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Anthraquinone Based Sensors for the Selective Detection of Cyanide Ion with Turn on Fluorescence with Logic Gate & Real Sample Applications

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Abstract

In recent years, there is an increasing interest in finding better and more efficient ways to detect CN− ions. Most of the anthraquinone-based probes show less fluorescence This paper presents the design and synthesis of a new anthraquinone based imine probe with good colorimetric sensing property and fluorescent turn on behavior toward CN− ion. Herein, we report a receptor with both colorimetric and fluorescent enhancement of cyanide ion in DMSO medium is synthesized. The synthesized receptor shows an immediate color change from orange to pink when cyanide is added; and it can be readily observed visually due to the presence of diverse p-conjugated systems in the receptor. These studies were confirmed by UV–Visible, PL studies, DFT, HRMS and 1H NMR titration. Moreover, this receptor shows 1:1 stoichiometry and micromolar detection limit. Further the receptor was applied to a real sample in finger millet (Eleusine Coracana) to detect the presence of cyanide ion. Moreover, the receptor is applicable toward INHIBITION, IMPLICATION logic gates with two input systems.

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References

  1. He XM, Yam VW (2011) A highly selective bifunctional luminescence probe for potassium and fluoride ions. Org Lett 13:2172–2175

    Article  CAS  PubMed  Google Scholar 

  2. Hu J, Lu JD, Ju Y (2012) A dual-responsive macrocycle based on glycyrrhetinic acid. Tetrahedron Lett 53:6705–6709

    Article  CAS  Google Scholar 

  3. Kim SK, Sessler JL (2010) Ion pair receptors. Chem Soc Rev 39:3784–3809

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Kulig KW (1991) Cyanide Toxicity U S Department of Health and Human Services Atlanta GA U.S. Dept. of Health & Human Services, Public Health Service, Agency for Toxic Substances and Disease Registry

  5. Baskin SL, Brewer TG, Sid ell FR, Tankafuji ET, Franz DR, (1997) Medical Aspects of Chemical and Biological Warfare. TMM Publications Washington 10:271–286

    Google Scholar 

  6. Baird C, Cann M (2005) Colin Baird’s Environmental Chemistry. Freeman, Macmillan, New York. Science 652

  7. Sumiya S, Doi T, Shiraishi Y, Hirai T (2012) Colorimetric sensing of cyanide anion in aqueous media with a fluorescein–spiropyran conjugate. Tetrahedron 68:690–696

    Article  CAS  Google Scholar 

  8. Rocklin RD, Johnson EL (1983) Determination of cyanide sulfide iodide and bromide by ion chromatography with electrochemical detection. Anal Chem 55:4–7

    Article  CAS  Google Scholar 

  9. Gang Q, Xianzhen L, Wang ZY (2009) Visible and near infrared chemosensor for colorimetric and ratiometric detection of cyanide. J Mater Chem 19:522–530

    Article  Google Scholar 

  10. Band AM, Heritag ID, Wallace GG, McCormick MJ (1982) Simultaneous determination of free sulfide and cyanide by ion chromatography with electrochemical detection. Anal Chem 54:582–585

    Article  Google Scholar 

  11. Zhaohai Z, Zhaolun F (1987) Spectrophotometric determination of total cyanide in waste waters in a flow-injection system with gas diffusion separation and preconcentration. Anal Chim Acta 198:1–345

    Google Scholar 

  12. Nie HM, Gon CB, Tang Q, Ma XB, Chow CF (2014) A colorimetric Schiff base chemosensor for CN− by naked-eye in aqueous solution. Dyes Pigm 106:74–80

    Article  CAS  Google Scholar 

  13. Batista RMF, Costa SPG (2007) Synthesis and ion sensing properties of new colorimetric and fluorimetric chemosensors based on bithienyl-imidazo-anthraquinone chromophores. Org Lett 9:3201–3204

    Article  CAS  PubMed  Google Scholar 

  14. Shan L, Guan-Min T, Chi Yung L, Yen Tzu C, Yao pin Y, (2009) ColorimetricAnion chemosensors based on anthraquinone: naked-eye detection of isomeric dicarboxylate and tricarboxylate anions. New J Chem 33:860–867

