Citation: LIN Shengsheng, HE Qingyun, ZHOU Jiamin, ZHAO Mingpeng, FENG Zongcai, YU Biao, SONG Xiumei. Colorimetric Sensors for Anion Recognition Based on Benzeneazophenol[J]. Chinese Journal of Applied Chemistry, ;2019, 36(12): 1447-1455. doi: 10.11944/j.issn.1000-0518.2019.12.190084 shu

Colorimetric Sensors for Anion Recognition Based on Benzeneazophenol

a.
Institute for Advanced Materials, Lingnan Normal University, Zhanjiang 524048, China
b.
School of Chemistry and Chemical Engineering, Lingnan Normal University, Zhanjiang 524048, China

Corresponding author: SONG Xiumei, sxmfn@163.com
Received Date: 1 April 2019
Revised Date: 10 June 2019
Accepted Date: 11 July 2019

Fund Project: the Science and Technology Planning Project of Zhanjiang 2015A020203the National Natural Science Foundation of China 21805125the Innovation and Entrepreneurship Training Program for College Students 201810579701Supported by the National Natural Science Foundation of China(No.21805125), the Science and Technology Planning Project of Zhanjiang(No.2015A020203), and the Innovation and Entrepreneurship Training Program for College Students(No.201810579701)

Figures(8)

Three colorimetric sensors S1, S2 and S3 based on azobenzene containing different numbers of active phenolic hydroxyl groups have been designed and synthesized. The sensors in CH₃CN exhibit high sensitivity toward F^-, H₂PO₄^- and AcO^-. The detection limit of S1, S2 and S3 was determined to be 1.25×10^-7~3.62×10^-7 mol/L for F^-. The sensitivity of sensors S1, S2 and S3 for anions were affected by the configuration, charge density and basicity of anions. ¹H NMR titration has been performed to study reaction mechanism, which was considered to be direct consequence of hydrogen-bonding between the phenolic group of sensor and anion.
- azobenzene,
- colorimetric recognition,
- anion,
- chemosensors,
- phenolic hydroxyl group
1. [1]
  Gale P A. Anion Receptor Chemistry[J]. Chem Comun, 2011,47(1):82-86. doi: 10.1039/C0CC00656D
2. [2]
  Sun H, Dong X, Liu S. Excellent BODIPY Dye Containing Dimesitylboryl Groups as Pet Based Fluorescent Probes for Fluoride[J]. J Phys Chem C, 2011,115(40):19947-19954. doi: 10.1021/jp206396v
3. [3]
  Li S, Zhang C, Huang S. Highly Selective Colorimetric and Fluorescent Sensors for the Fluoride Anion Based on Imidazo[4, 5-f]-1, 10-phenanthroline Metal-Complexes[J]. RCS Adv, 2012,2:4215-4219.
4. [4]
  Yong X, Su M, Wan W. 2-Thiohydantoin Containing OH and NH Recognition Subunits:A Fluoride Ion Selective Colorimetric Sensor[J]. New J Chem, 2013,37(5):1591-1594. doi: 10.1039/c3nj41134f
5. [5]
  Li X G, Zhang D, Li J. Emission "Off-On" Effect from Curopium Complexes Triggered by AcO Anion:Synthesis, Characterization and Sensing Performance[J]. Spectrochim Acta, Part A, 2014,127:1-9. doi: 10.1016/j.saa.2014.02.042
6. [6]
