204
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Chromogenic detection of fluoride, dihydrogen phosphate, and arsenite anions based on 2,4-dinitrophenyl hydrazine receptors: spectral and electrochemical study

, , &
Pages 534-549 | Received 20 Apr 2022, Accepted 05 Jun 2022, Published online: 07 Jul 2022

References

  • Kaushik R, Ghosh A, Singh A, et al. Selective detection of cyanide in water and biological samples by an off-the-shelf compound. ACS Sens. 2016;1(10):1265–1271.
  • Pati C, Ghosh K. A 1,8-naphthalimide-pyridoxal conjugate as a supramolecular gelator for colorimetric read out of F− ions in solution, gel and solid states. New J Chem. 2019;43(6):2718–2725.
  • Kaur N, Kaur G, Fegade UA, et al. Anion sensing with chemosensors having multiple –NH recognition units. Trends Anal Chem. 2017;95:86–109.
  • Sharma D, Kuba A, Thomas R, et al. Acetate selective fluorescent turn-on sensors derived using vitamin B6 cofactor pyridoxal-5-phosphate. Spectrochim Acta - Part A Mol Biomol Spectrosc. 2016;157:110–115.
  • Pangannaya S, Kaur A, Mohan M, et al. Synthesis and spectral investigation of colorimetric receptors for the dual detection of copper and acetate ions: application in molecular logic gates. Supramol Chem. 2017;29(8):561–574.
  • Guan R, Chen H, Cao F, et al. Two fluorescence turn-on chemosensors for cyanide anions based on pyridine cation and the boronic acid moiety. Inorg Chem Commun. 2013;38:112–114.
  • Devendhiran T, Kumarasamy K, Lin MC, et al. Synthesis and physical studies of coumarin-based chemosensor for cyanide ions. Inorg Chem Commun. 2021;134:108951.
  • Kaur N, Gauri G. Anthraquinone appended chemosensors for fluorescence monitoring of anions and/or metal ions. Inorganica Chim Acta. 2022;536(March):120917.
  • Gale PA. Amidopyrroles: from anion receptors to membrane transport agents. Chem Commun. 2005; 132 (30):3761–3772.
  • Raju V, Kumar RS, Kumar SKA, et al. A ninhydrin–thiosemicarbazone based highly selective and sensitive chromogenic sensor for Hg2+ and F− ions. J Chem Sci. 2020;132(1):1.
  • Ghosh K, Ali SS, Joardar S. Design and synthesis of azaindole heterocycle decorated new scaffold in fluorometric sensing of F− and H2PO4−. J Heterocycl Chem. 2020;57(10):3558–3565.
  • Gale PA. From anion receptors to transporters. Acc Chem Res. 2011;44(3):216–226.
  • Pati C, Chattopadhyay AP, Ghosh K. Diamino malenonitrile-linked naphthalimide in selective sensing of F−, CN−, Hg2+ and Cu2+ under different experimental conditions. Supramol Chem. 2020;32(7):403–413.
  • Raza R, Panja A, Ghosh K. Diaminomaleonitrile-functionalized gelators in F-/CN-Sensing, phase-selective gelation, oil spill recovery and dye removal from water. New J Chem. 2020;44(25):10275–10285.
  • Ghosh A, Jose DA, Kaushik R. Anthraquinones as versatile colorimetric reagent for anions. Elsevier;2016.
  • Wagh YB, Tayade KC, Kuwar A, et al. Exploration of highly selective fluorogenic ‘on–off” chemosensor for H2PO4− ions: ICT-based sensing and ATPase activity profiling. Luminescence. 2020;35(3):379–384.
  • Fang H, Gan Y, Wang S, et al. A selective and colorimetric chemosensor for fluoride based on dimeric azulene boronate ester. Inorg Chem Commun. 2018;95:17–21.
  • Xu Y, Wang Y, Zhao S, et al. A novel fluorescence chemodosimeter for fluoride anions in aqueous solution based on siloxane-aurone moiety. Inorg Chem Commun. 2017;78:52–55.
  • Chen W, Liang H, Wen X, et al. Synchronous colorimetric determination of CN−, F−, and H2PO4− based on structural manipulation of hydrazone sensors. Inorganica Chim Acta. 2022;532:120760.
  • Ghosh S, Alam MA, Ganguly A, et al. Selective colorimetric sensing of fluoride ion and its use for in situ cyclization of the sensor. Inorganica Chim Acta. 2015;429:39–45.
  • Yuan X, Zhao CX, Lu YX, et al. A novel naphthalimide-based probe for highly sensitive and selective recognition of fluoride ion. J Photochem Photobiol A Chem. 2018;361:41–47.
  • Snowden TS, Anslyn EV. Anion recognition: synthetic receptors for anions and their application in sensors. Curr Opin Chem Biol. 1999;3(6):740–746.
  • Shang XF, Li J, Lin H, et al. anion recognition and sensing of ruthenium(ii) and cobalt(ii) sulfonamido complexes. J Chem Soc Dalt Trans. 2009;(12):2096–2102.
