Citation: Zhang Yuan, Fang Yuan, Xu Nai-Zhang, Zhang Ming-Qun, Wu Guan-Zhi, Yao Cheng. A colorimetric and ratiometric fluorescent chemosensor based on furan-pyrene for selective and sensitive sensing Al³⁺[J]. Chinese Chemical Letters, ;2016, 27(11): 1673-1678. doi: 10.1016/j.cclet.2016.04.011 shu

A colorimetric and ratiometric fluorescent chemosensor based on furan-pyrene for selective and sensitive sensing Al³⁺

a.
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China
b.
State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China
c.
College of Overseas Education, Nanjing Tech University, Nanjing 211816, China

Corresponding author: Yao Cheng, yaocheng@njtech.edu.cn; yaochengnjut@126.com
Received Date: 8 March 2016
Revised Date: 11 April 2016
Accepted Date: 14 April 2016
Available Online: 21 November 2016

Figures(9)

A new pyrene derivative BF bearing a furan group was synthesized via a one-step reaction as a colorimetric and ratiometric chemosensor for Al³⁺in ethanol-H₂O (9:1, v/v, pH 7.2, HEPES buffer) solution.This chemosensor could selectively recognize Al³⁺ in the presence of other competing ions.Low limit of detection (LOD) and high association constant revealed its superior sensitivity and binding affinity toward Al³⁺.Besides, the probe BF performed perfectly in a reversibility test using EDTA.The mechanism of the interaction has been confirmed by ¹H NMR titration.Importantly, chemosensor BF has also been utilized to detect Al³⁺ on test paper strips, which showed its potential for practical applications.
- Pyrene,
- Al³⁺,
- Colorimetric,
- Ratiometric,
- Chemosensor,
- Application
1. [1]
  Prodi L., Montalti M., Zaccheroni N.. Characterization of 5-chloro-8-methoxyquinoline appended diaza-18-crown-6 as a chemosensor for cadmium[J]. Tetrahedron Lett., 2001,42:2941-2944. doi: 10.1016/S0040-4039(01)00330-6
2. [2]
  Rurack K., Kollmannsberger M., Resch-Genger U., Daub J.. A selective and sensitive fluoroionophore for Hg^Ⅱ, Ag^Ⅰ, and Cu^Ⅱ with virtually decoupled fluorophore and receptor units[J]. J. Am. Chem. Soc., 2000,122:968-969. doi: 10.1021/ja992630a
3. [3]
  Butler O.T., Cook J.M., Davidson C.M., Harrington C.F., Miles D.L.. Atomic spectrometry update. Environmental analysis[J]. J. Anal. At. Spectrom., 2009,24:131-177. doi: 10.1039/b821579k
4. [4]
  Li Y.F., Chen C.Y., Li B.. Elimination efficiency of different reagents for the memory effect of mercury using ICP-MS[J]. J. Anal. Atomic Spectrom., 2006,21:94-96. doi: 10.1039/B511367A
5. [5]
  Ueno T., Nagano T.. Fluorescent probes for sensing and imaging[J]. Nat. Meth., 2011,8:642-645. doi: 10.1038/nmeth.1663
6. [6]
  Robinson G.H.. Aluminum[J]. Chem. Eng. News, 2003,8154.
7. [7]
  Exley C.. Has edited a special issue devoted to 'Aluminium: Lithosphere to Biosphere (and Back)'[J]. J. Inorg. Biochem., 2005,99:1747-1920. doi: 10.1016/j.jinorgbio.2005.07.004
8. [8]
  Barceló J., Poschenrieder C.. Fast root growth responses, root exudates, and internal detoxification as clues to the mechanisms of aluminium toxicity and resistance: a review[J]. Environ. Exp. Bot., 2002,48:75-92. doi: 10.1016/S0098-8472(02)00013-8
9. [9]
  Valeur B., Leray I.. Design principles of fluorescent molecular sensors for cation recognition[J]. Coord. Chem. Rev., 2000,205:3-40. doi: 10.1016/S0010-8545(00)00246-0
10. [10]
  Krejpcio Z., Wojciak R.. The influence of Al³⁺ ions on pepsin and trypsin activity in vitro[J]. Polish J. Environ. Studies, 2002,11:251-254.
11. [11]
  Perl D.P., Gajdusek D.C., Garruto R.M., Yanagihara R.T., Gibbs C.J.. Intraneuronal aluminum accumulation in amyotrophic lateral sclerosis and Parkinsonismdementia of Guam[J]. Science, 1982,217:1053-1055. doi: 10.1126/science.7112111