  Khan S S, Riaz M. Determination of UV Active Inorganic Anions in Potable and High Salinity Water by Ion Pair Reversed Phase Liquid Chromatography[J]. Talanta, 2014,122:209-213. doi: 10.1016/j.talanta.2014.01.059
7. [7]
  Hu B B, Lu P, Wang Y G. A Highly Selective and Real-Time Ratiometric Fluorescent Chemosensor for Fluoride Anion Detection under Either Neutral or Basic Condition[J]. Sens Actuators, B, 2014,195:320-323. doi: 10.1016/j.snb.2014.01.058
8. [8]
  Guha S, Saha S. Fluoride Ion Sensing by an Anion-π Interaction[J]. J Am Chem Soc, 2010,132(50):17674-17677. doi: 10.1021/ja107382x
9. [9]
  Xu W, Liu S, Sun H. FRET-Based Probe for Fluoride Based on a Phosphorescent Rridium(Ⅲ) Complex Containing Triarylboron Groups[J]. J Mater Chem, 2011,21(21):7572-7581. doi: 10.1039/c1jm00071c
10. [10]
  Baker J L, Sudarsan N, Weinberg Z. Widespread Genetic Switches and Toxicity Resistance Proteins for Fluoride[J]. Science, 2012,335(6065):233-235. doi: 10.1126/science.1215063
11. [11]
  Aboubakr H, Brisset H, Siri O. Highly Specific and Reversible Fluoride Sensor Based on an Organic Semiconductor[J]. Anal Chem, 2013,85(20):9968-9974. doi: 10.1021/ac4027934
12. [12]
  Iniya M, Jeyanthi D, Krishnaveni K. A Bifunctional Chromogenic and Fluorogenic Probe for F^- and Al³⁺ Based on Azo-Benzimidazole Conjugate[J]. J Lumin, 2015,157:383-389. doi: 10.1016/j.jlumin.2014.09.018
13. [13]
  Padhan S K, Podh M B, Sahu P K. Optical Discrimination of Fluoride and Cyanide Ions by Coumarin-Salicylidene Based Chromofluorescent Probes in Organic and Aqueous Medium[J]. Sens Actuators, B, 2018,255:1376-1390. doi: 10.1016/j.snb.2017.08.133
14. [14]
  Li Z Y, Su H K, Tong H X. Calix [4] arene Containing Thiourea and Coumarin Functionality as Highly Selective Fluorescent and Colorimetric Chemosensor for Fluoride Ion[J]. Spectrochim Acta, Part A, 2018,200:307-312. doi: 10.1016/j.saa.2018.04.040
15. [15]
  Lin Q, Yang Q P, Sun B. A Highly Selective and Sensitive Fluorescence Turn-On Fluoride Ion Sensor[J]. RSC Adv, 2015,5:11786-11790. doi: 10.1039/C4RA09624J
16. [16]
  Kumar G G V, Kesavan M P, Sivaraman G. Colorimetric and NIR Fluorescence Receptors for F^- Ion Detection in Aqueous Condition and Its Live Cell Imaging[J]. Sens Actuators, B, 2018,255:3194-3206. doi: 10.1016/j.snb.2017.09.145
17. [17]
  Wang R, Ma Y S, Zhao J F. Novel Hydroxyl-Substituted Perylene-3, 4, 9, 10-Tetracarboxylic Acid Diimides for Selective Recognition of Fluoride[J]. Sens Actuators, B, 2018,260:719-726. doi: 10.1016/j.snb.2017.12.171
18. [18]
  Ashokkumar P, Ramakrishnan V T, Ramamurthy P. Fluorescence Spectroscopic Evidence for Hydrogen Bonding and Deprotonation Equilibrium Between Fluoride and a Thiourea Derivative[J]. Chem Eur J, 2010,44(16):13271-13277.
19. [19]
  Mahapatra A K, Karmakar P, Roy J. Colorimetric and Ratiometric Fluorescent Chemosensor for Fluoride Ions Based on Phenanthroimidazole(PI):Spectroscopic, NMR and Density Functional Studies[J]. RSC Adv, 2015,47(5):37935-37942.
