Skip to main content
SpringerLink
Log in

Theoretical study of thiourea derivatives as chemosensors for fluoride and acetate anions

  • Articles
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

The different interactions between a chemosensor, 1-(naphthalen-2-yl)-3-(6-nitrobenzothiazol-2-yl)-thiourea (1), and F−, acetate (AcO−), Cl−, and Br− anions have been investigated theoretically at the B3LYP/6-31+G(d,p) level with the basis set superposition error (BSSE) correction. It was found that the high selectivity of compound 1 for F− can be ascribed to the ability of the anion to deprotonate the N-H fragment of the host sensor, while the chemosensor also has a strong affinity for AcO− by virtue of the formation of a hydrogen-bonded complex. Intramolecular charge transfer (ICT) causes the colorimetric signaling of compound 1 after interaction with F−/AcO−. A study of substituent effects suggested that the O/NH- and O/S-substituted derivatives are also expected to be promising candidates for chromogenic F−/AcO− chemosensors.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Dey KR, Wong BM, Hossain MA. Rational design of a macrocycle-based chemosensor for anions. Tetrahedron Lett, 2010, 51: 1329–1332

    Article  CAS  Google Scholar 

  2. Qu Y, Hua J, Tian H. Biomimetic cationic polyannulation reaction catalyzed by Bi(OTf)3: Cyclization of 1,6-dienes, 1,6,10-trienes, and aryl polyenes. Organic Lett, 2010, 12: 3320–3323

    Article  CAS  Google Scholar 

  3. Deng Y, Chen Y, Cao D, Liu Z, Li G. A cationic triarylborane as water-tolerant fluorescent chemosensor for fluoride anions. Sensors Actuat B-Chem, 2010, 149: 165–169

    Article  Google Scholar 

  4. Rhee HW, So JC, Sang HY, Yong OJ, Hun HP, Pinto RM, Cameselle JC, Sandoval FJ, Roje S, Han K, Chung DS, Suh J, Hong JI. A bifunctional molecule as an artificial flavin mononucleotide cyclase and a chemosensor for selective fluorescent detection of flavins. J Am Chem Soc, 2009, 131: 10107–10112

    Article  CAS  Google Scholar 

  5. Li JQ, Li XY. Multichannel photoinduced intramolecular electron-transfer excitations in a bis-naphthalimide spermine conjugate by time-dependent density functional theory. J Phys Chem A, 2007, 111: 13061–13068

    Article  CAS  Google Scholar 

  6. Fabbrizzi L, Licchelli M, Rabaioli MG, Tagllietai A. The design of luminescent sensors for anions and ionisable analytes. Coord Chem Rev, 2000, 205: 85–108

    Article  CAS  Google Scholar 

  7. Qing GY, He YB, Zhao Y, Hu CG, Liu SY, Yang X. Calix[4]arene-based chromogenic chemosensor for the α-phenylglycine anion: Synthesis and chiral recognition. Eur J Org Chem, 2006, 6: 1574–1580

    Article  Google Scholar 

  8. Cametti M, Rissanen K. Recognition and sensing of fluoride anion. Chem Commun, 2009, 20: 2809–2829

    Article  Google Scholar 

  9. Zhang SW, Swager TM. Fluorescent detection of chemical warfare agents: Functional group specific ratiometric chemosensors. J Am Chem Soc, 2003, 125: 3420–3421

    Article  CAS  Google Scholar 

  10. Gunnlaugsson T, Davis AP, O’Brien JE, Glynn M. Fluorescent sensing of pyrophosphate and bis-carboxylates with charge neutral PET chemosensors. Org Lett, 2002, 4: 2449–2452

    Article  CAS  Google Scholar 

  11. Misra A, Shahid M, Dwivedi P. An efficient thiourea-based colorimetric chemosensor for naked-eye recognition of fluoride and acetate anions: UV-vis and 1H NMR studies. Talanta, 2009, 80: 532–538

    Article  CAS  Google Scholar 

  12. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JAJr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Wallingford CT: Gaussian Inc., 2009

    Google Scholar 

  13. Jin R. Theoretical study of thiazole derivatives as chemosensors for fluoride anion. J Fluorine Chem, 2011, 132: 907–914

    Article  CAS  Google Scholar 

  14. Jin R, Zhang J. Theoretical study of chemosensor for fluoride and phosphate anions and optical properties of the derivatives of 2-(2-hydroxyphenyl)-1,3,4-oxadiazole. Chem Phys, 2011: 380, 17-23