12. [12]
  Perl D.P., Brody A.R.. Alzheimer's disease: X-ray spectrometric evidence of aluminum accumulation in neurofibrillary tangle-bearing neurons[J]. Science, 1980,208:297-299. doi: 10.1126/science.7367858
13. [13]
  Soroka K., Vithanage R.S., Phillips D.A., Walker B., Dasgupta P.K.. Fluorescence properties of metal complexes of 8-hydroxyquinoline-5-sulfonic acid and chromatographic applications[J]. Anal. Chem., 1987,59:629-636. doi: 10.1021/ac00131a019
14. [14]
  Al-Kindy S.M.Z., Suliman F.E.O., Pillay A.E.. Fluorimetric determination of aluminium using sequential injection analysis (SIA): state of our art and future developments[J]. Instr. Sci. Technol., 2006,34:619-633. doi: 10.1080/10739140600963830
15. [15]
  Han T.Y., Feng X., Tong B.. A novel "turn-on" fluorescent chemosensor for the selective detection of Al³⁺ based on aggregation-induced emission[J]. Chem. Commun., 2012,48:416-418. doi: 10.1039/C1CC15681K
16. [16]
  Shi X.Y., Wang H., Han T.Y.. A highly sensitive, single selective, real-time and "turn-on" fluorescent sensor for Al³⁺ detection in aqueous media[J]. J. Mater. Chem., 2012,22:19296-19302. doi: 10.1039/c2jm33393g
17. [17]
  Ding W.H., Cao W., Zheng X.J.. A highly selective fluorescent chemosensor for Al^Ⅲ ion and fluorescent species formed in the solution[J]. Inorg. Chem., 2013,52:7320-7322. doi: 10.1021/ic401028u
18. [18]
  Lu Y., Huang S.S., Liu Y.Y.. Highly selective and sensitive fluorescent turn-on chemosensor for Al³⁺ based on a novel photoinduced electron transfer approach[J]. Org. Lett., 2011,13:5274-5277. doi: 10.1021/ol202054v
19. [19]
  Ren J.L., Zhang J., Luo J.Q., Pei X.K., Jiang Z.X.. Improved fluorimetric determination of dissolved aluminium by micelle-enhanced lumogallion complex in natural waters[J]. Analyst, 2001,126:698-702. doi: 10.1039/b007593k
20. [20]
  Ng S.M., Narayanaswamy R.. Fluorescence sensor using a molecularly imprinted polymer as a recognition receptor for the detection of aluminium ions in aqueous media[J]. Anal. Bioanal. Chem., 2006,386:1235-1244. doi: 10.1007/s00216-006-0736-3
21. [21]
  Wang Y.W., Yu M.X., Yu Y.H.. A colorimetric and fluorescent turn-on chemosensor for Al³⁺ and its application in bioimaging[J]. Tetrahedron Lett., 2009,50:6169-6172. doi: 10.1016/j.tetlet.2009.08.078
22. [22]
  J.B. Birks, Photophysics of Aromatic Molecules, Wiley Interscience, London, 1970.
23. [23]
  Lee Y.O., Lee J.Y., Quang D.T., Lee M.H., Kim J.S.. Pyrene-coumarin based calix fluorophore emitting exciplex[J]. Bull. Kor. Chem. Soc., 2006,271469. doi: 10.5012/bkcs.2006.27.9.1469
24. [24]
  Park H.R., Oh C.H., Lee H.C.. Quenching of ofloxacin and flumequine fluorescence by divalent transition metal cations[J]. Bull. Korean Chem. Soc., 2006,27:2002-2010. doi: 10.5012/bkcs.2006.27.12.2002
25. [25]
  Sun X., Wang Y.W., Peng Y.. A selective and ratiometric bifunctional fluorescent probe for Al³⁺ ion and proton[J]. Org. Lett., 2012,14:3420-3423. doi: 10.1021/ol301390g
26. [26]
  Liu J.W., Lu Y.. Rational design of "turn-on" allosteric DNAzyme catalytic beacons for aqueous mercury ions with ultrahigh sensitivity and selectivity[J]. Angew. Chem., 2007,119:7731-7734. doi: 10.1002/(ISSN)1521-3757
27. [27]
  Lee Y.J., Lim C., Suh H., Song E.J., Kim C.. A multifunctional sensor: chromogenic sensing for Mn²⁺ and fluorescent sensing for Zn²⁺ and Al³⁺[J]. Sensors Actuat. B: Chem., 2014,201:535-544. doi: 10.1016/j.snb.2014.05.035
28. [28]
  Liu Y.W., Chen C.H., Wu A.T.. A turn-on and reversible fluorescence sensor for Al³⁺ ion[J]. Analyst, 2012,137:5201-5203. doi: 10.1039/c2an35854a
29. [29]