  • Sahu S, Sikdar Y, Bag R, et al. Visual detection of fluoride ion based on ICT mechanism. Spectrochim Acta - Part A Mol Biomol Spectrosc. 2019;213:354–360.
  • Singh P, Barjatiya M, Dhing S, et al. Evidence suggesting that high intake of fluoride provokes nephrolithiasis in tribal populations. Urol Res. 2001;29(4):238–244.
  • Bencini A, Lippolis V. Metal-based optical chemosensors for CN− detection. Environ Sci Pollut Res. 2016;23(24):24451–24475.
  • Suganya S, Velmathi S. Simple azo-based salicylaldimine as colorimetric and fluorescent probe for detecting anions in semi-aqueous medium. J Mol Recognit. 2013;26(6):259–267.
  • Maity SB, Bharadwaj PK. A chemosensor built with rhodamine derivatives appended to an aromatic platform via 1,2,3-triazoles: dual detection of aluminum (III) and Fluoride/Acetate Ions. Inorg Chem. 2013;52(3):1161–1163.
  • Pramanik K, Ghosh P, Dey D, et al. chelator probe with exceptionally high stokes shift for selective detection of oac– with red emission: application as a biosensor. ChemistrySelect. 2018;3(4):1151–1156.
  • Orojloo M, Arabahmadi R, Naderi F, et al. A novel receptor for detection of zn2+ metal ion and F−, H2PO4− and AcO− Anions in aqueous media: a DFT study. Chem Pap. 2018;72(3):719–729.
  • Zheng ZB, Duan ZM, Ma YY, et al. Highly sensitive and selective difunctional ruthenium (ii) complex-based chemosensor for dihydrogen phosphate anion and ferrous cation. Inorg Chem. 2013;52(5):2306–2316.
  • Sen S, Mukherjee M, Chakrabarty K, et al. Cell permeable fluorescent receptor for detection of H 2 PO 4- in aqueous solvent. Biomol Chem. 2013;11(9):1537–44.
  • Bao X, Zhou Y, Song B. Recognition and sensing properties of a quinazolinylaminothiourea-based anion receptor in non-aqueous and aqueous CH3 CN–DMSO medium. Sens Actuators B Chem. 2012;171-172:550–555.
  • Xu Z, Singh NJ, Kim SK, et al. Induction-driven stabilization of the anion-π interaction in electron-rich aromatics as the key to fluoride inclusion in imidazolium-cage receptors. Chem A Eur J. 2011;17(4):1163–1170.
  • Xiong S, Nanda Kishore MV, Zhou W, et al. Recent advances in selective recognition of fluoride with macrocyclic receptors. Coord Chem Rev. 2022;461:214480.
  • Zhou Y, Zhang JF, Yoon J. Fluorescence and colorimetric chemosensors for fluoride-ion detection. Chem Rev. 2014;114(10):5511–5571.
  • Eun JC, Byung JR, Young JL, et al. Visible Colorimetric Fluoride Ion Sensors. Org Lett. 2005;7(13):2607–2609.
  • Singh A, Sahoo SK, Trivedi DR. Colorimetric anion sensors based on positional effect of nitro group for recognition of biologically relevant anions in organic and aqueous medium, insight real-life application and DFT studies. Spectrochim Acta - Part A Mol Biomol Spectrosc. 2018;188:596–610.
  • Amendola V, Esteban-Gómez D, Fabbrizzi L, et al. what anions do to N-H-containing receptors. Acc Chem Res. 2006;39(5):343–353.
  • Liu WX, Jiang YB. N-Amidothiourea based PET Chemosensors for anions. Org Biomol Chem. 2007;5(11):1771–1775.
  • Singh A, Tom S, Trivedi DR. Aminophenol based colorimetric chemosensor for naked-eye detection of biologically important fluoride and acetate ions in organo-aqueous medium: effective and simple anion sensors. J Photochem Photobiol A Chem. 2018;353:507–520.
  • Cui Y, Mo HJ, Chen JC, et al. Anion-selective interaction and colorimeter by an optical metalloreceptor based on ruthenium (ii) 2,2′-biimidazole: hydrogen bonding and proton transfer. Inorg Chem. 2007;46(16):6427–6436.
  • United States Environmental Protection Agency. Arsenic and clarifications to compliance and new source monitoring rule: a quick reference guide. Off Water. 2001;(4606):2–3.
  • Wang M, Xu J, Liu X, et al. A highly selective pyrene based “off–on” fluorescent chemosensor for cyanide. New J Chem. 2013;37(12):3869–3872.
  • Cullen WR, Reimer KJ. Arsenic speciation in the environment. Chem Rev. 1989;89(4):713–764.
  • Fontàs C, Vera R, Batalla A, et al. A novel low-cost detection method for screening of arsenic in groundwater. Environ Sci Pollut Res. 2014;21(20):11682–11688.
