Skip to main content

Advertisement

Log in

The Time-Resolved Fluorescence Stokes Shift of Cucurbit[6]Uril Complexes with a Pyridinium Styryl Dye

  • SHORT COMMUNICATION
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

The time-resolved Stokes shift of fluorescence of styryl dye, trans-4-[4-(dimethylamino)-styryl]-1-methylpyridinium iodide (DASPI), and its host-guest complexes with cucurbit[6]uril (CB[6]) was studied by up-conversion technique on a 5 ps time scale. In all cases, the solvation time correlation function – that describes relaxation of the fluorescent state - contains two components. The time constant of the first component, which is related to the vibrational relaxation of the dye cation, increases from 118 fs without CB[6] to 224 fs in the presence CB[6]. It suggests the production of CB[6] complexes to disturb the hydrogen-bond net in the vicinity of DASPI cation. The time constant of the second component, which is associated with solvation, changes from 0.81 ps without CB[6] to 1.15 ps in the presence of the cavitand. The observed increase can be related to the displacement of the dye cation deeper into CB[6] that allows considering DASPI-CB[6] complexes as a light-controlled molecular machine with a response time on the picosecond scale.

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

References

  1. Assaf KI, Nau WM (2015) Cucurbiturils: from synthesis to high-affinity binding and catalysis. Chem Soc Rev 44:394–418. https://doi.org/10.1039/c4cs00273c

    Article  PubMed  CAS  Google Scholar 

  2. Li Z, Sun S, Liu F, Yi P, Fan J, Song F, Peng X (2012) Large fluorescence enhancement of a hemicyanine by supramolecular interaction with cucurbit[6]uril and its application as resettable logic gates. Dyes Pigments 93:1401–1407. https://doi.org/10.1016/j.dyepig.2011.10.005

    Article  CAS  Google Scholar 

  3. Ivanov DA, Petrov NK, Nikitina EA, Basilevsky MV, Vedernikov AI, Gromov SP, Alfimov MV (2011) The 1:1 host−guest Complexation between cucurbit[7]uril and Styryl dye. J Phys Chem A 115:4505–4510. https://doi.org/10.1021/jp1123579

    Article  PubMed  CAS  Google Scholar 

  4. Van Der Meer MJ, Zhang H, Rettig W, Glasbeek M (2000) Femto- and picosecond fluorescence studies of solvation and non-radiative deactivation of ionic styryl dyes in liquid solution. Chem Phys Lett 320:673–680. https://doi.org/10.1016/S0009-2614(00)00258-X

    Article  Google Scholar 

  5. Glasbeek M, Zhang H (2004) Femtosecond studies of solvation and Intramolecular Configurational dynamics of Fluorophores in liquid solution. Chem Rev 104:1929–1954. https://doi.org/10.1021/cr0206723

    Article  PubMed  CAS  Google Scholar 

  6. Deligeorgiev T, Vasilev A, Kaloyanova S, Vaquero JJ (2010) Styryl dyes – synthesis and applications during the last 15 years. Color Technol 126:55–80. https://doi.org/10.1111/j.1478-4408.2010.00235.x

    Article  CAS  Google Scholar 

  7. Erbas-Cakmak S, Leigh DA, McTernan CT, Nussbaumer AL (2015) Artificial Molecular Machines. Chem Rev 115:10081–10206. https://doi.org/10.1021/acs.chemrev.5b00146

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  8. Petrov NK, Ivanov DA, Shandarov YA, Kryukov IV, Ivanov AA, Alfimov MV, Lobova NA, Gromov SP (2016) Ultrafast relaxation of electronically-excited states of a styryl dye in the cavity of cucurbit[n]urils (n = 6, 7). Chem Phys Lett 647:157–160. https://doi.org/10.1016/j.cplett.2016.01.063

    Article  CAS  Google Scholar 

  9. Turro NJ (1995) Supramolecular organic and inorganic photochemistry: radical pair recombination in micelles, electron transfer on starburst dendrimers, and the use of DNA as a molecular wire. Pure Appl Chem 67(1):199–208. https://doi.org/10.1351/pac199567010199

    Article  CAS  Google Scholar 

  10. Maroncelli M, Fleming GR (1987) Picosecond solvation dynamics of coumarin 153: the importance of molecular aspects of solvation. J Chem Phys 86:6221–6239. https://doi.org/10.1063/1.452460

    Article  CAS  Google Scholar 

  11. Horng ML, Gardecki JA, Papazyan A, Maroncelli M (1995) Subpicosecond measurements of polar solvation dynamics: Coumarin 153 revisited. J Phys Chem 99(48):17311–17337. https://doi.org/10.1021/j100048a004

    Article  CAS  Google Scholar 

  12. Huang Y, Cheng T, Li F, Huang C-H, Wang S, Huang W, Gong Q (2002) Photophysical studies on the mono- and Dichromophoric Hemicyanine dyes III. Ultrafast fluorescence up-conversion in methanol: twisting Intramolecular charge transfer and “two-state three-mode” model. J Phys Chem B 106:10041–10050. https://doi.org/10.1021/jp0208788

    Article  CAS  Google Scholar 

  13. Zhao L, Lustres JLP, Farztdinov V, Ernsting NP (2005) Femtosecond fluorescence spectroscopy by upconversion with tilted gate pulses. Phys Chem Chem Phys 7:1716–1725. https://doi.org/10.1039/B500108K

    Article  PubMed  CAS  Google Scholar 

  14. Bagchi B, Jana B (2010) Solvation dynamics in dipolar liquids. Chem Soc Rev 39:1936–1954. https://doi.org/10.1039/B902048A

    Article  PubMed  CAS  Google Scholar 

  15. Middleton CT, Cohen B, Kohler B (2007) Solvent and solvent isotope effects on the vibrational cooling dynamics of a DNA Base derivative. J Phys Chem A 111:10460–10467. https://doi.org/10.1021/jp0740595

    Article  PubMed  CAS  Google Scholar 

  16. Biedermann F, Uzunova VD, Scherman OA, Nau WM, De Simone A (2012) Release of high-energy water as an essential driving force for the high-affinity binding of cucurbit[n]urils. J Am Chem Soc 134(37):15318–15323. https://doi.org/10.1021/ja303309e

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

The work was supported by the Russian Science Foundation (project no. 14-13-00751) and in part by the Federal Agency of Scientific Organizations.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. A. Ivanov.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Petrov, N.K., Ivanov, D.A., Kryukov, I.V. et al. The Time-Resolved Fluorescence Stokes Shift of Cucurbit[6]Uril Complexes with a Pyridinium Styryl Dye. J Fluoresc 28, 883–887 (2018). https://doi.org/10.1007/s10895-018-2256-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-018-2256-x

Keywords

Navigation