20. [20]
  Wu Y C, You J Y, Jiang K. Colorimetric and Ratiometric Fluorescent Sensor for F^- Based on Benzimidazole-Naphthalene Conjugate:Reversible and Reusable Study & Design of Logic Gate Function[J]. Dyes Pigm, 2017,140:47-55. doi: 10.1016/j.dyepig.2017.01.025
21. [21]
  Wu Y C, Huo J P, Cao L. Design and Application of Tri-Benzimidazolyl Star-Shape Molecules as Fluorescent Chemosensors for the Fast-Response Detection of Fluoride Ion[J]. Sens Actuators, B, 2016,237:865-875. doi: 10.1016/j.snb.2016.07.028
22. [22]
  Singh H, Bhargava G, Kumar S. Microstructural (Self-assembly) and Optical Based Discrimination of Hg²⁺, CN^- and Hg(CN)₂ Ion-Pair; Hg²⁺ Promoted-ESIPT Assisted Guanylation of Thiourea[J]. Sens Actuators, B, 2018,272:43-52. doi: 10.1016/j.snb.2018.05.104
23. [23]
  Wang S X, Meng X M, Zhu M Z. A Naked-eye Rhodamine-Based Fluorescent Probe for Fe(Ⅲ) and Its Application in Living Cells[J]. Tetrahedron Lett, 2011,52(22):2840-2843. doi: 10.1016/j.tetlet.2011.03.104
24. [24]
  Bera R K, Raj C R. Naked Eye Sensing of Melamine Using Rationally Tailored Gold Nanoparticles:Hydrogen-Bonding and Charge-Transfer Recognition[J]. Analyst, 2011,136(8):1644-1648. doi: 10.1039/c0an00870b
25. [25]
  Bao Y, Liu B, Wang H. A "Naked Eye" and Ratiometric Fluorescent Chemosensor for Rapid Detection of F^- Based on Combination of Desilylation Reaction and Excited-State Proton Transfer[J]. Chem Commun, 2011,47(13):3957-3959. doi: 10.1039/c1cc00034a
26. [26]
  Zhou X, Yan W, Zhao T. Rhodamine Based Derivative and Its Zinc Complex:Synthesis and Recognition Behavior Toward Hg(Ⅱ)[J]. Tetrahedron, 2013,69(46):9535-9539. doi: 10.1016/j.tet.2013.09.049
27. [27]
  Kim K B, Kim H, Song E J. A Cap-Type Schiff Base Acting as a Fluorescence Sensor for Zinc(Ⅱ) and a Colorimetric Sensor for Iron(Ⅱ), Copper(Ⅱ), and Zinc(Ⅱ) in Aqueous Media[J]. Dalton Trans, 2013,42(47):16569-16577. doi: 10.1039/c3dt51916c
28. [28]
  Shyamaprosad G, Maity S, Das A K. Remarkable ESIPT Induced NIR Emission by a Selective Colorimetric Dibenzimidazolo Diimine Sensor for Acetate[J]. Tetrahedron Lett, 2013,54(38):5232-5235. doi: 10.1016/j.tetlet.2013.07.078
29. [29]
  Gong Y N, Lu T B. Fast Detection of Oxygen by the Naked Eye Using a Stable Metal-Organic Framework Containing Methyl Viologen Cations[J]. Chem Commun, 2013,49(70):7711-7713. doi: 10.1039/c3cc42268b
30. [30]
  Zhu J, Yang X, Zhang L. A Visible Multi-Digit DNA Keypad Lock Based on Split G-Quadruplex DNAzyme and Silver Microspheres[J]. Chem Commun, 2013,49(48):5459-5461. doi: 10.1039/c3cc42028k
31. [31]
  Pandurangan K, Kitchen J A, Gunnlaugsson T. Colorimetric Naked-eye' Sensing of Anions Using a Thiosemicarbazide Receptor:A Case Study of Recognition Through Hydrogen Bonding Versus Deprotonation[J]. Tetrahedron Lett, 2013,54(22):2770-2775. doi: 10.1016/j.tetlet.2013.02.107
32. [32]
  Vinithra G, Suganya S, Velmathi S. Naked Eye Sensing of Anions Using Thiourea Based Chemosensors with Real Time Application[J]. Tetrahedron Lett, 2013,54(41):5612-5615. doi: 10.1016/j.tetlet.2013.08.005
33. [33]
