An imidazole-containing core-substituted naphthalene diimide: Fluorescent sensing properties toward copper ion and optimized selectivity by tuning the solvent medium

Sensors and Actuators, B: Chemical

Volumn 207, Issue PartA, 2015, Pages 827-832

  Li, Nana ^a   Zong, Luyi ^a   Li, Qianqian ^a   Li, Zhen ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

Chemosensor; Cu2+; Imidazole; Naphthalendiimide; Selectivity; Solvent medium

Indexed keywords

CATALYST SELECTIVITY; COPPER; FLUORESCENCE; METAL IONS; ORGANIC POLYMERS; SILICA; SILICA GEL; SOLVENTS;

CHEMOSENSOR; EMISSION WAVELENGTH; FLUORESCENCE SENSORS; FLUORESCENT SENSING; IMIDAZOLE; NAPHTHALENDIIMIDE; NAPHTHALENE DIIMIDE; SELECTIVITY AND SENSITIVITY;

NAPHTHALENE;

EID: 84955344873     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2014.10.118     Document Type: Article

References (44)

1. B. Valeur, and I. Leray Design principles of fluorescent molecular sensors for cation recognition Coord. Chem. Rev. 205 2000 3 40
2. 2+ displacement approach Tetrahedron 66 2010 1678 1683
3. K. Rurack, and U. Resch-Genger Rigidization, preorientation and electronic decoupling - the magic triangle for the design of highly efficient fluorescent sensors and switches Chem. Soc. Rev. 31 2002 116 127
4. Z. Guo, W. Chen, and X. Duan Highly selective visual detection of Cu(II) utilizing intramolecular hydrogen bond-stabilized merocyanine in aqueous buffer solution Org. Lett. 12 2010 2202 2205
5. D. Maity, A.K. Manna, D. Karthigeyan, T.K. Kundu, S.K. Pati, and T. Govindaraju Visible-near-infrared fluorescent copper sensors based on julolidine conjugates: selective detection and fluorescence imaging in living cells Chem. Eur. J. 17 2011 11152 11161
6. 2+ based on thiourea-salicylaldehyde coordination in aqueous media Chem. Eur. J. 17 2011 1410 1414
7. 2+ ions Sens. Actuators B 173 2012 580 584
8. R. Uauy, M. Olivares, and M. Gonzalez Essentiality of copper in humans Am. J. Clin. Nutr. 67 1998 952s 959s
9. 2+ ion with nanomolar detection limit and its application in live cell imaging Inorg. Chem. Commun. 25 2012 26 29
10. Z. Yang, C. Yan, Y. Chen, C. Zhu, C. Zhu, C. Zhang, X. Dong, W. Yang, Z. Guo, Y. Lu, and W. He A novel terpyridine/benzofurazan hybrid fluorophore: metal sensing behavior and application Dalton Trans. 40 2011 2173 2176
11. A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher, and T.E. Rice Signaling recognition events with fluorescent sensors and switches Chem. Rev. 97 1997 1515 1566
12. Z. Xu, Y. Xiao, X. Qian, J. Cui, and D. Cui Ratiometric selective fluorescent sensor for Cu(II) based on internal charge transfer (ICT) Org. Lett. 7 2005 889 892
13. 2+ and its application in live cell imaging Chem. Eur. J. 14 2008 6892 6900
14. 2+ ions: fast, selective, and highly sensitive Angew. Chem. Int. Ed. 37 1998 772 773
15. 2+-Selective fluorescent chemosensor based on coumarin and its application in bioimaging Dalton Trans. 40 2011 10815 10817
16. K.M.K. Swamy, S.K. Kwon, H.N. Lee, C. Mao, J.M. Kim, K.H. Lee, J. Kim, I. Shin, and J. Yoon Boronic acid-linked fluorescent and colorimetric probes for copper ions Chem. Commun. 44 2008 5915 5917
17. 2+ Mater. Technol. 26 2011 168 172
18. N. Shao, Y. Zhang, S. Cheung, R. Yang, W. Chan, T. Mo, K. Li, and F. Liu Copper ion-selective fluorescent sensor based on the inner filter effect using a spiropyran derivative Anal. Chem. 77 2005 7294 7303
19. 2+-Selective ratiometric 'off-on' sensor based on the rhodamine derivative bearing pyrene group Org. Lett. 11 2009 4442 4445
20. C. Lin, and J. Yang Fluorescence response of TICT-active aminostilbenes to copper(II) ions: redox reaction vs ion recognition Res. Chem. Intermed. 39 2013 19 32
21. 2+-selective fluorescent chemosensor with different charge transfer processses Inorg. Chem. 51 2012 12444 12449
22. 2+ in aqueous solution and living cells Dalton Trans. 42 2013 1827 1833
