A fluorescent turn-on probe based on benzo [E] indolium for cyanide ion in water with high selectivity

Journal of Fluorescence

Volumn 23, Issue 6, 2013, Pages 1255-1261

  Sun, Yue ^a   Fan, Shanwei ^a   Zhao, Dong ^a   Duan, Lian ^a   Li, Ruifeng ^a  

^a TAIYUAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

benzo e indolium; Chemosensor; Cyanide sensing; Fluorescent turn on

Indexed keywords

BENZO [E] INDOLIUM; CHEMOSENSOR; CYANIDE-SENSING; DETECTION LIMITS; FLUORESCENCE ENHANCEMENT; FLUORESCENT TURN-ON; HIGH SELECTIVITY; NUCLEOPHILIC ATTACK;

CYANIDES; FLUORESCENCE;

PROBES;

BENZO(E)INDOLIUM; CYANIDE; FLUORESCENT DYE; INDOLE DERIVATIVE; ION; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; PH; SPECTROFLUOROMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

CYANIDES; FLUORESCENCE; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; INDOLES; IONS; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 84886788229     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-013-1258-y     Document Type: Article

References (42)

1. Kulig KW (1991) Cyanide toxicity. U.S. Department of Health and Human Services, Atlanta
2. Sidell F, Takafuji ET, Franz DR (1997) Medical aspects of chemical and biological warfare. TMM Publications, Washington, DC, p 271, Chapter 10
3. Baird C, Cann M (2005) Environmental chemistry. Freeman, New York
4. Miller GC, Pritsos CA (2001) Cyanide: Soc., Ind. Econ. Aspects, Proc. Symp. Annu. Meet. TMS: 73-81
5. Xu Z, Chen X, Kim HN, Yoon J (2010) Sensors for the optical detection of cyanide ion. Chem Soc Rev 39:127-137
6. Kim Y, Hong J (2002) Ion pair recognition by Zn-porphyrin/crown ether conjugates: Visible sensing of sodium cyanide. Chem Commun 512-513
7. Chow CF, Lam MHW, Wong WY (2004) A heterobimetallic Ruthenium (II) - Copper (II) donor-acceptor complex as a chemodosimetric ensemble for selective cyanide detection. Inorg Chem 43:8387-8393
8. Lee JH, Jeong AR, Shin I, Kim H, Hong J (2010) Fluorescence turn-on sensor for cyanide based on a Cobalt (II)-coumarinylsalen complex. Org Lett 12:764-767
9. Chung S, Nam S, Lim J, Park S, Yoon J (2009) A highly selective cyanide sensing in water via fluorescence change and its application to in vivo imaging. Chem Commun 2866-2868
10. Chem X, Nam S, Kim G, Song N, Jeong Y, Shin I, Kim SK, Kim J, Park S, Yoon J (2010) A near-infrared fluorescent sensor for detection of cyanide in aqueous solution and its application for bioimaging. Chem Commun 46:8953-8955
11. 2+-specific fluorescent molecular probe for the selective detection of endogenous cyanide in biorelevant samples. Chem Commun 46:6069-6071
12. Jung HS, Han JH, Kim ZH, Kang C, Kim JS (2011) Coumarin-Cu (II) ensemble-based cyanide sensing chemodosimeter. Org Lett 13:5056-5059
13. - specific turn-on phosphorescent probe with probable application for enzymatic assay and as an imaging reagent. Chem Commun 49:255-257
14. Ekmekci Z, Yilmaz DM, Akkaya EU (2008) A monostyryl-boradiazaindacene (BODIPY) derivative as colorimetric and fluorescent probe for cyanide ions. Org Lett 10:461-464
15. Peng L, Wang M, Zhang G, Zhang D, Zhu D (2009) A fluorescence turn-on detection of cyanide in aqueous solution based on the aggregation-induced emission. Org Lett 11:1943-1946
16. Jo J, Lee D, Am J (2009) Turn-on fluorescence detection of cyanide in water: Activation of latent fluorophores through remote hydrogen bonds that mimic peptide β-turn motif. Chem Soc 131:16283-16291
17. Kim S, Hong S, Yoo J, Kim S, Sessler JL, Lee CH (2009) Strapped calyx [4] pyrroles bearing a 1, 3-indanedione at a β-pyrrolic position: Chemodosimeters for the cyanide anion. Org Lett 11:3626-3629
18. Niu H, Jiang X, He J, Cheng J (2009) A highly selective and synthetically facile aqueous-phase cyanide probe. Tetrahedron Lett 50:6521-6524
19. Sun Y, Liu Y, Guo W (2009) Fluorescent and chromogenic probes bearing salicylaldehyde hydrazone functionality for cyanide detection in aqueous solution. Sens Actuators B 143:171-176