  Batista R M F, Oliveira E, Costa S P G. Cyanide and Fluoride Colorimetric Sensing by Novel Imidazo-Anthraquinones Functionalized with Indole and Carbazole[J]. Supramol Chem, 2014,26(2):71-80. doi: 10.1080/10610278.2013.824082
34. [34]
  Ding L, Wu M J, Li Y R. New Fluoro- and Chromogenic Chemosensors for the Dual-channel Detection of Hg²⁺ and F^-[J]. Tetrahedron Lett, 2014,55(34):4711-4715. doi: 10.1016/j.tetlet.2014.06.094
35. [35]
  Satheshkumar A, El-Mossalamy E H, Manivannan R. Anion Induced Azo-Hydrazone Tautomerism for the Selective Colorimetric Sensing of Fluoride Ion[J]. Spectrochim Acta, Part A, 2014,128:798-805. doi: 10.1016/j.saa.2014.02.200
36. [36]
  Parthiban C, Elango K P. Amino-Naphthoquinone and Its Metal Chelates for Selective Sensing of Fluoride Ions[J]. Sens Actuators, B, 2015,215:544-552. doi: 10.1016/j.snb.2015.03.105
37. [37]
  Liu X M, Li Y P, Zhang Y H. Ratiometric Fluorescence Detection of Fluoride Ion by Indole-Based Receptor[J]. Talanta, 2015,131:597-602. doi: 10.1016/j.talanta.2014.08.017
38. [38]
  Yang X F, Zheng L Y, Xie L J. Colorimetric and On-Off Fluorescent Chemosensor for Fluoride Ion Based on Diketopyrrolopyrrole[J]. Sens Actuators B, 2015,207:9-24. doi: 10.1016/j.snb.2014.10.095
39. [39]
  Choi Y W, Lee J J, You G R. Chromogenic Naked-Eye Detection of Copper Ion and Fluoride[J]. RSC Adv, 2015,5(105):86463-86472. doi: 10.1039/C5RA16301C
40. [40]
  Yeung M C L, Yam V W W. Luminescent Cation Sensors:From Host-Guest Chemistry, Supramolecular Chemistry to Reaction-Based Mechanisms[J]. Chem Soc Rev, 2015,44(13):4192-4202. doi: 10.1039/C4CS00391H
41. [41]
  Lee H, Lee S S. Thiaoxaaza-Macrocyclic Chromoionphores as Mercury(Ⅱ) Sensors:Synthesis and Color Modulation[J]. Org Lett, 2009,11(6):1393-1396. doi: 10.1021/ol900241p
42. [42]
  Suganya S, Velmathi S. Simple Azo-Based Salicylaldimine as Colorimetric and Fluorescent Probe for Detecting Anions in Semi-aqueous Medium[J]. J Mol Recognit, 2013,26(6):259-267. doi: 10.1002/jmr.2268
43. [43]
  Hamid K, Khatereh R. Naked-Eye Detection of Inorganic Fluoride in Aqueous Media Using a New Azo-Azomethine Colorimetric Receptor Enhanced by Electron Withdrawing Groups[J]. RSC Adv, 2014,4(2):1032-1038. doi: 10.1039/C3RA42709A
44. [44]
  Udhayakumari D, Velmathi S. Azo Linked Thiourea Based Effective Dual Sensor and Its Real Samples Application in Aqueous Medium[J]. Sens Actuators, B, 2015,209:462-469. doi: 10.1016/j.snb.2014.11.139
45. [45]
  Simon D, Kannapiran R K. A Symmetrical Luminol Based Azo Derivative for Trimodal Ratiometric Hg²⁺ Sensing and Its Application to Bioimaging in Living Cells[J]. J Photochem Photobiol A, 2018,364:773-786. doi: 10.1016/j.jphotochem.2018.07.013
46. [46]
  Lee K H, Lee H Y, Lee D H. Fluoride-Selective Chromogenic Sensors Based on Azophenol[J]. Terahedron Lett, 2001,42(32):5447-5449. doi: 10.1016/S0040-4039(01)01011-5
47. [47]
  SONG Xiumei, FENG Zongcai, WANG Zhaoyang. Synthesis, Characterization and Photochromic Properties of D-π-A Azobenzene Derivatives[J]. J Funct Mater, 2015,46(9):09114-09119.
48. [48]
  SONG Xiumei, FENG Zongcai, WANG Yuechuan. Synthesis and Photoisomerization of Film Containing 2, 4, 2'-Trihydroxyazobenzene[J]. Polym Mater Sci Eng, 2014,30(6):38-41.