    Article  Google Scholar 

  15. Soosai D, Chi Rei Y (2012) A new selective chromogenic and fluorogenic sensor for citrate ion. Sens Actuators B 174:555–562

    Article  Google Scholar 

  16. Son YA, Kim SH (2015) The effect of terminal dimethyl and diethyl substituents on the J-aggregate-like molecular arrangement of bisazomethine dye molecules. Cryst Eng comm 17:7213–7226

    Article  Google Scholar 

  17. Kaur K, Saini R, Kumar A, Luxami V, Kaur N (2012) Chemodosimeters: an approach for detection and estimation of biologically and medically relevant metal ions, anions and thiols. Coord Chem Rev 256:1992–2028

    Article  CAS  Google Scholar 

  18. Xu Z, Chen X, Kim HN, Yoon J (2015) Sensors for the optical detection of cyanide ion. Chem Soc Rev 39:127–137

    Article  Google Scholar 

  19. Kumari N, Jha S, Bhattacharya S (2011) Colorimetric probes based on anthraimidazolediones for selective sensing of fluoride and cyanide ion via intramolecular charge transfer. J Org Chem 76:8215–8222

    Article  CAS  PubMed  Google Scholar 

  20. Li L, Liu F, Li H (2011) Selective fluorescent probes based on CN isomerization and intramolecular charge transfer (ICT) for zinc ions in aqueous solution. Spectro Chim Acta Part A 79:1688–1692

    Article  CAS  Google Scholar 

  21. Guo XP, Yan F, Yang S (2014) A novel ratiometric fluorescent mercury probe based on deprotonation-ICT mechanism. J Fluoresc 24:473–480

    Article  PubMed  Google Scholar 

  22. Sun Y, Liu Y, Chen M, Guo W (2009) Novel fluorescent and chromogenic probe for cyanide detection in water based on the nucleophilic addition of cyanide to imine group. Talanta 80:996–1000

    Article  CAS  PubMed  Google Scholar 

  23. Divya S, Paramjit K, Kamalijit S (2014) Strategies in detection of metal ions using dyes. Coord Chem Rev 265:125–154

    Article  Google Scholar 

  24. Xiao-Bin C, Hui L, Feng Z (2016) A simple chemosensor for the dual-channel detection of cyanide in water with high selectivity and sensitivity. RSC Adv 6:27130–27135

    Article  Google Scholar 

  25. Sourav M, Srikanta K, Debiprasad M (2015) Imidazolyl-pyreno-imidazole conjugate as cyanide sensor and set -reset memorized sequential logic device. Dalton Trans 44:15994–16012

    Article  Google Scholar 

  26. Angupillai S, Elango KP (2013) Spectral and DFT studies on simple and selective colorimetric sensing of fluoride ions via enhanced charge transfer using a novel signaling unit. Dyes Pigm 96:313–618

    Google Scholar 

  27. Kumar V, Kausik MP, Srivastav AK (2010) Thiourea based novel chromogenic sensor for selective detection of fluoride and cyanide anions in organic and aqueous media Anal Chim Acta 663:77–84

    CAS  PubMed  Google Scholar 

  28. Nirma M, Shubhrajyotsna B (2016) A modest colorimetric chemosensor for investigation of CN- in semi-aqueous environment with high selectivity and sensitivity. Sens Actuators B Chem 229:483–491

    Article  Google Scholar 

  29. Nirma M, Shubhrajyotsna B (2016) Selective and sensitive colorimetric sensor for CN− in the absence and presence of metal ions (Cu2+/Ni2+): mimicking logic gate behaviour. RSC Adv 6:71543–71549

    Article  Google Scholar 

  30. Fang W, Li W, (2014) Recent progress in the development of fluorometric and colorimetric chemosensors for detection of cyanide ions. Chem Soc Rev 43:4312–4324

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, K.Ramakrishnan College of Engineering (A), Tiruchirappalli, 621112, Tamil Nadu, India

    Ganesan Punithakumari

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  1. Ganesan Punithakumari
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Ganesan PunithaKumari write the manuscript and did all research in this manuscript.

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Correspondence to Ganesan Punithakumari.

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Punithakumari, G. Anthraquinone Based Sensors for the Selective Detection of Cyanide Ion with Turn on Fluorescence with Logic Gate & Real Sample Applications. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03397-8

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