  • Tchounwou PB, Yedjou CG, Patlolla AK, et al. Molecular, clinical and environmental toxicology volume 3. Environ Toxicol. 2012;101(2):82–116
  • Saha J, Roy AD, Dey D, et al. Development of arsenic(v) sensor based on fluorescence resonance energy transfer. Sens Actuators B Chem. 2017;241(v):1014–1023.
  • Shumlas SL, Singireddy S, Thenuwara AC, et al. Oxidation of arsenite to arsenate on birnessite in the presence of light. Geochem Trans. 2016;17(1):1.
  • Agou T, Sekine M, Kobayashi J, et al. Detection of biologically important anions in aqueous media by dicationic azaborines bearing ammonio or phosphonio groups. Chem A Eur J. 2009;15(20):5056–5062.
  • Sakai R, Barasa EB, Sakai N, et al. Colorimetric detection of anions in aqueous solution using poly(phenylacetylene) with sulfonamide receptors activated by electron withdrawing group. Macromolecules. 2012;45(20):8221–8227.
  • Anand T, Sivaraman G, Iniya M, et al. Aminobenzohydrazide based colorimetric and “turn-on” fluorescence chemosensor for selective recognition of fluoride. Anal Chim Acta. 2015;876:1–8.
  • Mukherjee S, Paul AK. Pyrene based chemosensor for selective sensing of fluoride in aprotic and protic environment. J Fluoresc. 2015;25(5):1461–1467.
  • Li Z, Wang S, Xiao L, et al. An efficient colorimetric and absorption ratiometric anion sensor based on a simple azo-azomethine receptor. Inorganica Chim Acta. 2018;479:148–153.
  • Bhardwaj VK, Hundal MS, Hundal G. A tripodal receptor bearing catechol groups for the chromogenic sensing of f− ions via frozen proton transfer. Tetrahedron. 2009;65(41):8556–8562.
  • Khanmohammadi H, Rezaeian K. Naked-eye detection of inorganic fluoride in aqueous media using a new azo-azomethine colorimetric receptor enhanced by electron withdrawing groups. RSC Adv. 2014;4(2):1032–1038.
  • Pangannaya S, Thimaradka V, Trivedi DR. Electroanalytical and spectral investigation of organic receptors as colorimetric and absorption ratiometric anion chemosensor. Supramol Chem. 2018;30(2):103–114.
  • Patil P, Ajeya KV, Bhat MP, et al. Real-time probe for the efficient sensing of inorganic fluoride and copper ions in aqueous media. ChemistrySelect. 2018;3(41):11593–11600.
  • Hou P, Chen S, Song X. A colorimetric and fluorescent probe for fluoride ions based on 6-acetyl-2-naphthol. Luminescence. 2014;29(5):423–426.
  • Thimaradka V, Pangannaya S, Mohan M, et al. Hydrazinylpyridine based highly selective optical sensor for aqueous source of carbonate ions: electrochemical and DFT studies. Spectrochim Acta - Part A Mol Biomol Spectrosc. 2018;193:330–337.
  • Srikala P, Tarafder K, Shetty AN, et al. Insights into the electrooptical anion sensing properties of a new organic receptor: solvent dependent chromogenic response and DFT studies. RSC Adv. 2016;6(78):74649–74653.
  • Duvenhage MM, Ntwaeaborwa M, Visser HG, et al. Determination of the optical band gap of alq3 and its derivatives for the use in two-layer oleds. Opt Mater (Amst). 2015;42:193–198.
  • Suganya S, Park JS, Velmathi S. Visual sensing of aqueous anions by c2-symmetric chemosensor and its application in real sample analysis. Sensors Actuators B Chem. 2014;190:679–684.
  • Chauhan K, Singh P, Kumari B, et al. Synthesis of new benzothiazole Schiff base as selective and sensitive colorimetric sensor for arsenic on-site detection at ppb level. Anal Methods. 2017;9(11):1779–1785.
  • Singh A, Mohan M, Trivedi DR. Design and synthesis new colorimetric receptors for naked-eye detection of biologically important fluoride and acetate anions in organic and arsenite in aqueous medium based on ICT mechanism: DFT study and test strip application. Spectrochim Acta Part A Mol Biomol Spectrosc. 2020;225:117522.
  • Singh A, Nishith U, Trivedi DR. Spectroscopic studies of colorimetric receptors for detection of biologically important inorganic F−, AcO− and H2PO4− anions in organo-aqueous medium: real-life application. Inorg Chem Commun. 2020;115:107874.
  • Shao J, Yu X, Lin H, et al. Colorimetric recognizing of biologically important anions based on anion-induced tautomerism of the sensor. J Mol Recognit. 2008;21(6):425–430.
  • Singh A, Girish Gowda R, Trivedi DR. Substituent effect on colorimetric detection of biologically and environmentally relevant anions: insight in real-life applications. Spectrochim Acta Part A Mol Biomol Spectrosc. 2019;219:517–529.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.