  Patil R., Moirangthem A., Butcher R.. Al³⁺ selective colorimetric and fluorescent red shifting chemosensor: application in living cell imaging[J]. Dalton Trans., 2014,43:2895-2899. doi: 10.1039/C3DT52770K
30. [30]
  Kaur K., Bhardwaj V.K., Kaur N., Singh N.. Imine linked fluorescent chemosensor for Al³⁺ and resultant complex as a chemosensor for HSO4 anion[J]. Inorg. Chem. Commun., 2012,18:79-82. doi: 10.1016/j.inoche.2012.01.018
31. [31]
  Kaur K., Bhardwaj V.K., Kaur N., Singh N.. Fluorescent chemosensor for Al³⁺ and resultant complex as a chemosensor for perchlorate anion: first molecular security keypad lock based on Al³⁺ and ClO₄-inputs[J]. Inorg. Chem. Commun., 2012,26:31-36. doi: 10.1016/j.inoche.2012.09.008
32. [32]
  Mahapatra A.K., Ali S.S., Maiti K.. Aminomethylpyrene-based imino-phenols as primary fluorescence switch-on sensors for Al³⁺ in solution and in Vero cells and their complexes as secondary recognition ensembles toward pyrophosphate[J]. RSC Adv., 2015,5:81203-81211. doi: 10.1039/C5RA16641A
33. [33]
  Gupta V.K., Mergu N., Singh A.K.. Rhodamine-derived highly sensitive and selective colorimetric and off-on optical chemosensors for Cr³⁺[J]. Sensors Actuat. B: Chem., 2015,220:420-432. doi: 10.1016/j.snb.2015.05.075
34. [34]
  Fu Y., Jiang X.J., Zhu Y.Y.. A new fluorescent probe for Al³⁺ based on rhodamine 6G and its application to bioimaging[J]. Dalton Trans., 2014,43:12624-12632. doi: 10.1039/C4DT01453G
35. [35]
  Ding W.H., Cao W., Zheng X.J.. A tetrazole-based fluorescence "turn-on" sensor for Al (iii) and Zn (ii) ions and its application in bioimaging[J]. Dalton Trans., 2014,43:6429-6435. doi: 10.1039/c4dt00009a
36. [36]
  Cao W., Zheng X.J., Sun J.P.. A highly selective chemosensor for Al (Ⅲ) and Zn (Ⅱ) and its coordination with metal ions[J]. Inorg. Chem., 2014,53:3012-3021. doi: 10.1021/ic402811x
37. [37]
  Long Y., Zhou J., Yang M.P., Yang B.Q.. A selective and sensitive off-on probe for palladium and its application for living cell imaging[J]. Chin. Chem. Lett., 2016,27:205-210. doi: 10.1016/j.cclet.2015.09.003
38. [38]
  Benesi H.A., Hildebrand J.H.. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons[J]. J. Am. Chem. Soc., 1949,71:2703-2707. doi: 10.1021/ja01176a030
39. [39]
  Yang X.B., Yang B.X., Ge J.F.. Benzo[a]phenoxazinium-based red-emitting chemosensor for zinc ions in biological media[J]. Org. Lett., 2011,13:2710-2713. doi: 10.1021/ol2008022
40. [40]
  Zhu M., Yuan M.J., Liu X.F.. Visible near-infrared chemosensor for mercury ion[J]. Org. Lett., 2008,10:1481-1484. doi: 10.1021/ol800197t
41. [41]
  Jiang X.D., Yu H.F., Zhao J.L.. A colorimetric chemosensor based on new water-soluble PODIPY dye for Hg²⁺ detection[J]. Chin. Chem. Lett., 2015,26:1241-1245. doi: 10.1016/j.cclet.2015.07.002
1. [1]
  Rongxin Zhu , Shengsheng Yu , Xuanzong Yang , Ruyu Zhu , Hui Liu , Kaikai Niu , Lingbao Xing . Construction of pyrene-based hydrogen-bonded organic frameworks as photocatalysts for photooxidation of styrene in water. Chinese Chemical Letters, 2024, 35(10): 109539-. doi: 10.1016/j.cclet.2024.109539
2. [2]
  Jia Fu , Shilong Zhang , Lirong Liang , Chunyu Du , Zhenqiang Ye , Guangming Chen . PEDOT-based thermoelectric composites: Preparation, mechanism and applications. Chinese Chemical Letters, 2024, 35(9): 109804-. doi: 10.1016/j.cclet.2024.109804
3. [3]
  Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
4. [4]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
5. [5]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
6. [6]
  Tiantian Zheng , Huiyi Wang , Huimin Li , Xuanhe Liu , Hong Shang . Anti-Counterfeiting National Salvation Chronicle of 006. University Chemistry, 2024, 39(9): 254-258. doi: 10.3866/PKU.DXHX202307032
