Skip to main content
SpringerLink
Log in

Highly Sensitive Sensors for the Detection of Nitro Compounds Based on Pyrene Labeled Dendrons

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

In this paper, we describe the synthesis and characterization of four novel pyrene labeled compounds, some of them dendritic, which can act as potential sensors for the detection of nitro compounds in methanol solution. Methanol was selected as solvent due to its polar properties, which provide similar characteristics to water. The obtained pyrene labeled molecules (PyOH, Pytb, PyNK1OH and PyNK1tb) were studied by UV–Vis and steady state fluorescence spectroscopy. Their application as sensors has been tested with three different nitro compounds: nitrobenzene, 1-chloro-2,4-dinitrobenzene and nitromethane. PyOH and Pytb showed a detection concentration limit for the analyzed quenchers in the order of nM, making these compounds suitable for high-sensitive sensoring. PyNK1OH and PyNK1tb displayed high sensibility at µM concentration. All the sensors showed an accurate response towards quencher analytes.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. A. Azhdari Tehrani, L. Esrafili, S. Abedi, A. Morsali, L. Carlucci, D.M. Proserpio, J. Wang, P.C. Junk, T. Liu, Inorg. Chem. 56, 1446 (2017)

    Article  CAS  Google Scholar 

  2. Y. Sun, J. Liu, G. Frye-Mason, S. Ja, A.K. Thompson, X. Fan, Analyst (Lond) 134, 1386 (2009)

    Article  CAS  Google Scholar 

  3. X. Sun, Y. Wang, Y. Lei, Chem. Soc. Rev. 44, 8019 (2015)

    Article  CAS  Google Scholar 

  4. H. Ma, F. Li, Z. Zhang, M. Zhang, Sens. Actuators B 244, 1080 (2017)

    Article  CAS  Google Scholar 

  5. N. Hannink, S.J. Rosser, C.E. French, A. Basran, J.A. Murray, S. Nicklin, N.C. Bruce, Nat. Biotechnol. 19, 1168 (2001)

    Article  CAS  Google Scholar 

  6. R.D. Luggar, M.J. Farquharson, J.A. Horrocks, R.J. Lacey, X-Ray Spectrom. 27, 87 (1998)

    Article  CAS  Google Scholar 

  7. D.S. Moore, Rev. Sci. Instrum. 75, 2499 (2004)

    Article  CAS  Google Scholar 

  8. K. Håkansson, R.V. Coorey, R.A. Zubarev, V.L. Talrose, P. Håkansson, J. Mass Spectrom. 35, 337 (2000)

    Article  Google Scholar 

  9. A.S. Chajistamatiou, E.B. Bakeas, Talanta 151, 192 (2016)

    Article  CAS  Google Scholar 

  10. A.K.M. Jamil, A. Sivanesan, E.L. Izake, G.A. Ayoko, P.M. Fredericks, Sens. Actuators B 221, 273 (2015)

    Article  CAS  Google Scholar 

  11. J.M. Sylvia, J.A. Janni, J.D. Klein, K.M. Spencer, Anal. Chem. 72, 5834 (2000)

    Article  CAS  Google Scholar 

  12. E.S. Forzani, D. Lu, M.J. Leright, A.D. Aguilar, F. Tsow, R.A. Iglesias, Q. Zhang, J. Lu, J. Li, N. Tao, J. Am. Chem. Soc. 131, 1390 (2009)