49. [49]
  Niu H, Shu Q H, Jin S H. A Simple Ratiometric and Colorimetric Chemosensor for the Selective Detection of Fluoride in DMSO Buffered Solution[J]. Spectrochim Acta, Part A, 2016,153:194-198. doi: 10.1016/j.saa.2015.08.030
50. [50]
  Sarkar A, Bhattacharyya S, Mukherjee A. Colorimetric Detection of Fluoride Ions by Anthraimidazoledione Based Sensors in the Presence of Cu(Ⅱ) Ions[J]. Dalton Trans, 2016,45:1166-1175. doi: 10.1039/C5DT03209A
51. [51]
  Gupta N, Singhal D, Singh A K. Highly Selective Colorimetric and Reversible Fluorometric Turn-Off Sensors Based on the Pyrimidine Derivative:Mimicking Logic Gate Operation and Potential Applications[J]. New J Chem, 2016,40:641-650. doi: 10.1039/C5NJ02118A
1. [1]
  Qiaojia GUO , Junkai CAI , Chunying DUAN . Effects of anions on the structural regulation of Zn-salen-modified metal-organic cage. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2203-2211. doi: 10.11862/CJIC.20240209
2. [2]
  Jiarong Feng , Yejie Duan , Chu Chu , Dezhen Xie , Qiu'e Cao , Peng Liu . Preparation and Application of a Streptomycin Molecularly Imprinted Electrochemical Sensor: A Suggested Comprehensive Analytical Chemical Experiment. University Chemistry, 2024, 39(8): 295-305. doi: 10.3866/PKU.DXHX202401016
3. [3]
  Meiqing Yang , Lu Wang , Haozi Lu , Yaocheng Yang , Song Liu . Recent Advances of Functional Nanomaterials for Screen-Printed Photoelectrochemical Biosensors. Acta Physico-Chimica Sinica, 2025, 41(2): 100018-. doi: 10.3866/PKU.WHXB202310046
4. [4]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
5. [5]
  Qiaoqiao BAI , Anqi ZHOU , Xiaowei LI , Tang LIU , Song LIU . Construction of pressure-temperature dual-functional flexible sensors and applications in biomedicine. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2259-2274. doi: 10.11862/CJIC.20240128
6. [6]
  Xingchao Zhao , Xiaoming Li , Ming Liu , Zijin Zhao , Kaixuan Yang , Pengtian Liu , Haolan Zhang , Jintai Li , Xiaoling Ma , Qi Yao , Yanming Sun , Fujun Zhang . 倍增型全聚合物光电探测器及其在光电容积描记传感器上的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2311021-. doi: 10.3866/PKU.WHXB202311021
7. [7]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
8. [8]
  Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
9. [9]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
10. [10]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
11. [11]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
12. [12]
  Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094
13. [13]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
14. [14]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
15. [15]
  Qingtang ZHANG , Xiaoyu WU , Zheng WANG , Xiaomei WANG . Performance of nano Li₂FeSiO₄/C cathode material co-doped by potassium and chlorine ions. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1689-1696. doi: 10.11862/CJIC.20240115
16. [16]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
17. [17]
  Ping Ye , Lingshuang Qin , Mengyao He , Fangfang Wu , Zengye Chen , Mingxing Liang , Libo Deng . 荷叶衍生多孔碳的零电荷电位调节实现废水中电化学捕集镉离子. Acta Physico-Chimica Sinica, 2025, 41(3): 2311032-. doi: 10.3866/PKU.WHXB202311032
18. [18]
  Zhuo Wang , Xue Bai , Kexin Zhang , Hongzhi Wang , Jiabao Dong , Yuan Gao , Bin Zhao . MOF模板法合成氮掺杂碳材料用于增强电化学钠离子储存和去除. Acta Physico-Chimica Sinica, 2025, 41(3): 2405002-. doi: 10.3866/PKU.WHXB202405002
19. [19]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
20. [20]
  Jingke LIU , Jia CHEN , Yingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(431)
HTML views(105)

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