23. 2+ selective colorimetric and fluorescent sensor via unique radical formation Chem. Commun. 49 2013 176 178
24. X. Lou, Y. Zhang, S. Li, D. Ou, Z. Wan, J. Qin, and Z. Li A new polyfluorene bearing pyridine moieties: a sensitive fluorescent chemosensor for metal ions and cyanide Polym. Chem. 3 2012 1446 1452
25. Q. Zeng, P. Cai, Z. Li, J. Qin, and B. Tang An imidazole-functionalized polyacetylene: convenient synthesis and selective chemosensor for metal ions and cyanide Chem. Commun. 44 2008 1094 1096
26. 2+ sensors based on indoline-benzothiadiazole derivatives via formation of radical cations ACS Appl. Mater. Inter. 5 2013 12215 12220
27. 2- in physiological conditions and in live cells Inorg. Chem. 52 2013 743 752
28. M.R. Ajayakumar, D. Asthana, and P. Mukhopadhyay Core-modified naphthalenediimides generate persistent radical anion and cation: new panchromatic NIR probes Org. Lett. 14 2012 4822 4825
29. N. Boens, V. Leen, and W. Dehaen Fluorescent indicators based on BODIPY Chem. Soc. Rev. 41 2012 1130 1172
30. Y. Chen, J. Zhao, H. Guo, and L. Xie Geometry relaxation-induced large stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes J. Org. Chem. 77 2012 2192 2206
31. T. Harada, K. Sano, K. Sato, R. Watanabe, Z. Yu, H. Hanaoka, T. Nakajima, P.L. Choyke, M. Ptaszek, and H. Kobayashi Activatable organic near-infrared fluorescent probes based on a bacteriochlorin platform: synthesis and multicolor in vivo imaging with a single excitation Bioconjug. Chem. 25 2014 362 369
32. J.O. Escobedo, O. Rusin, S. Lim, and R.M. Strongin NIR dyes for bioimaging applications Curr. Opin. Chem. Biol. 14 2010 64 70
33. R. Wang, F. Yu, L. Chen, H. Chen, L. Wang, and W. Zhang A highly selective turn-on near-infrared fluorescent probe for hydrogen sulfide detection and imaging in living cells Chem. Commun. 48 2012 11757 11759
34. P. Li, X. Duan, Z. Chen, Y. Liu, T. Xie, L. Fang, X. Li, M. Yin, and B. Tang A near-infrared fluorescent probe for detecting copper(II) with high selectivity and sensitivity and its biological imaging applications Chem. Commun. 47 2011 7755 7757
35. + in live cells Chem. Commun. 48 2012 6247 6249
36. X. Lu, W. Zhu, Y. Xie, X. Li, Y. Gao, F. Li, and H. Tian Near-IR core-substituted naphthalenediimide fluorescent chemosensors for zinc ions: ligand effects on PET and ICT channels Chem. Eur. J. 16 2010 8355 8364
37. Q. Li, M. Peng, H. Li, C. Zhong, L. Zhang, X. Cheng, X. Peng, Q. Wang, J. Qin, Z. Li, and A. New Turn-on naphthalenedimide-based chemosensor for mercury ions with high selectivity: the successful utilization of the mechanism of twisted intramolecular charge transfer, near-IR fluorescence and cell images Org. Lett. 14 2012 2094 2097
38. Q. Li, Y. Guo, and S. Shao A BODIPY based fluorescent chemosensor for Cu(II) ions and homocysteine/cysteine Sens. Actuators B 171-172 2012 872 877
39. 2+ sensors based on indoline-benzothiadiazole derivatives via formation of radical cations ACS Appl. Mater. Interfaces 5 2013 12215 12220
40. 2+-Responsive bimodal (optical/MRI) contrast agent for cellular imaging Org. Lett. 15 2013 4702 4705
41. N.E. Good, G.D. Winget, W. Winter, T.N. Connolly, S. Izawa, and R.M.M. Singh Hydrogen ion buffers for biological research Biochemistry 5 1966 467 477
42. C.A. Vega, and R.G. Bates Buffers for the physiological pH range: thermodynamic constants of four substituted aminoethanesulfonic acids from 5 to 50 degree C Anal. Chem. 48 1976 1293 1296
43. B. Biswal, and B. Bag Preferences of rhodamine coupled (aminoalkyl)-piperazine probes towards Hg(II) ion and their FRET mediated signaling Org. Biomol. Chem. 11 2013 4975 4992
44. X. Xu, J. Li, Q. Li, J. Huang, Y. Dong, Y. Hong, J. Yan, J. Qin, Z. Li, and B. Tang A Strategy for dramatically enhancing the selectivity of molecules showing aggregation-induced emission towards biomacromolecules with the aid of graphene oxide Chem. Eur. J. 18 2012 7278 7286