  15. Jin R, Zhang J. Theoretical investigation of chemosensor for fluoride anion based on amidophthalimide derivatives. Theor Chem Acc, 2009, 124: 225–234

    Article  CAS  Google Scholar 

  16. Simon S, Duran M, Dannenberg JJ. How does basis set superposition error change the potential surfaces for hydrogen-bonded dimers? J Chem Phys, 1996, 105: 11024–11031

    Article  CAS  Google Scholar 

  17. Cornard JP, Lapouge C. Absorption spectra of caffeic acid, caffeate and their 1:1 complex with Al(III): Density functional theory and time-dependent density functional theory investigations. J Phys Chem A, 2006, 110: 7159–7166

    Article  CAS  Google Scholar 

  18. Sidorkin VF, Doronina EP, Chipanina NN, Aksamentova TN, Shainyan BA. Bifurcate hydrogen bonds. Interaction of intramolecularly H-bonded systems with Lewis bases. J Phys Chem A, 2008, 112: 6227–6234

    Article  CAS  Google Scholar 

  19. Nagaraju M, Narahari Sastry G. Effect of alkyl substitution on H-bond strength of substituted amide-alcohol complexes. J Mol Model, 2011, 17: 1801–1816

    Article  CAS  Google Scholar 

  20. Karabıyık H, Sevinçek R, Petek H, Aygün M. Aromaticity balance, π-electron cooperativity and H-bonding properties in tautomerism of salicylideneaniline: The quantum theory of atoms in molecules (QTAIM) approach. J Mol Model, 2011, 7: 1295–1309

    Article  Google Scholar 

  21. Bader RFW. A bond path: A universal indicator of bonded interactions. J Phys Chem A, 1998, 102: 7314–7323

    Article  CAS  Google Scholar 

  22. Bader RFW. A quantum theory of molecular structure and its applications. Chem Res, 1991, 91: 893–928

    Article  CAS  Google Scholar 

  23. Abramov YA. On the possibility of kinetic energy density evaluation from the experimental electron-density distribution. Acta Crystallogr A, 1997, 53: 264–272

    Article  Google Scholar 

  24. Bader RFW. Atoms in molecules: A quantum theory, Oxford UK: Clarendon Press, 1994

    Google Scholar 

  25. Espinosa E, Molins E, Lecomte C. Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities. Chem Phys Lett, 1998, 285: 170–173

    Article  CAS  Google Scholar 

  26. Steiner T, Desiraju GR. Distinction between the weak hydrogen bond and the van der Waals interaction. Chem Commun, 1998, 8: 891–892

    Article  Google Scholar 

  27. Steiner T. The hydrogen bond in the solid state. Angew Chem Int Ed, 2002, 41: 48–76

    Article  CAS  Google Scholar 

  28. Parra RD, Ohlssen J. Cooperativity in intramolecular bifurcated hydrogen bonds: An ab initio study. J Phys Chem A, 2008, 112: 3492–3498

    Article  CAS  Google Scholar 

  29. Hobza P, Havlas Z. Blue-shifting hydrogen bonds. Chem Rev, 2000, 100: 4253–4264

    Article  CAS  Google Scholar 

  30. Amendola V, Esteban-Gómez D, Fabbrizzi L, Licchelli M. What anions do to N-H-containing receptors. Acc Chem Res, 2006, 39: 343–353

    Article  CAS  Google Scholar 

  31. Nakanishi W, Hayashi S, Narahara K. Atoms-in-molecules dual parameter analysis of weak to strong interactions: Behaviors of electronic energy densities versus Laplacian of electron densities at bond critical points. J Phys Chem A, 2008, 112: 13593–13599

    Article  CAS  Google Scholar 

  32. Forés M, Duran M, Solà M, Adamowicz L. Excited-state intramolecular proton transfer and rotamerism of 2-(2’-hydroxyvinyl)benzimi-dazole and 2-(2′-hydroxyphenyl)imidazole. J Phys Chem A, 1999, 103: 4413–4420

    Article  Google Scholar 

  33. Helal A, Rashid MHO, Choi CH, Kim HS. Chromogenic and fluorogenic sensing of Cu2+ based on coumarin. Tetrahedron, 2011, 67: 2794–2802

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, 024000, China

    RuiFa Jin & WeiDong Sun

Authors
  1. RuiFa Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. WeiDong Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to RuiFa Jin.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jin, R., Sun, W. Theoretical study of thiourea derivatives as chemosensors for fluoride and acetate anions. Sci. China Chem. 55, 1428–1434 (2012). https://doi.org/10.1007/s11426-012-4660-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-012-4660-4

Keywords

Search

Navigation