7. [7]
  Miaomiao He , Zhiqing Ge , Qiang Zhou , Jiaqing He , Hong Gong , Lingling Li , Pingping Zhu , Wei Shao . Exploring the Fascinating Realm of Quantum Dots. University Chemistry, 2024, 39(6): 231-237. doi: 10.3866/PKU.DXHX202310040
8. [8]
  Gengchen Guo , Tianyu Zhao , Ruichang Sun , Mingzhe Song , Hongyu Liu , Sen Wang , Jingwen Li , Jingbin Zeng . Au-Fe₃O₄ dumbbell-like nanoparticles based lateral flow immunoassay for colorimetric and photothermal dual-mode detection of SARS-CoV-2 spike protein. Chinese Chemical Letters, 2024, 35(6): 109198-. doi: 10.1016/j.cclet.2023.109198
9. [9]
  Xinlong Zheng , Zhongyun Shao , Jiaxin Lin , Qizhi Gao , Zongxian Ma , Yiming Song , Zhen Chen , Xiaodong Shi , Jing Li , Weifeng Liu , Xinlong Tian , Yuhao Liu . Recent advances of CuSbS₂ and CuPbSbS₃ as photocatalyst in the application of photocatalytic hydrogen evolution and degradation. Chinese Chemical Letters, 2025, 36(3): 110533-. doi: 10.1016/j.cclet.2024.110533
10. [10]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
11. [11]
  Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860
12. [12]
  Yijian Zhao , Jvzhe Li , Yunyi Shi , Jie Hu , Meiyi Liu , Yao Shen , Xinglin Hou , Qiuyue Wang , Qi Wang , Zhiyi Yao . A label-free and ratiometric fluorescent sensor based on porphyrin-metal-organic frameworks for sensitive detection of ochratoxin A in cereal. Chinese Chemical Letters, 2025, 36(4): 110132-. doi: 10.1016/j.cclet.2024.110132
13. [13]
  Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
14. [14]
  Guorong Li , Yijing Wu , Chao Zhong , Yixin Yang , Zian Lin . Predesigned covalent organic framework with sulfur coordination: Anchoring Au nanoparticles for sensitive colorimetric detection of Hg(Ⅱ). Chinese Chemical Letters, 2024, 35(5): 108904-. doi: 10.1016/j.cclet.2023.108904
15. [15]
  Caixia Zhu , Qing Hong , Kaiyuan Wang , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Single nanozyme-based colorimetric biosensor for dopamine with enhanced selectivity via reactivity of oxidation intermediates. Chinese Chemical Letters, 2024, 35(10): 109560-. doi: 10.1016/j.cclet.2024.109560
16. [16]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
17. [17]
  Simin Wei , Yaqing Yang , Junjie Li , Jialin Wang , Jinlu Tang , Ningning Wang , Zhaohui Li . The Mn/Yb/Er triple-doped CeO₂ nanozyme with enhanced oxidase-like activity for highly sensitive ratiometric detection of nitrite. Chinese Chemical Letters, 2024, 35(6): 109114-. doi: 10.1016/j.cclet.2023.109114
18. [18]
  Yuxin Wang , Zhengxuan Song , Yutao Liu , Yang Chen , Jinping Li , Libo Li , Jia Yao . Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity. Chinese Chemical Letters, 2024, 35(6): 108779-. doi: 10.1016/j.cclet.2023.108779
19. [19]
  Zhaoru Chen , Xiaoxu Liu , Haonan Chen , Jialong Li , Xiaofeng Wang , Jianfeng Zhu . Application of epoxy resin in cultural relics protection. Chinese Chemical Letters, 2024, 35(4): 109194-. doi: 10.1016/j.cclet.2023.109194
20. [20]
  Binhan Zhao , Zheng Li , Lan Zheng , Zhichao Ye , Yuyang Yuan , Shanshan Zhang , Bo Liang , Tianyu Li . Recent progress in the biomedical application of PEDOT:PSS hydrogels. Chinese Chemical Letters, 2024, 35(10): 109810-. doi: 10.1016/j.cclet.2024.109810

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(689)
HTML views(1)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

A colorimetric and ratiometric fluorescent chemosensor based on furan-pyrene for selective and sensitive sensing Al3+

Metrics

通讯作者: 陈斌, bchen63@163.com

A colorimetric and ratiometric fluorescent chemosensor based on furan-pyrene for selective and sensitive sensing Al³⁺