    Article  CAS  Google Scholar 

  13. J. Mbah, K. Moorer, L. Pacheco-Londoño, S. Hernandez-Rivera, G. Cruz, Electrochim. Acta 88, 832 (2013)

    Article  CAS  Google Scholar 

  14. Y.-N. Gong, L. Jiang, T.-B. Lu, Chem. Commun. (Camb) 49, 11113 (2013)

    Article  CAS  Google Scholar 

  15. Q. Wang, Z. Li, D.-D. Tao, Q. Zhang, P. Zhang, D.-P. Guo, Y.-B. Jiang, Chem. Commun. (Camb) 52, 12929 (2016)

    Article  CAS  Google Scholar 

  16. F. Akhgari, H. Fattahi, Y.M. Oskoei, Sens. Actuators B 221, 867 (2015)

    Article  CAS  Google Scholar 

  17. S. Rochat, T.M. Swager, ACS Appl. Mater. Interfaces 5, 4488 (2013)

    Article  CAS  Google Scholar 

  18. A. Rose, Z. Zhu, C.F. Madigan, T.M. Swager, V. Bulović, Nature 434, 876 (2005)

    Article  CAS  Google Scholar 

  19. J.-S. Yang, T.M. Swager, J. Am. Chem. Soc. 120, 11864 (1998)

    Article  CAS  Google Scholar 

  20. L. Feng, H. Li, Y. Qu, C. Lü, Chem. Commun. (Camb) 48, 4633 (2012)

    Article  CAS  Google Scholar 

  21. H. Li, Y. Zhu, J. Zhang, Z. Chi, L. Chen, C.-Y. Su, RSC Adv. 3, 16340 (2013)

    Article  CAS  Google Scholar 

  22. H. Siu, J. Duhamel, Macromolecules 37, 9287 (2004)

    Article  CAS  Google Scholar 

  23. F.M. Winnik, Chem. Rev. 93, 587 (1993)

    Article  CAS  Google Scholar 

  24. B. Adhikari, J. Nanda, A. Banerjee, Chemistry (Easton) 17, 11488 (2011)

    CAS  Google Scholar 

  25. N. Maneelun, T. Vilaivan, Tetrahedron 69, 10805 (2013)

    Article  CAS  Google Scholar 

  26. K. Takemoto, M. Karasawa, M. Kimura, ACS Appl. Mater. Interfaces 4, 6289 (2012)

    Article  CAS  Google Scholar 

  27. K.P. Gan, M. Yoshio, T. Kato, J. Mater. Chem. C 4, 5073 (2016)

    Article  CAS  Google Scholar 

  28. E. Rodríguez-Alba, J. Ortíz-Palacios, E.G. Morales-Espinoza, M. Vonlanthen, B.X. Valderrama, E. Rivera, Synth. Met. 206, 92 (2015)

    Article  Google Scholar 

  29. M. Vonlanthen, A. Cevallos-Vallejo, E. Aguilar-Ortíz, A. Ruiu, P. Porcu, E. Rivera, Polymer (UK) 99, 13 (2016)

    Article  CAS  Google Scholar 

  30. D.P. Bhopate, P.G. Mahajan, K.M. Garadkar, G.B. Kolekar, S.R. Patil, RSC Adv. 4, 63866 (2014)

    Article  CAS  Google Scholar 

  31. G. Zaragoza-gala, M.A. Fowler, J. Duhamel, R. Rein, N. Solladie, E. Rivera, Languimir 28, 11195 (2012)

    Article  Google Scholar 

  32. G. Zaragoza-Galán, M.A. Fowler, J. Duhamel, R. Rein, N. Solladié, E. Rivera, Langmuir 28, 11195 (2012)

    Article  Google Scholar 

  33. T.C. Wang, N.A. Vermeulen, I.S. Kim, A.B.F. Martinson, J.F. Stoddart, J.T. Hupp, O.K. Farha, Nat. Protoc. 11, 149 (2016)

    Article  CAS  Google Scholar 

  34. S. Shanmugaraju, P.S. Mukherjee, Chem. Commun. (Camb) 51, 16014 (2015)

    Article  CAS  Google Scholar 

  35. M. Graetzel, J.K. Thomas, J. Am. Chem. Soc. 95, 6885 (1973)

    Article  CAS  Google Scholar 

  36. E. Miller, D. Jóźwik-Styczyńska, Colloid Polym. Sci. 285, 1561 (2007)

    Article  CAS  Google Scholar 

  37. J.M.G. Martinho, A.T. Reis e Sousa, M.E. Oliveira Torres, A. Fedorov, Chem. Phys. 264, 111 (2001)

    Article  CAS  Google Scholar 

  38. P. Beyazkilic, A. Yildirim, M. Bayindir, Nanoscale 6, 15203 (2014)

    Article  CAS  Google Scholar 

  39. M. Okamoto, F. Tanaka, J. Phys. Chem. A 106, 3982 (2002)

    Article  CAS  Google Scholar 

  40. M.W. Geiger, N.J. Turro, Photochem. Photobiol. 22, 273 (1975)

    Article  CAS  Google Scholar 

  41. X.-L. Ni, Y. Wu, C. Redshaw, T. Yamato, Dalton Trans 43, 12633 (2014)

    Article  CAS  Google Scholar 

  42. J.M.G. Martinho, J. Phys. Chem. 93, 6687 (1989)

    Article  CAS  Google Scholar 

  43. R.A. Beecroft, R.S. Davidson, D. Goodwin, J.E. Pratt, X.J. Luo, J. Chem. Soc. Faraday Trans. 2 82, 2393 (1986)

    Article  CAS  Google Scholar 

  44. C.M. Cardona, T. Wilkes, W. Ong, A.E. Kaifer, T.D. McCarley, S. Pandey, G.A. Baker, M.N. Kane, S.N. Baker, F.V. Bright, J. Phys. Chem. B 106, 8649 (2002)

    Article  CAS  Google Scholar 

  45. G.R. Newkome, Z. Yao, G.R. Baker, V.K. Gupta, J. Org. Chem. 50, 2003 (1985)

    Article  CAS  Google Scholar 

  46. G.R. Newkome, A. Nayak, R.K. Behera, C.N. Moorefield, G.R. Baker, G. Newkome, A. Nayak, R. Behera, C. Moorefield, G. Baker, G. Newkome, A. Nayak, R. Behera, C. Moorefield, G. Baker, J. Org. Chem. 57, 358 (1992)

