Skip to main content
Log in

Thermal analysis of charge-transfer complex formed by nitrogen dioxide and substituted calix[4]arene

Characterization of complexation reversibility

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

Simultaneous thermal analysis with evolved gas analysis (STA-EGA) was used to study the ability of 1,3-alternate conformer of tert-butylcalix[4]arene with four n-propoxy substituents (1) to be applied for detection of nitrogen dioxide in reversible sensors. Solid calixarene 1 forms an intensively colored charge-transfer complex (CTC) with gaseous NO2/N2O4. Using the STA-EGA method, the nature and conditions of CTC bleaching were characterized, including the conditions of its reversible change of color from white to dark blue and back at CTC formation and decomposition. For this, the thermal stability of CTC and its regeneration products were studied. This, together with the ion thermograms for evolved gases, gives the information on the oxidation of 1 by nitrogen dioxide if present.

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

Access this article

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

Instant access to the full article PDF.

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

Similar content being viewed by others

References

  1. Yakimova LS, Ziganshin MA, Sidorov VA, Kovalev VV, Shokova EA, Tafeenko VA, Gorbatchuk VV. Molecular recognition of organic vapors by adamantylcalix[4]arene in QCM sensor using partial binding reversibility. J Phys Chem B. 2008;112:15569–75.

    Article  CAS  Google Scholar 

  2. Ziganshin MA, Yakimov AV, Safina GD, Solovieva SE, Antipin IS, Gorbatchuk VV. Nonregular structure–property relationships for inclusion parameters of tert-butylcalix[5]arene. Org Biomol Chem. 2007;5:1472–8.

    Article  CAS  Google Scholar 

  3. Hines JH, Wanigasekara E, Rudkevich DM, Rogers RD. Calix[4]arenes immobilized in a cellulose-based platform for entrapment and detection of NO x gases. J Mater Chem. 2008;18:4050–5.

    Article  CAS  Google Scholar 

  4. Ohira S-I, Wanigasekara E, Rudkevich DM, Dasgupta PK. Sensing parts per million levels of gaseous NO2 by a optical fiber transducer based on calix[4]arenas. Talanta. 2009;77:1814–20.

    Article  CAS  Google Scholar 

  5. Organo VG, Leontiev AV, Sgarlata V, Dias HVR, Rudkevich DM. Supramolecular features of calixarene-based synthetic nanotubes. Angew Chem Int Ed. 2005;44:3043–7.

    Article  CAS  Google Scholar 

  6. Rudkevich DM. Progress in supramolecular chemistry of gases. Eur J Org Chem. 2007;2007:3255–70.

  7. Rathore R, Lindeman SV, Rao KSSP, Sun D, Kochi JK. Guest penetration deep within the cavity of calix[4]arene hosts: the tight binding of nitric oxide to distal (cofacial) aromatic groups. Angew Chem Int Ed. 2000;39(12):2123–7.

    Article  CAS  Google Scholar 

  8. Zyryanov GV, Kang Y, Stampp SP, Rudkevich DM. Supramolecular fixation of NO2 with calix[4]arenes. Chem Commun. 2002;2792–3.

  9. Zyryanov GV, Rudkevich DM. Encapsulated reagents for nitrosation. Org Lett. 2003;5(8):1253–6.

    Article  CAS  Google Scholar 

  10. Huimei Y, Lingjun Q, Qinghong Zh, Danyu J, Changwei L. Application of TA–MS combined with PulseTA for characterization of materials. J Therm Anal Calorim. 2011;106:47–52.

    Article  Google Scholar 

  11. Zyryanov GV, Rudkevich DM. Toward synthetic tubes for NO2/N2O4: design, synthesis, and host-guest chemistry. J Am Chem Soc. 2004;126:4264–70.

    Article  CAS  Google Scholar 

  12. Safina GD, Validova LR, Ziganshin MA, Stoikov II, Antipin IS, Gorbatchuk VV. Using clathrate pseudopolymorphism for a single sensor detection of target component in the headspace of liquid mixture. Sens Actuators B. 2010;148:264–8.

    Article  Google Scholar 

  13. Karakuş ŐŐ, Çilgi GK, Deligőz H. Thermal analysis of two series mono- and di-azocalix[4]arene derivatives. J Therm Anal Calorim. 2011;105:341–7.

    Article  Google Scholar 

  14. Kang Y, Zyryanov GV, Rudkevich DM. Towards supramolecular fixation of NOX gases: encapsulated reagents for nitrosation. Chem Eur J. 2005;11:1924–32.

    Article  CAS  Google Scholar 

  15. Zyryanov GV, Kang Y, Rudkevich DM. Sensing and fixation of NO2/N2O4 by calix[4]arenas. J Am Chem Soc. 2003;125:2997–3007.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This study was supported by Russian Ministry of Education and Science (Contract No. 14.740.11.0377) and RFBR (11-03-01215-a). This study is dedicated to the memory of Prof. Dmitry M. Rudkevich.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Valery V. Gorbatchuk.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 973 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khabibullin, A.A., Safina, G.D., Ziganshin, M.A. et al. Thermal analysis of charge-transfer complex formed by nitrogen dioxide and substituted calix[4]arene. J Therm Anal Calorim 110, 1309–1313 (2012). https://doi.org/10.1007/s10973-011-2105-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-011-2105-5

Keywords

Navigation