20. Park I, Jung Y, Lee K, Kim J (2010) Photoswitching and sensor applications of a spiropyran-polythiophene conjugate. Chem Commun 46:2859-2861
21. Park S, Kim H (2010) Highly activated Michael acceptor by an intramolecular hydrogen bond as a fluorescence turn-on probe for cyanide. Chem Commun 46:9197-9199
22. Yu H, Fu M, Xiao Y (2010) Switching off FRET by analyte-induced decomposition of squaraine energy acceptor: A concept to transform 'turn off' chemodosimeter into ratiometric sensors. Phys Chem Chem Phys 12:7386-7391
23. Yu H, Zhao Q, Jiang Z, Qin J, Li Z (2010) A ratiometric fluorescent probe for cyanide: Convenient synthesis and the proposed mechanism. Sens Actuators B 148:110-116
24. Lv X, Liu J, Liu Y, Zhao Y, Sun Y, Wang P, Guo W (2011) Ratiometric fluorescence detection of cyanide based on a hybrid coumarin-hemicyanine dye: the large emission shift and the high selectivity. Chem Commun 47:12843-12845
25. Yuan L, Lin W, Yang Y, Song J, Wang J (2011) Rational design of a highly reactive ratiometric fluorescent probe for cyanide. Org Lett 13:3730-3733
26. Kim H, Ko K, Lee J, Lee J, Kim J (2011) KCN sensor: unique chromogenic and 'turn-on' fluorescent chemodosimeter: rapid response and high selectivity. Chem Commun 47:2886-2888
27. Shiraishi Y, Sumiya S, Hirai T (2011) Highly sensitive cyanide anion detection with a coumarin-spiropyran conjugate as a fluorescent receptor. Chem Commun 47:4953-4955
28. Sumiya S, Doi T, Shiraishi Y, Hiral T (2012) Colorimetric sensing of cyanide anion in aqueous media with a fluoresceinespiropyran conjugate. Tetrahedron 68:690-696
29. Parka S, Hong K, Hong J, Kim H (2012) Azo dye-based latent colorimetric chemodosimeter for the selective detection of cyanides in aqueous buffer. Sens Actuators B 174:140-144
30. Huang X, Gu X, Zhang G, Zhang D (2012) A highly selective fluorescence turn-on detection of cyanide based on the aggregation of tetraphenylethylene molecules induced by chemical reaction. Chem Commun 48:12195-12197
31. Pati PB, Zade SSEuro (2012) Selective colorimetric and "Turn-on" fluorimetric detection of cyanide using a chemodosimeter comprising salicylaldehyde and triphenylamine groups. Euro J Org Chem 6555-6561
32. Lee C, Yoon H, Shim J, Jang W (2012) A boradiazaindacene-based turn-on fluorescent probe for cyanide detection in aqueous media. Chem Eur J 18:4513-4516
33. Ros-Lis JV, Martinez-Manez R, Soto J (2005) Subphthalocyanines as fluoro-chromogenic probes for anions and their application to the highly selective and sensitive cyanide detection. Chem Commun 5260-5262
34. Jamkratoke M, Ruangpornvisuti V, Tumcharern G, Tuntulani T, Tomapatanaget B (2009) A-D-A sensors based on naphthoimidazoledione and boronic acid as turn-on cyanide probes in water. J Org Chem 74:3919-3922
35. Feng L, Wang Y, Liang F, Liu W, Wang X, Diao H (2012) A specific sensing ensemble for cyanide ion in aqueous solution. Sens Actuators B 168:365-369
36. Lee K, Kim H, Kim G, Shin I, Hong J (2008) Fluorescent chemodosimeter for selective detection of cyanide in water. Org Lett 10:49-51
37. Sun Y, Fan S, Duan L, Li R (2013) A ratiometric fluorescent probe based on benzo [e] indolium for cyanide ion in water. Sens Actuators B 185:638-643
38. Tomasulo M, Raymo FM (2005) Colorimetric detection of cyanide with a chromogenic oxazine. Org Lett 7:4633-4636
39. Tomasulo M, Sortino S, White AJP, Raymo FM (2006) Chromogenic oxazines for cyanide detection. J Org Chem 71:744-753
40. Ren J, Zhu W, Tian H (2008) A highly sensitive and selective chemosensor for cyanide. talanta 75:760-764
41. Shiraishi Y, Adachi K, Itoh M, Hirai T (2009) Spiropyran as a selective, sensitive, and reproducible cyanide anion receptor. Org Lett 11:3482-3485
42. Chen Y, Zhu C, Yang Z, Chen J, He Y, Jiao Y, He W, Qiu L, Cen J, Guo Z (2013) A ratiometric fluorescent probe for rapid detection of hydrogen sulfide in mitochondria. Angew Chem Int Ed 52:1688-1691