    Article  CAS  Google Scholar 

  47. G.R. Newkome, K.K. Kotta, C.N. Moorefield, J. Org. Chem. 70, 4893 (2005)

    Article  CAS  Google Scholar 

  48. G.R. Newkome, C.D. Weis, C.N. Moorefield, I. Weis, Macromolecules 30, 2300 (1997)

    Article  CAS  Google Scholar 

  49. C.D. Schmidt, N. Lang, N. Jux, A. Hirsch, Chemistry (Easton) 17, 5289 (2011)

    CAS  Google Scholar 

  50. U. Hartnagel, D. Balbinot, N. Jux, A. Hirsch, Org. Biomol. Chem. 4, 1785 (2006)

    Article  CAS  Google Scholar 

  51. C. Ornelas, R. Lodescar, A. Durandin, J.W. Canary, R. Pennell, L.F. Liebes, M. Weck, Chemistry (Easton) 17, 3619 (2011)

    CAS  Google Scholar 

  52. F. Spänig, M. Ruppert, J. Dannhäuser, A. Hirsch, D.M. Guldi, J. Am. Chem. Soc. 131, 9378 (2009)

    Article  Google Scholar 

  53. D.J. Berry, Y. Ma, J.R. Ballinger, R. Tavaré, A. Koers, K. Sunassee, T. Zhou, S. Nawaz, G.E.D. Mullen, R.C. Hider, P.J. Blower, Chem. Commun. (Camb) 47, 7068 (2011)

    Article  CAS  Google Scholar 

  54. E. Rivero-Buceta, E.G. Doyagüez, I. Colomer, E. Quesada, L. Mathys, S. Noppen, S. Liekens, M.-J. Camarasa, M.-J. Pérez-Pérez, J. Balzarini, A. San-Félix, Eur. J. Med. Chem. 106, 34 (2015)

    Article  CAS  Google Scholar 

  55. H. Destecroix, C.M. Renney, T.J. Mooibroek, T.S. Carter, P.F.N. Stewart, M.P. Crump, A.P. Davis, Angew. Chem. Int. Ed. Engl. 54, 2057 (2015)

    Article  CAS  Google Scholar 

  56. T. Zhou, H. Neubert, D.Y. Liu, Z.D. Liu, Y.M. Ma, X.L. Kong, W. Luo, S. Mark, R.C. Hider, J. Med. Chem. 49, 4171 (2006)

    Article  CAS  Google Scholar 

  57. N. Dib, L. Fernández, L. Otero, M. Santo, M. Calderón, M. Martinelli, M. Strumia, J. Inclusion Phenom. Macrocycl. Chem. 82, 351 (2015)

    Article  CAS  Google Scholar 

  58. L. Fernandez, M. Calderón, M. Martinelli, M. Strumia, H. Cerecetto, M. González, J.J. Silber, M. Santo, J. Phys. Org. Chem. 21, 1079 (2008)

    Article  CAS  Google Scholar 

  59. C. Ornelas, R. Pennell, L.F. Liebes, M. Weck, Org. Lett. 13, 976 (2011)

    Article  CAS  Google Scholar 

  60. M.C. Strumia, A. Halabi, P.A. Pucci, G.R. Newkome, C.N. Moorefield, J.D. Epperson, J. Polym. Sci. Part A 38, 2779 (2000)

    Article  CAS  Google Scholar 

  61. G.R. Newkome, K.S. Yoo, C.N. Moorefield, Des. Monomers Polym. 5, 67 (2002)

    Article  CAS  Google Scholar 

  62. A. Amin, R. Sarkar, C.N. Moorefield, G.R. Newkome, Polym. Eng. Sci. 53, 2166–2174 (2013)

    CAS  Google Scholar 

  63. S. Zhao, A. Ramette, G.-L. Niu, H. Liu, N.-Y. Zhou, FEMS Microbiol. Ecol. 70, 159 (2009)

    Article  Google Scholar 

  64. P. Paramasivan, C. Lai, C. Pickard, M. Ardern-Jones, E. Healy, P.S. Friedmann, Br. J. Dermatol. 162, 594 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank Miguel A. Canseco Martínez and Gerardo Cedillo for their technical assistance in the characterization of the sensing compounds. We are also grateful to CONACYT (Project 253155) and PAPIIT (Project IN-100316) for financial support. Mireille Vonlanthen is grateful to the Swiss National Science Foundation for a postdoctoral fellowship (P2ZHP2-148707). A. Ruiu, P. Porcu and I. González-Méndez thank Posgrado en Ciencias Químicas UNAM and CONACYT for scholarship and financial support, respectively.

Author information

Authors and Affiliations

  1. Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior Ciudad Universitaria, C.P. 04510, Ciudad de México, Mexico

    Andrea Ruiu, Mireille Vonlanthen, Pasquale Porcu, Israel Gonzalez-Méndez & Ernesto Rivera

Authors
  1. Andrea Ruiu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mireille Vonlanthen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pasquale Porcu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Israel Gonzalez-Méndez
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ernesto Rivera
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ernesto Rivera.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1888 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ruiu, A., Vonlanthen, M., Porcu, P. et al. Highly Sensitive Sensors for the Detection of Nitro Compounds Based on Pyrene Labeled Dendrons. J Inorg Organomet Polym 28, 448–456 (2018). https://doi.org/10.1007/s10904-017-0686-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-017-0686-6

Keywords

Search

Navigation