhodamine) J Phys Chem B 114 2010 9413 9419
37. H.J. Jung, N. Singh, D.Y. Lee, and D.O. Jang Single sensor for multiple analytes: chromogenic detection of I(-) and fluorescent detection of Fe(3+) Tetrahedron Lett 51 2010 3962 3965
38. N. Singh, N. Kaur, J. Dunn, M. MacKay, and J.F. Callan A new fluorescent chemosensor for iron(III) based on the beta-aminobisulfonate receptor Tetrahedron Lett 50 2009 953 956
39. L. Praveen, M.L.P. Reddy, and R.L. Varma Dansyl-styrylquinoline conjugate as divalent iron sensor Tetrahedron Lett 51 2010 6626 6629
40. M. Kumar, R. Kumar, and V. Bhalla Optical chemosensor for Ag(+), Fe(3+), and cysteine: information processing at molecular level Org Lett 13 2011 366 369
41. 2+-selective anthracene-based fluorescent PET sensor with tridentate ionophore of amide/β-amino alcohol J Fluoresc 17 2007 383 389 (Pubitemid 47146070)
42. P. Aisen, M. Wessling-Resnick, and E.A. Leibold Iron metabolism Curr Opin Chem Biol 3 1999 200 206 (Pubitemid 29145787)
43. B.F. Matzanke, G. Muller-Matzanke, and K.N. Raymond Iron carriers and iron proteins vol. 5 1989 VCH Publishers New York
44. R.B. Lauffer Iron and human disease 1992 CRC Press Boca Raton, FL
45. Z.Y. Xia, J.H. Su, H.H. Fan, K.W. Cheah, H. Tian, and CH. Che Multifunctional diarylamine-substituted benzo[k]fluoranthene derivatives as green electroluminescent emitters and nonlinear optical materials J Phys Chem C 114 2010 11602 11606
46. Z.X. Li, L. Zhang, L.N. Wang, Y.K. Guo, L.H. Cai, and M.M. Yu Highly sensitive and selective fluorescent sensor for Zn(2+)/Cu(2+) and new approach for sensing Cu(2+) by central metal displacement Chem Commun 47 2011 5798 5800
47. 3+ Inorg Chem Commun 14 2011 1656 1658
48. B.J. Kim, and J.Y. Chang Preparation of carbon nanospheres from diblock copolymer micelles with cores containing curable acetylenic groups Macromolecules 39 2006 90 94 (Pubitemid 43112725)
49. S. Setayesh, A.C. Grimsdale, T. Weil, V. Enkelmann, K. Müllen, and F. Meghdadi Polyfluorenes with polyphenylene dendron side chains: toward non-aggregating, light-emitting polymers J Am Chem Soc 123 2001 946 953 (Pubitemid 32151373)
50. F. Morgenroth, and K. Müllen Dendritic and hyperbranched polyphenylenes via a simple Diels-Alder route Tetrahedron 53 1997 15349 15366 (Pubitemid 27465839)
51. X. Xu, S. Chen, G. Yu, C. Di, H. You, and D. Ma High-efficiency blue light-emitting diodes based on a polyphenylphenyl compound with strong electron-accepting groups Adv Mater 19 2007 1281 1285 (Pubitemid 46942263)
52. 3+ and its application to MCF-7 cells Tetrahedron 67 2011 7096 7100
53. R.C. Chiechi, R.J. Tseng, F. Marchioni, Y. Yang, and F. Wudl Efficient blue-light-emitting electroluminescent devices with a robust fluorophore: 7,8,10-triphenylfluoranthene Adv Mater 18 2006 325 328 (Pubitemid 43213247)
54. M. Velusamy, K.R.J. Thomas, C.H. Chen, J.T. Lin, Y.S. Wen, and W.T. Hsieh Synthesis, structure and electroluminescent properties of cyclometalated iridium complexes possessing sterically hindered ligands Dalton Trans 2007 3025 3034 (Pubitemid 47152313)
55. J.N. Demas, and G.A. Grosby Measurement of photoluminescence quantum yields Review J Phys Chem 75 1971 991 1024